Tuscany Holiday Plan: An Itinerary to Discover the Best Sights in Tuscany in two Weeks, Italy

A Two Weeks Itinerary in Tuscany

Last Updated on Sunday 19th, January 2014 / 14:08 Written by
  • A Two Weeks Itinerary in Tuscany
  • A Two Weeks Itinerary in Tuscany
  • A Two Weeks Itinerary in Tuscany
  • A Two Weeks Itinerary in Tuscany
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Have you ever been to Tuscany? If not, you’ll find it is an amazing country:-) There are a lot of good reasons to visit Tuscany and pass a great holiday!

Are you going to stay in Tuscany for more than just a few days? You are in the right place!

As some American friends have been asking me how to plan a two weeks vacation in Tuscany, here is the travel itinerary I suggest to explore Tuscany’s amazing and exceptional sights at its best. Two weeks is actually the right time to get the most out of this beautiful region of Italy.

Renting a car or not?

A car is definitely required, at least after you’re leaving Florence, considering the secluded location of many of the smaller suggestive villages, that cannot be reached by public transportation but are all waiting for you to be explored.

As you are going to travel by car, you may well stay in some nice and peaceful hilltop villages amid the scenic Tuscan countryside for most of your stay.

On the contrary, if you are not going to rent a car at all, base yourself in Florence, that is well served by public transportation, having a central location in Tuscany. If that’s the case, here are the Best Day Trips from Florence.

Let’s start with our itinerary! Spend the first 3 days in Florence, as you will probably be flying from abroad to Florence or Pisa airports, and then move to 2 different hill towns and use them as your base.

Two weeks in Tuscany Itinerary

1. Three Days in Florence beautiful historic center

Ponte Vecchio in Florence

For the first three days of your holiday, I’d suggest you stay right in Florence’s historic center, so to visit and appreciate as many attractions as possible. Florence is the cradle of the Renaissance, the city of art at its highest levels, the city of the David by Michelangelo, the city of Dante Alighieri…and nowadays also the perfect place for a great shopping :-)

From the Uffizi and the Ponte Vecchio to the church of Santa Maria Novella, the Cupola del Brunelleschi and Palazzo Pitti, Florence retains so many unexpected treasures and such impressive sights, that one lifetime wouldn’t be enough to visit all it has to offer.

Where to stay in Florence:

There’s a full article dedicated to the Top Attractions to visit in Florence, and one with my personal recommendations about Florence Best Hotels and Charming Accommodations. Hotel Brunelleschi is particularly amazing, being also a museum!

Pisa and Lucca

Staying 3 nights will give you the possibility to get the best of Florence, and since you are there, do visit Lucca and Pisa on a day trip from Florence using the train. There are in fact fast trains running from Florence to Pisa in just one hour. Florence Santa Maria Novella train station is in the town center so it’s very convenient. You can find train timetables at www.trenitalia.com.

Pisa is a must visit and not just for its famous Leaning Tower! All the Square of the Miracles is a unique incredible work of art! Lucca with its impressive circle of walls, a fantastic round square that is an ancient Roman theatre, the wonderful churches and the many charming shops, cannot miss from your itinerary as well.

Tips on moving around Florence’s center

Once in Florence you can conveniently explore the town also on foot, as the historic center is quite small, and all the main sights are walking distance. A good alternative is to move around by bus. ATAF is the public bus company in Florence. For more information about bus routes, tickets’ fares and much more, visit ATAF official website.

Renting a car once in Florence

While in Florence do use public transportation to get around and not the car, there’s a lot of traffic, driving can be quite stressing and there is little and expensive parking. Once you are leaving Florence to explore other parts of Tuscany pick up your car at your rental company in town.

Cars can be picked up at Florence airport (in this case you can take the car directly at the airport and spend in Florence not the first but the last 3 days of your trip) , or in Florence downtown, near the Santa Maria Novella train station. You can rent your car online here.

2. San Gimignano as a base for your holiday

The Devil's Tower in San Gimignano

After you have visited Florence, pick up your car and start to explore the beautiful countryside driving up and down Tuscan hills, until you get to San Gimignano, wonderful hill town famous for its scenic 14 medieval Towers, where you could stay 5 or 6 days. San Gimignano itself has much to offer, here you can read about all of San Gimignano’s Top Attractions I suggest to visit, from the beautiful paintings at the Museo Civico, to the stunning panorama from the Torre Grossa, to the Torture Museum and the stunning frescoes in the Duomo.

