One amazing Tuscany Road Trip to discover an unforgettable scenery!

Tuscany Road Trip

A car is all you need! 🙂 for an unforgettable Tuscany road trip….Tuscany offers a rich territory not just in terms of traditions and culture, but also in terms of its varied geographical composition; hills, plains, mountain ranges, islands and seacoast. The beautiful lush landscape of Tuscany with its extensive green fields, hill towns and cypresses is probably the thing for which the region is best known.

Tuscany is in fact the ideal setting for scenic drives! Driving through Tuscany is a sight in itself, and is the perfect solution to really experience the atmosphere of this unique land.

The best thing is to avoid motorways, and enjoy the Tuscan scenery on winding roads in the countryside and panoramic routes far from the traffic; then driving becomes a truly rewarding experience.

Driving Tours of Tuscany: Tuscany Road Trip Itinerary

There are two main driving routes crossing Tuscany that we highly suggest you go through; both are famous for their sensational scenery and their beautiful sights, the Via Chiantigiana, and the Via Cassia.

Tuscany road trip 1: Via Chiantigiana, the scenic drive through Chianti: Scenic Drives from Florence

The Via Chiantigiana, SR222 (see Map at the end of the page), that connects Florence to Siena through the stupendous countryside of the Chianti region, is one of the most beautiful routes of Italy.

Well known for its vineyards, cellars and extensive views over a pristine landscape, Chianti is the place where to get lost among centuries of history, hidden treasures and excellent food and wines.

Leaving Florence and heading south, you are soon surround by the typical Tuscan countryside and by small villages up the hills, like Strada in Chianti and Chiocchio.

Here are also intriguing medieval castles like the ones of Meleto and Verrazzano, also producing a fine Chianti Classico wine that you can taste, not too much though if you’re the driver 🙂

The castle of Montefioralle was home to the enigmatic Monna Lisa, portrayed by Leonardo da Vinci. This small charming hamlet is actually worth a visit for its atmosphere lost in time.

Continuing south we get to Greve in Chianti, heart of the Chianti Classico wine production, where to find lots of tempting food shops sheltered by lovely arcades, and a whole Museum devoted to wine.

Past Greve you find yourself in the nice hill town of Panzano in Chianti, the perfect place to enjoy some great local food, like the superb Florentine steak by the whimsical butcher Mario Cecchini.

After Panzano you go through woods inhabited by wild boars, hares and squirrels, until you get to the old military outpost of Castellina in Chianti, one of the nicest towns in the area.

Here was built the Consorzio del Chianti Classico, that in 1984, gets the DOCG brand for local wines.

Taking a little detour you might want to visit the villages of Radda and Gaiole where to find excellent restaurants, wineries for tastings, and workshops. Now make your way to the beautiful Castle of Brolio, where the recipe of the Chianti Classico wine was born, and where the ghost of the Baron Bettino Ricasoli is believed to wander at night, according to the legend.

Curvy roads then follow one after the other, until you get to the splendid Siena.

The Via Chiantigiana is an extraordinary road riding through times.

Tuscany Road Trip 2: Via Cassia, ancient driving route running across centuries

The Via Cassia, SS2, (see Map below) is a very ancient Roman road connecting Florence and Siena to Rome through the Val d’Orcia.  For most of its route the Via Cassia coincides with the historic Via Francigena, that the pilgrims were used to cross on their spiritual journey from Canterbury to Rome.

This secular route passes through the most spectacular countryside of Tuscany and probably of all of Italy; the type of landscape found in the most common postcards about Tuscany.

The Val d’Orcia is a unique combination of history, art, and scenic beauty, declared a Unesco World Heritage Site.

Start your itinerary driving south of Siena along the SR2 Via Cassia, so entering the Val d’Arbia and the fascinating Crete Senesi territory; wheat fields, undulating hills, isolated cypress trees and a mostly deserted landscape. We pass through the nice villages of Monteroni d’Arbia and Buonconvento. Buonconvento is a very nice medieval town encircled by walls, worth a visit.

Val d’Orcia Tour: Scenic Drives from Siena

Past Buonconvento, shortly after Torrenieri, the Via Cassia faces the inimitable landscape of the Val d’Orcia near San Quirico d’Orcia. Here begins the most spectacular stretch of this historic road.

East and west the Cassia, lie sensational villages and hamlets atop scenic hills.

San Quirico d’Orcia is one of the oldest villages in the area, and is perfect to take a pleasant walk, especially at the Horti Leonini, a wonderful example of Italian garden.


10 Km east of San Quirico is Pienza, the jewel of the Val d’Orcia, enchanting hill town with incredible 15th century architecture and a fabulous location. The views from the walls surrounding the village will leave you breathless.

Pienza is the perfect place to stop for lunch; wine and cheese specialties are not to be missed, while the many craft shops are all to discover.

15 kilometers west of San Quirico is the magnificent Montalcino, splendid medieval hill town with thick walls and an imposing fortress, famous for its Brunello red wine. Here are many wine bars and wine shops. The walkable walls of the castle will give you a breathtaking panorama on the countless vineyards surrounding Montalcino.

Returning on the Via Cassia, south of San Quirico, you find the lovely small town of Bagno Vignoni, with its magnificent square of water and its thermal baths. From the thermal waters of Bagno Vignoni we continue the road trip to the foot of the ancient volcano Monte Amiata up to Bagni di San Filippo, another thermal village where the water flows out from the earth at about 50 degrees.

During the ride is impossible not to notice a perfectly preserved fortress that dominates the entire Val d’Orcia, just 20 kilometers from Montalcino; the village of Rocca d’Orcia is a sight not to be missed. The Rocca a Tentennano dominates the entire valley with an unforgettable and never ending panorama.

We can then leave the Cassia for a while to get to the spectacular Fortress of Radicofani from which to enjoy another stunning vista all over the valley and all its beauty.

The drive then continue towards Rome…with many more sights to enjoy along the way. For additional scenic drives through Tuscany, check here.

Map of the Via Chiantigiana route through Chianti

Map of the Via Cassia, scenic route from Siena to Rome


  • Nitin Rameshchandra ha detto:

    Hi Elena, We were planning this vacation in Umbria and Tuscany. (July 4 drive from Rome to Orvieto (halt 2 hours) – via Todi (halt 1 hr) – Deruta (halt 1 hr) – Passignano sul trasimeno (arrive around 1845 hrs). July 5 – drive Passignano – Gubbio ( halt 1.5 hrs) – Assissi (halt 2 hrs) – Spoleto ( halt 1 hr) – Spello (halt 1 hr) return to Passignano around 2030 hrs. July 6 – Passignano – Cortona (halt 2 hrs) – Perugia (halt 4 hrs) return to passignano by 1830 hrs. July 7 – drive from Passignano – Montepulciano (halt 2 hrs) – Montalcino (halt 2 hrs) – Sienna (stay overnight) reaching by 1715 hrs. July 8 – sight seeing in Siena. July 9 – Sienna – your via Chiantigani route to Florence in reverse. Night Florence. July 10 – Florence. July 11 – Florence – Pisa – Lucca – Florence (by train). July 12 – Florence. July 13 – Florence to Venice by train. Does this sound doable and nice according to you. Thanks in advance. Hope to get a reply soon.

    • elena nacci ha detto:

      Hi Nitin,
      Thanks for your message.
      Your itinerary through Umbria and Tuscany is fantastic! My compliments 🙂 It’s doable and covers some of the best sights of both regions.
      Maybe the first day is a bit full of things to see, but doable anyway. This blog post about a road trip from Rome to Tuscany can be of further inspiration.
      On July 7 before heading toward Montalcino you might stop for a brief walk in Pienza’s beautiful historic center.
      On July 9 departing from Siena, you may consider a brief detour to reach the famous San Gimignano, ancient villages by medieval towers, and then head east to ride on the Chiantigiana road in Castellina in Chianti. If you consider San Gimignano is too far (45 minutes) you can stop in the wonderful Monteriggioni walled town.
      For any further advice just get back!
      Enjoy your summer trip to Italy!

  • Monika ha detto:

    Hi, how much time do I need if I wanted to follow your itinerary to Tuscany? Thanks

    • elena nacci ha detto:

      Hi Monika!
      Thanks for your message.
      Glad you like my itinerary. If you have in mind both routes, both the Chiantigiana and the Via Cassia up to Radicofani, then you might need from 4 days to one week according to how many places you stop along the way. The most logical way would be to stay 1 night in Florence, then head south through Chianti where to pass about 2 nights, then continue on to Siena where to stay one night or 2, and finally drive south of Siena on the Cassia and stay in Val d’Orcia for about 2 days. Much depends on what are your must see places in Tuscany and the time you have.

      Let me know if I can be of further help,
      Ciao from Florence.

  • Patrick ha detto:

    Hello Elena, Needed your advice. Travelling with oldish parents and two young kids (3yrs) and not sure where to base in Tuscany for 2 nights( 15th & 16th June). I’ve been to San G earlier and enjoyed it but did not get to see the rolling hills that so many have been talking about to the south Tuscany.

    Considering we are a mixed group want to make sure its comfortable driving and looking around the place as well. Further if I did think of Pienze to the south will June still have the green soft hill views etc ? I would not want something too steep of a climb. Any advise will be very much appreciated
    Many Thanks

    • elena nacci ha detto:

      Ciao Patrik,
      The Val d’Orcia hills are very gentle and the landscape is spectacular; you might note however, that there can be curvy roads mainly when you can to go uphill to reach the fantastic hill towns of the area. But nothing to worry about! Driving in this unique territory is a pleasure! The area near Pienza and particularly Bagno Vignoni can both make a perfect base! and June still has the green soft hill views 🙂

      Find some info on the best sights to visit in Val d’Orcia here.

      I remain at your disposal for any further help,
      Enjoy your trip,

  • Ricardo Mariani ha detto:

    Buon giorno Elena, I will be traveling to Rome July 10th through the 18th. My first time to Rome. I would like to spend a few days in Tuscany and probably make a stop in Montalcino and sleep for a night. Can you recommend an inexpensive place to stay or somewhere nearby maybe even two nights.

    Grazia e rividerci,


  • Michela ha detto:


    My husband and I have left 2 full days to explore Tuscany in our itinerary. We will be leaving from Florence the morning of the first day and will need to be in Rome at the end of the last day. Our goal is to enjoy beautiful countryside, some vineyards and small towns along the way. We are unsure about our timeline and where we should aim to “just drive on through” vs slow down and enjoy the sights. I realize ideally we would do this drive in up to 4-6 days to enjoy the entire route. Do you have any recommendations for us as we plan?

    Thank you!

    • elena nacci ha detto:

      2 Days is not quite a lot of time, but you could still drive on the same routes I suggest on the post and have fun!

      Day 1: Leave Florence early in the morning and take the Via Chiantigiana admiring the landscape, you might stop in 2 villages in Chianti like Greve and Castellina in Chianti and taste wine at some winery; then proceed towards the beautiful Siena for lunch time. Siena is a must see, spend some time there. Leave Siena and just drive on through the Crete Senesi before reaching the amazing Val d’Orcia, where I would actually spend the evening and the following morning to enjoy the sights. I would spend the night in the unique thermal village of Bagno Vignoni, that is on your way to Rome, there are great restaurants all around the famous ancient Renaissance pool.

      Day 2: Start to explore the area, the Val d’Orcia, leaving Bagno Vignoni: Montalcino, Pienza, and Montepulciano. In order to spare time, once in Montepulciano you might consider running on the fast A1 Motorway to Rome, maybe with a stop to visit the stunning Orvieto. Taking the fast motorway will allow you to spend more time visiting the sights of the Val d’Orcia.

      Feel free to contact me again for any further help,

  • Marian ha detto:

    Hi Elena,
    My husband and I will be arriving in Florence on June 3 and driving to a B&B outside of Empoli to spend 4 nights. We hope to spend the days exploring the towns around that area. We then will travel to Siena for 3 nights and do the same around that area. We are thinking about visiting 1 maybe 2 towns a day, having lunch there and then returning to our B&B. We will then drive back to Florence drop off the car and stay 3 nights in Florence before flying home on the 13th June.
    Can you suggest the best towns and villages to explore and some very good restaurants?
    Thank You,

    • elena nacci ha detto:

      Hello Marian,
      I’m happy to give some tips for your upcoming Tuscan holiday 🙂
      Among the day trips to make from Empoli, I recommend:
      Vinci, lovely small village atop a hill where is the very interesting Museum of Leonardo da Vinci.
      – Pisa, where is the spectacular Square of the Miracles and the Leaning Tower
      – Lucca, beautiful town encircled by thick medieval walls and offering a pleasing walkway right on its walls. Lucca is also the perfect place to enjoy excellent local food, try the restaurant Gli Orti di via Elisa.
      – Certaldo and San Gimignano, this last one not to be missed

      You might visit Chianti, one of the most scenic areas of Tuscany, when leaving Empoli to head towards Siena or even better the day you’re driving back to Florence. In Chianti some of my favorite places to eat fantastic food are the Osteria di Passignano and Badia a Coltibuono.

      And here is my list of the best restaurants in Florence.

      Siena is a fantastic medieval art town, among its best restaurants are Ristorante La Taverna di San Giuseppe and Ristorante Bagoga.

      Siena is a great starting point to explore Tuscany, from there do not miss Monteriggioni, the Crete Senesi and particularly the wonderful villages of the Val d’Orcia area, so scenic a place! Pienza, Montalcino, and Montepulciano are full of great places to eat. I love Otsteria Baccus in Pienza, famous for its delicious pecorino cheese.

      Find a full list of all the day trips to enjoy from Siena.
      I remain at your disposal,
      Enjoy your Tuscan stay!

  • George ha detto:

    Hi Elene,

    My girlfriend and I will be travelling to Italy in September and would like to drive from Florence to Rome to enjoy Tuscany. Our trip lasts only 13 days so we are trying to make a plan that allow us to see and experience the cities and enjoy the Tuscany and at least spend a few days in the Amalfi coast. Our idea is to explore the Italian fields, food, architecture and wine, of course.

    1Sun: Venice p.m.
    2 Monday: Venice
    3 Tuesday: Venice / Florence pm
    4 Wednesday: Florence
    5 Thursday: Pisa/Lucca Daytrip – Florence p.m.
    6 Friday: Day 1 Road Trip to Rome (Stops????)
    7 Saturday: Day 2 Road Trip (Stops????)
    8 Sunday: Day 3 Road Trip (Stops) / Rome p.m.
    9 Monday: Rome
    10 Tuesday: Rome
    11 Wednesday: Capri
    12 Thursday: Capri/Amalfi
    13 Friday: Amalfi / Naples p.m.
    14 Naples flight out 7:00 a.m.

    Do you think is possible to make a memorable 3 day Tuscany road trip? What are your recommendations? Due to our tight itinerary in the Amalfi, we would consider cutting the road trip to 2 days if you think it is necessary to enjoy the Amalfi. Thank you for your suggestions.

    • elena nacci ha detto:

      Hi George,
      Thanks a lot for getting in touch and sorry for the delay!
      The drive from Florence to Rome is full of many incredible sights to visit! I see your tour is starting in Venice, a must see! My suggested tour of Italy actually include the sights you mention from Venice to the splendid Amalfi Coast.