From San Gimignano you can then start to make fantastic day trips:

  • Chianti, charming countryside, green hills and vineyards, known worldwide for its fine Chianti Classico wine and its lovely hill towns, like Castellina in Chianti. Having the car here is great! Enjoy driving through Chianti panoramic and winding routes.
  • Volterra, beautiful Etruscan town enjoying a stunning hill-top location on a spur of tuff in perfect isolation, here you can admire the exceptional remains of its Roman theatre, wander its characteristic alleys and visit the stunning Etruscan museum.

Where to stay in San Gimignano:

I recommend the B&B Locanda Viani, right outside the city walls with a stunning view over the towers, or, if you prefer to stay right within the town’s walls, choose Hotel Antico Pozzo, elegant 3 star hotel.

Where to park in San Gimignano:

As you are traveling with your own car, it can be useful to now where to park in San Gimignano. The historic center of San Gimignano, that is enclosed within the walls, is a limited traffic area, so the hotel you’re going to choose will have to give you special permission to get in front of it to load and unload your luggage. In the case of Hotel Antico Pozzo the car park is number 3, have a look here. While, if you are staying stay at Locanda Viani, just outside the city center, you will have the parking in front of your accommodation.

There are 3 main public car parks in San Gimignano, here you can have more detailed info about Parking in San Gimignano.

3. Two or Three days in Siena, not just the city of the Palio

Before heading on to Montepulciano, you may also spend 2 or 3 days in Siena, so to have the right time to visit most of Siena’s incredible sights. Staying in Siena’s historic center is an experience! Also thanks to its hill top location amid a stunning natural landscape, Siena is probably the most beautiful major art town in Tuscany, literally!

From the amazing shell shaped Piazza del Campo with the imposing Torre del Mangia, passing through the wonders of the Duomo, like the Piccolomini Library and the frescoes by Pinturucchio, arriving to the interesting Museum at Santa Maria della Scala. While staying in the very heart of the historic center, you will have the possibility to admire Siena Top Sights and Attractions. Just outside Siena is Monteriggioni, medieval town with a perfect circle of walls all enclosing its suggestive tiny center.

You can find a post with useful suggestions on the Best Day Trips from Siena

Where to Stay in Siena

I recommend staying at the lovely Relais Campo Regio, right in the town’s center and with fantastic views over the Duomo. It is an elegant hotel with beautiful bedrooms, some with frescoes, and all the main monuments and sights of Siena are all reachable on foot. You can find also further suggestions on Siena Luxury Accommodations here.

Where to Park in Siena:

Siena is again a limited traffic area, you will find that each hotel usually has a garage near it. Any hotel you’re going to book, however, will give you all detailed info on how to reach them, a permission if required, and will guide you to the nearest car park. Find more info about Parking in Siena.

4. Montepulciano as a base to explore southern Tuscany

Montepulciano, hill town in Tuscany near Siena

For the last part of your trip I suggest staying south of Siena, in the area known as the Val d’Orcia, magical countryside region and natural park with the most scenic and surprising landscape in Tuscany! That’s where come all of those beautiful postcards you see of the evocative Tuscan countryside :-)

Use Montepulciano, one of the most beautiful towns of all of Italy, as your base. I suggest you spend here most of your stay, 4 or 5 nights. Located between the Valdorcia and the Valdichina, this impressive hill town is of rare beauty and is perfect to explore that extraordinary part of Tuscany. From Montepulciano, you can make a lot of fantastic day trips to some of the most beautiful sights of southern Tuscany:

  • Pienza and Monticchiello: Pienza is not just an exceptional Renaissance village that was built in just 3 years for the want of Pope Pius II, but it’s also the town of the tasty pecorino cheese. Pienza is also one of the most romantic places in Tuscany. On a panoramic hill overlooking Pienza, rises Monticchiello, tiny village with thick walls that retains a suggestive atmosphere.

  • Montalcino is an impressive town atop a hill, famous for its Brunello wine. It is dominated by a majestic and panoramic fortress with bastions, wander throug its characteristic alleys and enjoy some shopping :-)

  • The Abbey of Sant’Antimo near Montalcino, that you can visit in combination with Montalcino, is a mystic and incredibly suggestive place, don’t miss it!

  • Bagno Vignoni, peculiar hamlet with ancient thermal springs, having a large ancient Renaissance pool as its main incredible square!

  • Rocca d’Orcia: climb up its tower to enjoy a breathtaking panorama all over the Orcia Valley.