      Now let’s study your plan:
      2 nights in Venice are ok, I imagine you are taking a fast train that will then take you to the city center of Florence, from where you will visit both Lucca and Pisa on a day trip by train. When you’re ready to leave Florence with a rented car, the stops I suggest on your way to Rome are: Chianti, San Gimignano, Siena, the Val d’Orcia, Orvieto, Civita di Bagnoregio and finally Rome. I would spend 1 night either in Chianti or in Siena after you’ve visited both Chianti and San Gimignano, and the other night in the heart of the beautiful Val d’Orcia.
      Take a look at this road trip from Rome to Florence, just follow it conversely.
      The time to spend in Rome is ok, then I suppose you will first reach the Amalfi Coast, and then also visit Capri. I’m in love with this area of Italy! I think it’s possible to make a memorable 3 day Tuscany road trip, 2 days would be not enough. Follow my road itineraries:-)
      Of course Tuscany and Amalfi Coast are very different from each other, so much depends on your personal preferences as to pass one day more here or there,
      Have a great Italian trip!

  • karen ha detto:

    Hello Elena,

    I have read your recommendations. I wanted to know how long the first route would take? I have two days in the area.
    Any recommendations?
    Thanks in advance!:)

    • elena nacci ha detto:

      Hi Karen,
      Here I am 🙂
      The first route, with no stops along the way, takes about 2 hours’ time. As you will have 2 days in the area, I suggest you take our time, and stop all the times you like to visit a hill town or a winery. A good idea would be to spend one night in the heart of Chianti, and then visit also Siena or other sights in the area on the following day,
      Have a great time 🙂

  • Ivann ha detto:

    Hi Elena. We need to drive from Siienna to Soreento in one day! Will we be able to go via the Via Cassia route you have described?
    Thanks for the help

    • elena nacci ha detto:

      Hi Ivann,

      The fast A1 Highway from Siena to Rome takes around 2 hours and half while the Via Cassia around 4 hours and half. Honestly I wouldn’t recommend you take the Cassia. You need to add other 3 hours or more to reach Sorrento from Rome. Driving on the A1 you can still enjoy some stops that are on your way, like the beautiful Montepulciano and Orvieto.

      Enjoy your holiday!

  • Laura ha detto:

    Hie Elena,

    I love your blog and it seems that you are very knowledgeable. My husband and I have 7 nights to stay in Italy. Being that we do not drink at all do you think that Tuscany is a good choice or should we do the Almalfi coast? I know that they are two different trips entirely but we are doers and need to keep ourselves busy.
    Looking forward to your expert answer.


    • elena nacci ha detto:

      Dear Laura,
      I’m very happy you love my blog 🙂

      You’re right when you say that Tuscany and the Amalfi Coast are very different! Both are beautiful however, so you may well decide to pass some days in each location. I love the Amalfi Coast; its beautiful scenery and lemon trees right facing the sea, the breathtaking views, the delicious food and all the local specialities. The same can be said of Tuscany, that is not just wine! Every region of Italy has its own famous wine labels; there are many also in the Amalfi Coast.

      Tuscany offers a lot in terms of hill towns, fascinating villages, unique treasures of art, varied scenic landscape, even seacoast, and of course great food. Here is a list of the top attractions in Tuscany for instance, while here is a list for things to do in Tuscany, so be sure you’ll never get bored:-)

      Please contact me again for any other question,
      Enjoy planning your holiday,

  • Jenny ha detto:

    Hi Marion We are planning a holiday to Italy in May we want to spend 5 days touring the tuscanny hill side villages and wineries. We are think about making are base at San donanto. Will be having a couple of days in Florence and also Sienna so will do day tous from there but would like help planning day trips on back roads around Tuscanny We are in our early 70. Need your help.

    • elena nacci ha detto:

      Hi Jenny!
      Thanks for contacting me!
      I think you mean the nice hill village of San Donato in Poggio, in the Chianti wine area. Enjoying a central location in Tuscany it’s ideal for making day tours. Chianti itself is full of back roads, simply follow secondary roads to hill towns, wineries, and castles. An example is the visit to the beautiful Badia a Passignano. Both moving west towards San Gimignano and Volterra or south down to Siena and the Val d’Orcia all roads are curvy and very scenic.

      In the blog there’s a post with a list of the best day trips I recommend having Chianti your home base. Take a look and for any other suggestions, just get back to me,

      Have a nice day,

  • Mary Appel ha detto:

    Hi Elena – We have travelled to the typical hilltowns of Lucca , Sienna , San Gimigano etc. We will be renting an apt. in Montelpulciano for 5 nights and would like to visit some unusual hilltowns as photography is our favorite thing to focus on, not restaurants etc. Can you give a more detailed idea of a drive through Val Dorcia, Pienza etc, using scenic roads ( I know they all are) and also what can we see if we drive to La Foce (can we visit gardens etc.) Thanks so much for all the info on this site. Mary A

    • elena nacci ha detto:

      HI Mary,
      thanks for coming here 🙂

      I love Montepulciano and I think it is an ideal home base to go exploring great Tuscan sights. Among the unusual hilltowns to visit from there, I recommend the sugestive village of Bagno Vignoni, Monticchiello, Rocca d’Orcia, and further south the amazing villages of Pitigliano, Sorano and Sovana. Also find my suggestions for the day trips to make from Montepulciano to be found at the end of the article.

      All drives in Val d’Orcia are actually scenic, as the road from Pienza to reach the near Monticchiello or the one from Montalcino to reach the Abey of Sant’Antimo. The road leading to La Foce gardens, that can be visited, is particularly scenic and lined by cypress trees, take a look at the pics here.

      Let me know if I can be of further help,
      Enjoy your trip!

  • Jon ha detto:

    Hello Elena,

    Glad to have stumbled upon your blog as we have really enjoyed your insights to get the most of the region. My wife and I are making castellina our home base to explore the countryside for 3 nights before heading up to Florence for 2 nights. Are there a couple good day loops you could recommend? We want what most people look for when visiting… Small hilltop towns, great scenery and excellent food/wine! Thanks in advance for any tips. Going next week for what it’s worth.


    • elena nacci ha detto:

      Hi Jon,
      Hope it’s not too late to answer you!

      Castellina is one of the most charming hill towns in Chianti 🙂 Among some of the best day trips in the area I’d recommend a visit to the tiny and characteristic hill village of Montefioralle, where a fine Chianti wine is produced, a visit with lunch at the scenic Badia di Passignano osteria and ancient winery, the Castle of Brolio, and possibly some other hill town like Gaiole or Radda in Chianti. Here I speak about Chianti, take a look,

      Enjoy your stay in Tuscany!

      • Jon ha detto:

        Great suggestions and we will certainly work these towns into our daily plans. We leave for Tuscany tomorrow so your response was timely! Thanks again, Jon

  • Martha ha detto:

    Hi Elena,
    We are planning to travel in October to Italy, spending 3 days in Rome and 4 days in Tuscany. Would you recommend for us to rent the car in rome and move up towards Florence and then return by train to Rome, or go by train to Florence and rent there and move south to go back to Rome.. Any way, we need to go back to Rome.


    • elena nacci ha detto:

      Hi Martha,
      It’s really quite the same. I would probably rent the car in Rome and then move up north towards Florence. Where are you staying in Tuscany? This road trip from Rome to Tuscany can be helpful and give you some ideas.

      Let me know if you need any more tips,

  • Sunen ha detto:

    Hi Elena,
    We will be traveling from Rome to The Mall in Leccio via A1 for time saving purposes. Do you recommend any restaurants or traditional Tuscan places where we may stop to have a quick lunch on this route? We will be staying in San Gimignano a few days and will be taking day trips from here. Upon our return to Rome we will be taking the scenic road Via Cassia back. Thank you so much for your blog, it has been very helpful for planning our vacation.

    • elena nacci ha detto:

      Dear Sunen,
      Glad to hear my blog was helpful in planning your vacation 🙂

      On your way from Rome to the Mall in Leccio I would stop in Montepulciano for your lunch. This hill top town is incredibly beautiful and has lots of great places to eat, also for a quick lunch. You can in fact opt for a wine bar serving excellent local dishes and excellent wine like Osteria del Borgo di Montepulciano or a good osteria like Osteria del Conte.
      I imagine you’ve already seen my suggested day trips from San Gimignano 🙂 and the ones on the scenic road Via Cassia back to Rome.

      Let me know if I can be of further help.

      Have a great time in Italy,

  • JJ ha detto:

    Ciao Elena,

    Your blog has wonderful information, and I enjoy it very much.

    I will be in Tuscany next month and will be driving from Siena to Florence and need to arrive by 15:00. I am interested in your scenic drive through Chianti, Via Chiantigiana, and I was hoping to see many of the highlights you recommend. Since I need to be in Florence by 15:00, what time do you recommend I leave Siena? Also, what places do you recommend I absolutely must see or I may skip since my time is limited? I am an avid photographer, but I am not a big wine drinker. I enjoy visiting small villages and the peacefulness of the countryside. Consequently, I could skip drinking wine in villages while driving through the Chianti, unless the location is very picturesque 😉


    • elena nacci ha detto:

      Ciao JJ,
      Happy to give some advice 🙂
      You could leave quite early in the morning like at 8 am, so you will have time to drive on the Via Chiantigiana and also take your time.

      Your first stop maybe in Monteriggioni, northwest of Siena; though not on the Chiantigiana road, this beautiful walled hamlet is unique for its intact medieval architecture, it’s very picturesque and offers fantastic views from its ancient bastions.
      Then retuning on the Chiantigiana road Radda and Gaiole in Chianti may be worth visiting, as is the lovely Castellina in Chianti. You might skip Panzano and Greve in Chianti and proceed to visit the small but picturesque village of Montefioralle before continuing on to reach Florence. On your way, if you see you’re running out of time, you may skip another village between Radda and Gaiole.

      Feel free to contact me again,

      • JJ ha detto:

        Ciao Elena, grazie for the wonderful suggestions. I will follow your itinerary and try to see as many places as possible but make sure I arrive on time in Florence.

        I will rent a car in Pisa and drive through Tuscany. I plan to purchase a map, Touring Club Italiano Toscana, when I rent my car in Pisa. Is it easy to purchase these maps or recommend a better Tuscany map in Pisa? Where may I buy one of these?

        If you like, I can share some pictures with you of my trip through Tuscany. The pictures you post on your blog are very beautiful and inspiring 🙂


        • elena nacci ha detto:

          Ciao JJ,
          Here I am 🙂

          A map of the Touring Club will work great, you can easily find maps everywhere, especially at kiosks. You can buy it right in Pisa.

          I would be really happy if you share some of your pictures 🙂 you’re also welcome to tell about your trip and see your story published in this section of the blog!

          I’m here for any other info needed,
          Have a nice day!

          • JJ ha detto:

            Ciao Elena, thanks for sharing your tips and I had a great time in Tuscany. That was probably the highlight of my entire trip 🙂

            If you would like me to share a few pictures, then where would you like me to post them or do you prefer I email them directly to you? The picture file sizes are a bit big, which are about 30MB each. However, I could shrink the file size, if that’s too big for you. Email me directly with instructions, if that’s easier.

            Let me know if you would like me to share a few pictures and thanks again for everything. Keep up the great work!


          • elena nacci ha detto:

            Ciao JJ,
            I’m so happy to hear from you and that you had a great time in Tuscany 🙂

            I’d be more than happy to receive your pictures by email at; you can send them through

            If you like the idea you’rr also welcome to tell something about your Italian holiday and see it published here on the blog together with some of your pics.
            a presto,

  • John S ha detto:

    We’re in Sienna for two nights and then have two free nights. Best to go to SG or Bagno Vignoni, or both? Or Montepulciano? Thanks! Love your blog: it’s inspiring and helpful

    • elena nacci ha detto:

      Hi John,
      so happy you love my blog 🙂
      As you have 2 more free nights, I would visit both. The day you’re leaving Siena you can go visit San Gimignano and stay there the morning and maybe have lunch there, and then head south to reach Bagno Vignoni as well as Montepulciano. The villages of the Val d’Orcia area small so you can see more of them. Also Pienza is stunning!
      Feel free to contact me again,
      Enjoy your stay!

  • Sandra T. ha detto:

    Ciao Elena,
    First of all congratulations for such a nice blog, full of interesting tips!
    I’m planning to spend one week in Tuscany with my husband. We will travel to Pisa early in the morning in September 5th and return back to Madrid on Sept. 12th. We are planning to rent a car either in Pisa or in Florence and travel around. Our idea is to explore the Italian medieval cities, the countryside…, and we love food, architecture and wine, of course!
    Do you have any recommendations for a memorable one week trip? Do you think that we have enough time to visit Tuscany and also make it to Cinque Terre? What are your tips? Thank you for your suggestions.
    Have a nice day!

    • elena nacci ha detto:

      Ciao Sandra,
      I’m happy you like my blog 🙂

      I think you will also have time to visit the Cinque Terre. as you’re arriving to Pisa, you can soon reach the near Cinque Terre and spend there the first night. The following day, maybe in the afternoon, I would start the itinerary to discover the beautiful Tuscany.

      How to plan one week on Tuscany? In this blog post I give tips on how to make the best of Tuscany in 7 days; the must see visits should particularly include Florence, Chianti, San Gimignano, Siena, and the stunning Val d’Orcia, so full of beautiful medieval cities and a unique countryside. Where to stay? you might choose 1 or 2 different locations to base yourself. The first in Chianti or San Gimignano, and the second in Val d’Orcia.

      Let me know if you need any more suggestion, I’l be happy to help 🙂

  • Pao ha detto:

    Hi Elena,

    You have a great blog, congratulations!!! I love it.

    I was wondering if you could help me out organising a 2 nights 3 day trip from/to Rome around Tuscany. I’m planing going on July 15th to 17th. I’m considering to do your first route from Rome to Siena and stay the first night there. What I’m not sure about is which route take from Siena to Rome considering that I still have 2 days and 1 night ahead. I’m sure that with your wise advices I could have an even greater time around Tuscany. I will really appreciate any suggestion.

    Cheers!! 😀

    • elena nacci ha detto:

      Hi Pao,
      Very happy you like my blog 🙂 thank you!

      So you start by driving on the Via Cassia from Rome to Siena that passes through the stunning Val d’Orcia and the Crete Senesi. The following day I would pass some of your time visiting the beauty of Siena, and then go visit the beautiful villages of San Gimignano and Monteriggioni. Never been to Florence? In alternative you may soon head to Florence from Siena, and pass a the night there. Then from Florence stat your way back to Rome passing from the amazing sights of Cortona, the Trasimeno Lake, Orvieto and Civita.

      I’m sure my post dedicated to a road trip from Rome to Tuscany and back will be of great help 🙂

      Have a great holiday,

      • Pao ha detto:

        Hi Elena,

        Thank you soon much for your kind reply, I really appreciate it!! 😀

        Yes, I’ve been in Florence many times and that’s exactly why I would like to stay just around Tuscany, not really Florence.

        I think the best would be to opt for the tour you suggested until Monteriggioni, and may be sleep over there? Is there any other adventurous and exciting route from there to Rome?



        • elena nacci ha detto:

          Here I am Pao 🙂
          You might certainly sleep near Monteriggioni or Siena, and then from there decide to continue to Rome passing thorough the Crete Senesi, the Val d’Orcia and then south with a deviation toward west to visit the amazing villages of Pitigliano, Sorano, and Sovana.