  • Crete Senesi: driving northeast of Montepulciano you’ll find yourself immersed in the heart of the Crete, one of the most impressive and peculiar landscape of Tuscany for their lunar and almost deserted landscape

  • Arezzo and Cortona: Arezzo is extremely beautiful! Visit the outstanding frescoes by Piero della Francesca in the Basilica of Saint Francis, the enchanting Piazza Grande with beautiful loggias by Giorgio Vasari, and much more. In Piazza Grande Roberto Benigni also shot some scenes of La Vita è Bella. Cortona, on the very top of a hill overlooking one of the vastest panorama in all of Tuscany, is all to discover, with a stunning Etruscan museum and lovely shops.

  • Radicofani: Located at the far end of the Val d’Orcia, Radicofani is a charming village dominated by an imposing fortified fortress, again boasting an incomparable panorama over an impressive landscapes with ravines and hills running one after the other.

  • Pitigliano: As you are in Tuscany for 2 weeks, I highly recommend you visit Pitigliano, about one hour and 20 minutes from Montepulciano. That’s one of the most spectacular and peculiar town in Italy, rising right out from the rocks! Next to Pitigliano, also take the chance to visit the small and incredibly characteristic villages of Sorano and Sovana, their atmosphere is really suspended in time, time here seems to have stopped. In Sovana you can also admire an ancient treasure of gold coins, that was accidentally discovered here in recent years!

Many of the hill towns and attractions of the Val d’Orcia can be visited also in one day, say, you could visit Pienza, Monticchiello and Bagno Vignoni in one day. Here you can find my list of the Top Ten Attractions to visit in Val d’ Orcia.

Where to stay in Montepulciano:

I recommend Osteria del Borgo Apartments, offering lovely apartments in typical Tuscan style with an amazing view. Just note, however, that to reach the apartments you will have to make a lot of stairs, as there’s no lift. Another very good and chic alternative could be La Locanda di San Francesco, an exclusive retreat with luxury rooms and amazing view over the Tuscan countryside.

Tuscany Holiday Plan

Planning your holiday in Tuscany? If you need help in arranging your trip or if you have questions as to the best travel itinerary, just ask a question here! I’ll be happy to help!

See Also:

Tuscany Itinerary 7 Days

About the author

Hi! My name is Elena, I'm a travel writer and a happy mom living near Florence. I love to explore Tuscany to discover special places and I have a great passion for Tuscan Cooking. On this blog I share my experiences on special hotels and places to visit in Tuscany and Italy, and about my grandmother's tasty Recipes! I'm happy to help travelers plan their holiday in Tuscany :-)

View all articles by elena nacci

27 Comments on “A Two Weeks Itinerary in Tuscany

  • HI My husband and I are thinking to explore Tuscany in August starting from the 8/9th August returning around 22/23 August. We would fly to Rome so we would need to catch a train to go to Florence. I was thinking to spend some days there and then move on, renting a car. I am presently studying to get the Wines and Spirits Certification so either staying or visiting wineries is a must. Coming back would like to spend a day in Viterbo where I would be visiting friends before catching the flight back home. Would appreciate if you could give me some hints on an itinerary whereby I can explore Tuscany as well as some recommendations on accomodations. I always prefer the Agriturismo type. Thanks Stefania

    Reply
    • elena nacci Post author

      Dear Stefania, here I am :-) thanks for getting in touch! Renting a car is the best way to explore Tuscany! After the days spent in Florence, I’d soon move south to reach the Chianti area, one of the best areas to be for visiting wineries and beautiful cellars. Among my favorite wineries in Chianti I recommend the scenic Badia a Coltibuono in Chianti, that also has a great restaurant, and the beautiful Badia a Passignano, an amazing place, not to mention the wine and the osteria! Chianti is literally full of special accommodations to stay, have a look at my selection of lodgings in Chianti and get back for further suggestions. Once you’ve left the Chianti region head on in direction of Siena, where I’d spent a whole day in its beautiful and unique historical center, simply magical! Go south of Siena to explore the Crete Senesi and then the suggestive landscape of the Val D’Orcia Natural Park, where wine is absolute protagonist. The Orcia Valley is home to some of the most appreciated wines in the world: Nobile of Montepulciano and Brunello of Montalcino. The hill towns of the Valdorcia are all stunning! Here is my selection of special places to stay in Valdorcia. Among the many wineries there, I suggest Ciacci Piccolomini, a renowned farm with beautiful vineyards and 3 ancient wine cellars in Montalcino. We are in the area where the most precious wine of Tuscany is produced, the Brunello of Montalcino. There’s also a beautiful panoramic terrace where you can taste wine. Chianti aand Valdorcia are the best wine producing areas of Tuscany and also amongst the most intriguing parts of Tuscany. As you’ll be back to Rome with the car, I suppose, you may get some ideas from this itinerary I recommend on the route from Rome to Tuscany and back. Finally you may also consider a stop to visit the wonderful Città del Tufo; Pitigliano in particular. Do contact me again for any other help needed! Enjoy planning your trip to Tuscany :-)