          Have a nice weekend,

  • Nancy ha detto:

    Hi Elena,
    My husband and I will be arriving in Pisa on Monday August 24th. We are staying at Piombino until 16th September. Could you please suggest places that we should visit, a cooking class plus any other tours or attractions. We intend hiring a car but haven’t organised that yet.
    Love reading your holiday blog and looking forward to spending time in Tuscany.
    Cheers Nancy

    • elena nacci ha detto:

      Dear Nancy,
      Thanks for your message 🙂
      Renting a car is the best thing you can do for visiting and exploring Tuscany.
      As you are in Piombino, I suggest you don’t miss visiting the beautiful Elba Island and the fascinating seacoast running south passing from Castiglione della Pescaia to reach the splendid Monte Argentario.If you move inland, I suggest you visit Massa Marittima, the suggestive villages of the Val d’Orcia Park, Siena, Florence, San Gimignano and all of Tuscany main attractions. Some destinations like Florence are farther than others but worth to visit.

      As for the cooking class, where would you like to have it?
      Have a great holiday,

  • John ha detto:

    Hello Elena

    My wife and I are in the initial stages of planning a trip to Tuscany/Emilia-Romagna in October 2016 and need some advice. We hope to miss most of the crowds with that timing, but my first question is can we get good pictures then? I understand we may not see the lush, green hills of summer but still hope to see good color and interesting landscapes. We’re planning on three weeks, which is adjustable by a few days pending your advice. We will take daily driving tours and would like advice on the number of days we should spend in each area and where to stay as a single base of operations in each area. We expect to fly into Rome and rent a car and then spend several days and nights in: Cinque Terre; Parma/Modena/Bologna; Florence/Chianti; and Siena/San Gimignano, visiting as many towns as we can. We started with four days at each but that was arbitrary, and we don’t want to stay too long in one if there is more to see in another. Can you offer specific recommendations?

    We have two additional concerns. Your Val d’Orcia tour got us thinking. Are we making a mistake by not spending fewer days in Tuscany and more in Umbria? The second concern is what are the “don’t miss” locations in each of the areas? One of our fears is driving past a spectacular location due to ignorance. Admittedly, the above is very general, but thanks for any thoughts you can give us.

    • elena nacci ha detto:

      Hi John,
      Happy to receive your message!
      In October you can still be able to see interesting landscapes, but with autumnal colors, so a different landscape from the one you see on postcards.
      3 weeks is really enough time to see the destinations you mention. Have you planned spending at least 2 days in Rome? I think 4 days at each destination are ok; 3 or 4 to see Parma/Modena/Bologna, 4 to see Florence/Chianti, and 4 or more to see Siena/San Gimignano/Val d’Orcia.
      This 2 weeks itinerary of Tuscany can be helpful you focus on the most fascinating sights to see across Tuscany.
      Also visiting Umbria in addition to Tuscany/Emilia-Romagna? Umbria is actually beautiful and boasts really so many amazing hill towns, Orvieto, Assisi, Perugia, Spello, Gubbio. You may spend some days in the beautiful Cortona, on the border betwen Tuscany and Umbria and explore the attractions of both regions, take a look here for that.
      Read though the links and get back to me at anytime for any other question,
      Have a nice weekend,

      • John ha detto:

        Thanks very much for your recommendations. We can start building an itinerary now adding the villages you mentioned. I’m looking forward to getting some “nontraditional” pictures so October may be perfect.


  • Kumar ha detto:

    Hi Elena,
    Great suggestions and write up!
    Wife and I are visiting Rome for a short trip of four days in first week of September. One day we are renting a motorcycle from Rome to ride a scenic route.

    Do you think Rome to Siena to Rome can be done in one full day with stops to see historic and scenic places?


  • Will ha detto:

    Ciao Elena
    My wife and I are driving from Pisa to Follonica. We see there is a motorway S1 and also the main road SR439. Do you have any thoughts, suggestions for a nice relaxing drive. We will be staying at Castiglione Della Pescaia for one week in an agriturismo in September. Or would be good to get the train from Pisa to Follonica and then hire a car in Follonica itself..


    Will & Claudia

    • elena nacci ha detto:

      Dear Will & Claudia,
      thanks a lot for getting in touch,
      If you take the fast motorway you can reach Follonica from Pisa in about 1 hour and 20 minutes. If you like driving and would like to try a scenic route you may take the SR439 passing through Volterra and then Massa Marittima, both real gems of Tuscany.

      In any case I would reach Follonica by car,

      I remain at your disposal,

  • michelle ha detto:

    We want to take a motorcycle through tuscany. We are going in the beginning of november and i know the roads are curvy think it would be OK? Have three days there i though the first day stay in florence cause it might be a half day. Then rent motorcycle for two days. I want to get the most of two days Wine food and scenery are very important. Any suggestions?

    • elena nacci ha detto:

      Hi Michelle,
      thanks for contacting me.
      In Tuscany roads are curvy, but that’s actually the pleasure of driving a motorcycle:-) However, the beginning of november can be cold and rainy, so I honestly would rent drive a car.

      I would do Florence the first day, then direct towards Chianti and San Gimignano on the second day, and on your 3rd day I would go to visit Siena and possibly some small village south of Siena, like Pienza or Montepulciano in Val d’Orcia. Be sure to find wine, food, and scenery, especially in Chianti and in Val d’Orcia.

      Have a great holiday,

  • Randy ha detto:


    We will be arriving on the 16th of September into Rome and driving up to an Agriturismo outside of San Gimignano. We will be there for 5 days before heading back to Rome. We would like to drive to Cortona and back through Montalcino stopping in Montepulciano, Pienza, and see the Abbey di S. Antimo. Should we break this up or can this be done in a day? What other sites should we see while on that excursion as well as others from San Gimignano for day trips? We have been to Florence and Siena wouldn’t mind a stop in Siena again. Any Suggestions, reccommendations or itineraries would be welcomed.

    Thank you,

    • elena nacci ha detto:

      Hi Randy,
      Thanks a lot for contacting me.
      The area of San Gimignano is very scenic and very strategic to visit Tuscany. First of all, take a look at my suggested day trips to make from San Gimignano.
      As for an itinerary, I would suggest you start your day early visiting Monteriggioni, passing from Siena, and then reaching Montalcino and the Abbey of Sant’Antimo. At this stage you’ve reached the scenic Val d’Orcia area, where I would pass the overnight so to have time to visit Pienza, Montepulciano and Cortona before heading back to San Gimignano again.

      I remain at your disposal for any further suggestion,
      have a nice day,

  • Corinne ha detto:

    Hi Elena

    We are considering flying from the UK next June (2016) to Pisa for 2-3 weeks, we wanted to have a number of days staying and exploring Tuscany and also drive down visiting the Amalfi coast, arriving in Naples to fly home to the UK.

    Do you have any suggestions for routes or places to stay and typically how low is required in the different areas.

    We visited Venice earlier this year and spent 5 days there, anything less and I would have felt cheated that we hadn’t seen it all.

    Kind Regards


    • elena nacci ha detto:

      Hello Corinne,
      Thanks a lot for your message.

      You’re so right about Venice! What a unique place 🙂

      In 2-3 weeks you’ll be able to see a lot of Italy and Tuscany. You may stay in Tuscany for 1 week and explore its main and most beautiful sights. This one week itinerary of Tuscany can be of help. You may stay in one possibly 2 different places in the region, one maybe in San Gimignano or Chianti, and the second maybe in the splendid countryside of the Val d’Orcia Park south of Siena. Moving south towards the Amalfi Coast you can have the opportunity to visit incredible sights, like Pitigliano, Sorano, Sovana, Orvieto, and Civita di Bagnoregio.