      Reply
  • Hello Elena,

    Love your site! We are starting to plan a trip in September. Thinking of flying into Milan & taking a train to Florence.
    Arriving on a Wednesday and staying three nights. Renting a car on Saturday and driving to Tuscany.Would like to rent a Villa for a week and do day trips using the Villa as our base. The following Saturday, drive to Vienna or take a train and stay for three nights. Leave for the airport on Wednesday, or stay one night in Milan the night before departure. This would give us two weeks. If you have any suggestions for other alternatives, and areas to rent a Villa for easy access for day trips would be appreciated.

    Thank-you from the Windy City.
    Kathleen Tuffner

    Reply
    • elena nacci Post author

      Hi Kathleen,
      I’m happy you love my site :-) Oh the Windy City! it’s so beautiful! I’d like to come one day :-)
      So you’re staying in Florence for 3 nights, great! Florence is such a spectacular town! It is one of those incredible cities that must be visited at least once in a lifetime: the masterpieces at the Gallery of Uffizi (Leonardo da Vinci, Michelangelo, Botticelli), the countless art museums, the wonderful churches with frescoes, the famous and mysterious Cupola del Brunelleschi, and the Ponte Vecchio, the fashion shops…Florence’s attractions are really a lot. You can find useful tips on Florence and its surroundings in this blog post dedicated to using Florence as a base in Tuscany.
      Coming to the areas where to rent a Villa, I’d choose between the Chianti or the Val d’Orcia.
      Chianti enjoys a strategic location between Florence and Siena, while the Val d’Orcia is the wonderful area south of Tuscany, famous for its stunning landscape. The Best Place to Stay as a Base in Tuscany: Chianti, Valdorcia, or both? is an article on the blog that can help you decide on the location that best suits your needs! Both areas are beautiful and can be great for fantastic day trips, the Val d’Orcia allows to visit more also of the southern part of Tuscany and of many lesser known gems of Tuscany.
      Have a look at the links and get back to me!
      Here are some suggestions for fantastic villas in Tuscany!
      I remain at your disposal,
      Ciao from Florence :-)
      elena

      Reply
      • Elena,

        This sounds fantastic! Would love your help along the way. I forwarded your information to my friends
        who will be traveling with us. We are getting together for our travel discussion. I’m sure I will have a few
        questions in the next weeks/months.

        Best Regards,
        Kathleen

        Reply
  • Hi Elena, my friend and I are traveling to Tuscany for 5 days at the end of this month and we are wondering which places we should visit and would love your help. We are arriving at Rome and planning on renting a car to travel around. We’ve been to Florence before, so we would rather see some smaller towns and villages. Our main goal is to check out a few places, have nice food, visit a couple of wineries and find some gorgeous landscapes along the way. We know 5 days is nearly not enough to see everything, so what would you suggest as places that are must see?

    Thanks so much!

    Reply
    • elena nacci Post author

      Hi! Thanks for getting in touch! I’m happy to help :-)

      The route from Rome to Tuscany is amazing and really offers a lot in terms of scenic landscape and beautiful smaller towns and villages, and of course great food and wines!

      Recently on the blog I’ve written a post that is really made for you :-) On the route from Rome to Tuscany makes a itinerary on the road from Rome to Florence passing through some of the best Italian sights.

      Considering you’re staying 5 days, here are the must see places I suggest you visit:
      -Orvieto and its stupendous Duomo
      -The astonishing medieval hill town of Civita di Bagnoregio, almost a surreal place! I speak about it in this article that lists the most beautiful villages in Italy.
      -The Val d’Orcia and its stupendous hill towns and amazing landscape. Here food is gorgeous and we are in the land of great wines, like the Brunello of Montalcino. A great winery to visit is Ciacci Piccolomini in Montalcino. Villages like Pienza, Bagno Vignoni, Montalcino and Montepulciano are among the most beautiful places in Italy.
      -Then leave the Val d’Orcia to reach Siena, not nay the city of the famous Palio horse race but one of the most beautiful and suggestive art towns in the world!
      -Leave Siena to reach the idyllic Chianti region, renowned for its beautiful landscape and fine wines. Badia a Passignano winery and Osteria is a beautiful place where to eat fantastic food! The same for Badia a Coltibuono.