      Moving further down towards Naples, I suggest you visit the wonderful Reggia di Caserta. The Amalfi Coast is stunning and incredibly full of fantastic places to stay, for suggestions on where to sleep just let know,

      For places to stay in Tuscany you may start by having a look at the accommodations I recommend on the blog, and for any further tip, just ask.
      Have a nice weekend,

  • Lee ha detto:

    Hi Elena,

    My husband and I will be visiting Italy in May 2016 for 15 days. We plan to stay 5 days in Rome, 6 days in Tuscany and Florence, 3 days in Venice and 1 day in Milan.
    I am thinking of following your itinerary on the drive from Rome to Florence. I have allocated 3 days to do this drive so that we could stop by the interesting and beautiful places. Thereafter, we will drive to Florence and stay there for 3 nights. we will be renting a car for 3 days from Rome and return in Florence at the evening of day 3. after visiting Florence for 2 days, we would like to visit Lucca and Pisa by train on our last day in Florence.
    Could you please advise us whether this is a good arrangement for our Tuscany & Florence trip. Should we drive from Siena to Pisa and Lucca instead of going to Florence then catch a train there.
    Please advise us a good place to choose as a base for our driving trip in Tuscany.
    Where will be a good place to rent a car in Rome, should we rent it from the city centre as I am concerned about driving into ZTL zone.
    This is our first trip to Italy, appreciate your help and suggestions.

    Best regards,

    • elena nacci ha detto:

      Hi Lee,
      thanks for your message.
      I’m happy you have decided to follow my itinerary on the drive from Rome to Florence, great choice:-) You mean the road map on this article or this road trip from Rome to Florence, that is more detailed and also includes amazing sights like Orvieto and Civita di Bagnoregio. Take a look and let me know. In case, a great place to stay during your driving trip is the scenic natural countryside of the Val d’Orcia with its many beautiful hill towns. Here are some accommodations ideas in the area.

      Your plan is really very good! 3 days for the drive, then Florence, and from there Lucca and Pisa by train on a day trip.
      It’s better to reach Pisa and Lucca by train from Florence, both cities has centrally located train stations.

      A good place to rent a car in Rome would be directly at the airport, like Fiumicino, as it is right close the motorway.

      Please do not hesitate to ask any other question,
      Have a nice day,

  • Sue ha detto:

    Hi Elena,

    What a fab blog. I love it!

    My sister and I are planning a mini road trip through Tuscany. We’re arriving on 3rd October in the evening in Pisa and flying out from Pisa on 7th October in the evening. I’m not sure if we have the time to do everything on our list and was hoping that you could help.

    Our route is currently mapped out as follows:
    – Leaning Tower of Pisa
    – Volterra
    – Cortona
    – Rome
    – Naples
    – Positano

    We then drive back up to Pisa for our flight back on the 7th. My sister wishes to see Florence if there’s time. But I’m not too sure. Do you think this route is doable in the time that we have? And where do you think we should stop and spend the night along this route (I have yet to book our accommodations)? We’ve always wanted to see Positano, hence the reason that it’s our final destination before looping back towards Pisa. Your insights are very much appreciated.
    Thanks in advance, Elena.


    • elena nacci ha detto:

      Hi Sue,
      I’m so happy you like my blog 🙂
      So you have 4 full days or a bit less for your plan. I honestly think your route is too full of things to see. Consider that the jorney from Pisa to Positano takes about 6 hours and half with no stops on the way. This way you’ll spend of your time traveling.
      You have 2 possibilities; taking a plane from Pisa to Naples to visit Positano and the Amalfi Coast, or skip something for this trip to Italy.
      You may visit Tuscany and Florence more calmly and reach Rome by car but skipping Positano. Or visit Positano by plane, skip Rome, and spend the rest by visiting the fantastic attractions of Tuscany.

      Get back to me for any further suggestion,
      elena from Florence

  • Nondas ha detto:

    Hello Elena,
    We are visiting Italy for 15 days (14nights) arrining in Milano and departing from Rome.
    We will rent a car and want to do both routes you mention on the article.
    We are planning to spend a couple of days in Milan and then head to Florence, visiting 5 terre on our way.
    Any ideas for the way between Milan and Florence, is it nicer to go from Genova area or Parma?
    After 5 terre we will head to Pisa and then Florence, is Pisa worth spending a night?
    Also we have visited on the past Roma so we are not planning to stay att all, just head to Ciampino airport.

    • elena nacci ha detto:

      Hello Nondas,
      I’m glad to hear you’re going to follow my suggested road trips through Tuscany, as they cover much of the best Tuscan sights. This further road trip from Rome to Tuscany and back can also be of your interest.

      As for the way between Milan and Florence, of course it is nicer to go from Genova area and the Cinque Terre. I would spend half a day in Pisa, mainly visiting the wonderful Piazza dei Miracoli and the Tower.
      Let me know if you need any more help,

      • Nondas ha detto:

        Hello again! Can you take a look at my girlfriend’s itinerary?

        You think that we should spend more nights in one place and have it as a base for day trips than spending every night in another town?
        If so which ones would be the more convenient ?

        Thanks again, the itinerary is as follows.

        Tuscany Itinerary suggestion
        Day 1. 5/11 Arrival Milan
        Sightseeing and Overnight

        Day 2. 6/11 Milan Bergamo. Pick up car.
        Bergamo Cinque Terre Manarola. Approx. 4hours

        Day 3. 7/11 Cinque Terre.

        Day 4. 8/11 Manarola Castelnuovo di Carfagnana (95km 2h30min)
        Castelnuovo di Carfagnana Lucca (48km 1h)
        Overnight Lucca

        Day 5. 9/11 Lucca Pisa (30min). Sightseeing.
        Pisa San Miniato (48km/1hour)

        Day 6. 10/11 San Miniato – San Gimigiano (40km/1hour), via Voltera 81km/2hours

        Day 7 11/11 San Gimigiano Florence (61km 1h36min)
        Overnight Florence

        Day 8. 12/11 Florence.
        Sightseeing. Overnight Florence

        Day 9 13/11 Florence drive through Chianti region. Greve in Chianti, Radda in Chianti, Gaiole in Chianti, Castellina in Chianti, 76km/2h15min

        Day 10. 14/11 Chianti region – Sienna
        Overnight Sienna

        Day 11. 15/11 Sienna
        Sightseeing and overnight

        Day 12. 16/11 Sienna – San Quirico d’Orcia, Pienze, Montepulciano (69km/ 1h 30min)
        Overnight Montepulciano

        Day 13. 17/11 Montepulciano Castiglini D Orcia Pitigliano (91km/2h30)
        Overnight Pitigliano

        Day 14. 18/11 Pitigliano Bagnoregio (43km/1hour)
        Overnight Bagnoregio

        Day 15, 19/11 Bagnoregio Rome (2h30mi)

        • elena nacci ha detto:

          Hi Nondas,
          Sorry for the delay!
          Your itinerary id good and absolutely doable. Being quite full of beautiful sights to see, I would not add any more destinations/stops.
          Of course you’re sleeping almost every night in a different place, so you may consider spending more nights in San Gimignano and make these day trips including Chianti.
          I remain at your disposal,
          Have a nice day,

  • Tolga (Mr.) ha detto:

    I need your kind suggestions about the trip to Tuscany territory. We will be in Italy betwren dates 22.09.2015 to 28.09.2015. We will be back to Turkey from Rome.
    We have seen Rome, Florence & Venice before. Now we would like to see different places in Tuscany and our tour would be for historic places, to joşn to the local residents, eat traditional foods and drink wines. Now I urgently need your reccommendarions for;
    1) Do you agree if we start this trip from Genova and finish in Rome?
    2) Do we have to rent a car or we can manage this trip with public transports?
    3) Where we should stop for the accommodation, as a cheapest way?
    4) Can we follow your comments which had mentioned on your articles or any alternatives that you can suggest?

    Please I urgently need your kind reply

    In advance thanks dor your kind assitance

    Look forward to hearing from you soon

    Kindest Regards

    • elena nacci ha detto:

      Hi Tolga,
      Thanks for your message! Hope my answer is not coming too late.

      >1) Do you agree if we start this trip from Genova and finish in Rome?
      Yes, do you intend to visit the Cinque Terre also?

      >2) Do we have to rent a car or we can manage this trip with public transports?
      For Tuscany a car is always recommended, from Genova to Pisa you can take a train and then rent your car once in Pisa and start explore the region.

      >3) Where we should stop for the accommodation, as a cheapest way?
      You can find a lot of good and cheap accommodations also on your way, look for B&Bs. Any idea where in Tuscany? So I can send some suggestions.

      >4) Can we follow your comments which had mentioned on your articles or any alternatives that you can suggest?
      Of course you can follow my comments. For any other specific question, just ask.

      I remain at your disposal,

  • Barbara ha detto:

    Hi Elena,
    I am traveling to Italy October 10-25. Itinerary includes 4 days in Rome. 3 days in Naples. Taking the train from Naples to Florence. Picking up rental car then driving from Florence to a cottage right outside Siena, where I will be in Siena for 4 days, others in my group are lucky to have another week in Tuscany. We are a little nervous about driving. Should we have any concerns about driving around Tuscany ? Any suggestions on top winery around Siena ? I don’t want to miss anything I “shouldn’t ” miss while in Tuscany so any insight would be helpful I am ending my trip with 3 days in Venice. Thank you !

    • elena nacci ha detto:

      Hi Barbara,
      thanks for your message.
      Your itinerary is good!
      While in Naples, do not miss a tour of the wonderful Amalfi Coast!
      You should not have any concerns about driving in Tuscany. Once you’ve left Florence, the drive into the countryside or any other hill town, will be a pleasure.
      Here are some for driving in Tuscany. As for top wineries around Siena, I can recommend Poggio Grande and Ciacci Piccolomini. Others tips here.
      Siena is perfect to explore Tuscany and its many sights. This is a list of the best day trips to make from Siena.
      Let me know if you have other questions,
      Have a nice stay,

  • Tawna ha detto:

    Ciao Elena,

    Not sure if you will get this message in time. We are in Cortona, and will be driving to Montisi (Siena) on Sunday…. we would like to go on a scenic route vs. highway…. we are making use of a GPS, don’t have an old fashioned map at this point. Just wondering if you could share with us some tips or names of towns or roads that we can enter into the GPS to follow, which would take us to scenic places, photo opps, etc.

    Also, while we are in Montisi (near Sinalunga, Buenconvento, etc) we will have about 6 days to drive around (I’ve been there before, but without a car… and now we have a car, so I want to go find the gems!!)


    Grazie mille,


    • elena nacci ha detto:

      Dear Tawna,
      I’m so sorry for my late reply.
      Please tell me if you might still need some suggestions,
      Have a nice day,

  • Cristina ha detto:

    Hello!! I love your blogg. Congratulations. Incan really see your passion for writting and the love you have for Italy. It is really nice funding that! I felt in love with Italy right after I saw “Under the Tuscan Sun” movie!!!

    I am planning a trip to Italy with my husband for our 1 year annyversary next summer. We are a young couple (25-28 years old). We are going to rent a car and make a road trip! And we have 15 days!!

    We have only been in Rome/Florence in a Cruise ship basis.

    We want to see everything (Rome, Florence, Milan, Venice, Amalfi Coast, Tuscany) but unfortunately there is not enough time!

    What do you recommend we do? What would you visit each day and in which cities/towns would you sleep each Day?

    Thank you again for your time and enthusiasm! I really appreciate it

    • elena nacci ha detto:

      Hi Cristina,
      Many thanks for your nice message! I’m very happy you like my blog 🙂

      “Under the Tuscan Sun” is a lovely movie, I saw it again the other day!
      So you have 15 days to see the best of Italy, let’s see how to plan your time at its best. You can start your trip either from Rome or Venice depending on where you’re arriving.
      In case you’re arriving in Rome, you can spend there 2 days, then I would move south to reach the enchanting Amalfi Coast. You might rent a car in Rome and reach Amalfi where I would stay 3 days. Then come back towards Rome but continue for Tuscany, maybe following this interesting itinerary that takes you though some fantastic Italian destinations, including Orvieto and Civita di Bagnoregio. Your next base can be south of Siena, amid the dreaming countryside of the Val d’Orcia; Pienza and Montepulciano are great to stay; you could stay there 3 days. Here are some ideas on how to spend 2 weeks across Tuscany best sights.

      Go north and dedicate a full day visiting the marvelous Siena, then make San Gimignano or Chianti your next base for other 2 or 3 days. After reach Florence, where, if you wish, you may spend 1 night or 2. Leave your car in Florence and reach Venice by a fast train; I would spend in Venice the remaining of your holiday.

      You can find some more ideas for your Italian tour reading through this article about the best tour of Italy.
      Do not hesitate to contact me again,

  • Jeff Reeves ha detto:

    Elena, thank you posting this valuable info. Next Saturday my wife and a few friends need to travel from Rome to Lucca. They plan to leave a hotel near FCO around 7:00 a.m and need to be in Lucca at 4 pm. I was trying to find the most scenic route for them to travel, and the Via Cassia seems to be a must as part of that journey. They may have time to stop in just two places along the route. What two stops would you recommend the most along that route?

    • elena nacci ha detto:

      Dear Jeff,
      I’m very sorry for my late reply.
      Which route did you take? How about your holiday?

      For any other info do not hesitate to contact me again,
      Have a nice day,

  • Suzanne ha detto:

    My husband and I are planning a 3 week trip to Italy in May 2017. Looking at Rome, Venice, Tuscany, Siena, San Gimignano, Lucca, and Florence. Would like time to see beautiful countryside, meet locals, eat eat and eat wonderful Italian food. Probably take train for some sections, drive, and hopefully moderate easy walking as we are Seniors. We can rent a car at 76yrs old correct?

    Any help would be greatly appreciated. Looking at a trip for a long time and this is our first trip. Places to stay, cooking lessons, any input appreciated greatly.

    Thanks very much

    • elena nacci ha detto:

      Hi Suzi,
      Many thanks for contacting me. I’m happy to give some suggestions for your first trips to Italy. You may start by having a look at this itinerary of Italy that I usually suggest. In 3 weeks you will have time to admire the best Italian sights and relax at the same time.
      Tuscany is actually the right place for relaxation thanks to its unique countryside, vast views, wonderful food and wine… and an endless number of other things.
      Of course you can rent a car 🙂 Train is useful when moving to reach Venice and Rome to and from Florence. When staying in Florence’s center you’ll not need the car as you can use public transportation to move around. For Tuscany you may start by reading this post about planning the ideal trip. For places to stay in Tuscany I particularly love Villa Bordoni in Chianti that also offers great cooking lessons, and Farmhouse il Rigo near Pienza in Val d’Orcia, also offering cooking lessons. For other accommodations take a look through the blog:-)

      Start having a look and get back to me for any further help,
      Have a nice day,

  • Shantala ha detto:

    Hi in italy with 2 of my friends and instead of taking the conducted tour of pisa and Chianti on one day and the train the next day to Rome, i would like to do a road trip to these places. What would be the cheaper and better plan? Road trip or the conducted tours $135 per person for pisa and Chianti and then train the next day to Rome?Our 2 night stay in florance and two nights in Rome are already booked. Would you know how much it costs to hire a car for 2 days?
    Thank you so much

    • elena nacci ha detto:

      Hi Shantala,
      Thanks for your message.

      You can also do your day trips on your own.
      Are you staying first in Florence? while in Florence you can take a fast train to Pisa while rent a car to explore Chianti and the Tuscan countryside. If you like driving you may also reach Rome from Florence by car on this scenic itinerary on the road.

      On this website you can check the price to hire a car for 2 days, that is approximately 40 US $.

      Do not hesitate to contact me again,
      elena from Florence

  • Citra Andries ha detto:

    Dear Elena,
    Your website is awesome! Can’t thank u enough for information you share.
    But I have questions. I plan to visit Tuscany around 19 – 22 Feb, my plan is driving from Rome to maybe Siena. I plan to drive because I want to witnessing my self the famous beauty of Tuscany landscape. My questions are:
    Which city I should visit?
    Is it snowy around the city that I might visit?
    Is the view still beautiful? or it all will look flat and just white?

    Grazie 🙂

    • Citra Andries ha detto:

      Hi Elena,

      I read your recommendation here and here
      So the my questions now are
      1.Is it snowy around the city that I might visit?
      2. Are those city still have beautiful view like you mention even on February? My priority is to enjoy the view, taking pictures.. so if the wine area are close, it’s okay for me.
      3. This is my first time visit Italy, first time driving in euro zone, is it safe to driving on February?

      Thank you again, Elena 🙂

    • elena nacci ha detto:

      Hi Citra,
      Thanks for your messages!
      The Tuscan landscape is beautiful also in February 🙂 Driving from Rome to Siena is a good idea, also take a look at this other road trip I recommend. Siena is incredibly beautiful, take the time to visit it carefully. If you’re staying in or near Siena you can make a lot of fantastic day trips, including Monteriggioni and San Gimignano, splendid medieval hill towns.
      Usually February is not snowy, and driving during this time of the year is absolutely safe.
      For any further question just get back,
      Have a nice day,
      elena from Florence

  • Jimmy Ng ha detto:

    Hi Elena
    Thank you so much for the info. It has been very useful in planning our trips in Tuscany. My friends and I will be driving from Florence to Siena and intend to do the Via Chiantigiana route as you suggested. One question I have is the vineyards that you would recommend that we could possibly visit for wine tasting and lunch.

    We will spend overnight in Siena and will then proceed to Pisa through San Gimignano the next morning. Do you have a suggested route that we could take, the vine yards that we could visit?

    Thanks very much in advance.

    Cheers, Jimmy

    • elena nacci ha detto:

      Sorry for answering you only now!
      In case you still need my help, get back, on the contrary, you’re welcome to tell about your Italian trip!

  • Nora ha detto:

    Elena: LOVE your website, thank you so much! My husband & I plan to fly into Florence and out of Milan. The amount of time we will allow is flexible 1-2 weeks. This is why your advice is needed. We have already visited the city of Florence and do not want to spend additional time there. We would like to position ourselves at one location and do day trips. We are not interested in museums, big cities or churches but would rather enjoy small town villages, scenic country roads, wineries, and medieval towns. We are good with popular destinations as well as ‘off the beaten path’. We are most interested in seeing how the locals live, culinary tradition & products, wine & cheese & some shopping. We have been to San Gimignano and loved it! We would like to go back to San Gimignano and also visit Sorano, Pienza, Montalcino, Chianti, Montepluciano, Val d’Orcia and Valdichiana. Where can we position ourselves for our day trips? How much and what in each day is doable? After visiting the Tuscany region we plan to go to Cinque Terre. Do you have a route suggestion with stops? Any recommendation on time needed for our plan? Also, do you suggest wineries for tasting? Do we need to make reservations for tastings? A wine & cheese pairing and a pizza making class would be of interest to us as well. Thank you so much for your assistance! Our visit will be late October 2017, prior to a cruise from Barcelona to the USA. Nora

    • elena nacci ha detto:

      Dear Nora,
      I’m so sorry for my late reply, I’m back after a long pause!
      How was your trip to Italy? You’re welcome to tell about it 🙂

  • Joana Soares ha detto:

    Hello Elena! Thank you for sharing your amazing roadtrips with all of us! I was wondering if you find it possible to do both of them (starting in rome and finishing in Firenze) in just 3 days, visisting all the places you mentioned. Or should I skip some? Thank you 🙂

    • elena nacci ha detto:

      Ciao Joana! thanks a lot for coming here! I’m happy you like my road tips for Tuscany 🙂
      It’s actually doable, though I would skip some stops/villages on your way; this also to make you appreciate these fantastic destinations better. And you may also consider an overnight in between Rome and Florence, in Val d’Orcia or in Siena itself. On your way from Rome to Siena via the Cassia road I wouldn’t miss Bagno Vignoni, Montalcino, and Pienza, while on your way from Siena to Florence don’t miss Castellina, Greve and Gaiole in Chianti, and maybe have some wine tasting at some scenic castela like the Castle of Verrazzano or the Castle of Brolio. Some other tips you may find interesting are in this post about a road map from Rome to Tuscany and back 🙂

      For any other suggestion, I’m here 🙂

  • robyn mullenger ha detto:

    Hi Elana

    We are two over 60’s friends coming to Italy for two weeks in late June 2019. I have booked 4 nights in Rome at the beginning and 4 nights in Venice at the end. With those two cities in mind, I think we will need more of a relaxing pace for 6 days in the middle.
    I have been to Lucca once and loved it. Until I read your blog above I had thought we could stay in Florence and do day trips out to a winery and then spend 3 nights in Cinque Terre.
    But you inspire us to hire a car and stay in the countryside, old farmhouse with a pool or similar and see
    Val d’Orcia and Siena.
    What would you suggest?
    I look forward to hearing from you
    Kind regards

  • Demet ha detto:

    Dear Elana,

    We are planning a second time trip to Tuscany this May. This time we will also making a day trip to Montepulciano, Val D’orcia , Montacino area driving from Arezzo area. Could you recommend me the best route involving lunch and/or early dinner?

    Thank you very much,

  • Angela Gomez ha detto:

    Ciao Bella!

    My fiancé and I are planning 3 days and 2 nights at Monticchiello. After our wedding on the 1st of june 2020 to the 3rd of June. Then proceed to Venice afterwards. Can you suggest an itinerary for us? Florence and rome not included.

    Grazie Mille!


    • elena nacci ha detto:

      Ciao Angela 🙂 ❤️
      Wedding in Tuscany? Wonderful!
      Monticchiello is lovely, so, a tour of the best sights of the Val d’Orcia is recommended, mybe also including Montepulciano and Cortona. Then, you may continue with a visit to the Chianti area south of Florence, and a visit to the wonderful and fascinating hill towns of San Gimignano and Volterra would be great!
      I’m here if you need any more suggestions 🙂

  • Adrinna ha detto:

    Hi Elene,

    We will be traveling to Tuscany/Florence from with 2 kids ages 6 & 10 Rome April10th-14th and taking the train to Venice We want to rent a car. Trying to decide where to stay in Tuscany and we wanted to spend the last day in Florence. It’s Holy Week and just saw that the Museums are closed on Mondays. Would it be better to take a train and start there on the 10th? We want to visit Orvieto, Civita di Bagnoregio, Pitigliano, Thermes de Saturnia, Montepulciano, Siena, Pienza, San Gimignano. Any recommendation on where to stay and best to travel to these towns.

  • Terry ha detto:

    My wife and I wanted to do a driving trip by ourselves through Tuscany. We would to get a route designed that would allow us to explore all the small country side towns. We would like to eat at smaller home style restaurants in the different towns while exploring the countryside.
    We would have 2-3 weeks.

    Can you advise if you or anyone could provide a route and map with suggestions.

    Terry Yates

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