      You’ll find all these places on the road itinerary from Rome to Tuscany :-)

      Do contact me again for any other suggestion,
      Ciao from Florence,
      Elena

      Reply
  • I am trying to plan a surprise vacation for my wife and daughter this July (~11 – 23rd) and have two questions, if you’d be willing to share your insights:

    1) would Castello di Casole be a good base from which to explore Tuscany for say 6-7 days (we don’t like changing hotels frequently); and 2) where else might you recommend we go for the remaining 4-5 days? My daughter is 13 and we’re very interested in creating special memories and finding activities the whole family (3 of us; wife and I are ~50) can enjoy.

    Many, many thanks! Paul

    Reply
    • elena nacci Post author

      Dear Paul,
      Tuscany is the perfect destination for a surprise vacation :-) You will all really enjoy the place!
      The beautiful Castello di Casole can be a good base from which to explore Tuscany. I imagine you will have a car, by which you’ll be able to move everywhere you like. In less than one hour, you can go visit Tuscany most popular sights, including Volterra, San Gimignano, Chianti, and Siena. Florence is around one hour away, while in less than 1 hour and half you can reach the Val d’Orcia area and its stupendous hill towns like Montalcino and Pienza.

      Tuscany is the right place to enjoy a lot of fun activities, like horseback riding, cycling, having fun at the seaside and at amusement parks. Take a look at this list of the things to do in Tuscany to get some ideas.
      Florence is a fantastic art town with a lot of great activities for all the family, have a look here.

      As you’ll come here during summer you may consider spending the remaining 4-5 days on the coast or near it. You may move more south of Tuscany in the beautiful Maremma area, renowned for its verdant landscape, wild nature, and enchanting coast with clear waters. Monte Argentario can be an idea! deep blue sea, scenic landscape, beaches, and a lot to see and to do! The Natural Park of Maremma, the splendid Tuscan islands, enchanting fishing villages…Moreover you can make day trips to very interesting hill towns like Capalbio, Scansano, Magliano in Toscana and a bit further away (1 hour) reach the amazing surreal town of Pitigliano :-)

      I remain at your disposal for any other help you may need,
      Enjoy planning your trip,
      elena

      Reply
  • Hi Elena,
    I am so happy that I found your blog and posts!
    My husband and I are planning a 10 day trip (plus or minus a day or two) to the Tuscany region this July.
    We honeymooned on the Amalfi coast last September, and we LOVED our trip. Our favorite part was being able to go from town to town stopping for a cappuccino, looking at unique wine stores, having delicious lunches, and just enjoying the area. We love cute, small towns!

    My best friend is getting married in Pienza, where we will spend 2 nights after 2 nights in Florence. I would love your recommendations for other areas to stay in that have cafes, shops, etc. We would like to stay at 1 or 2 more locations. I would also LOVE to see Cinque Terre for 1-2 days, but I am ambivalent to take away time from another area in Tuscany if there is more to explore!

    My hope is to stay in a town that has the option of strolling around, eating, shopping, etc. and that is also drivable to other appealing areas in Tuscany. By the way, we will have a rental car, so that will help!

    We would love any guidance!
    Thank you again for your wonderful blog and providing us so much information.
    -Emily

    Reply
    • elena nacci Post author

      Ciao Emily!
      Thanks for getting in touch! The Amalfi Coast is incredibly beautiful, I love it :-)

      Be sure you will both fall in love with Tuscany too!
      The medieval town of Pienza is delightful! Views, atmosphere, shops, food…all is fantastic! Another great hill town with cafes and shops is Montepulciano, that you may visit while in Pienza, together with the many others charming medieval towns of the Val d’Orcia area: Bagno Vignoni, San Quirico d’Orcia and Montalcino. Another wonderful area is near San Gimignano, the famous medieval village with towers. I would stay right in San Gimignano or its fine countryside, and from there explore Pisa, Lucca, Volterra, Monteriggioni and Siena. Here is a full list of the day trips you can make having San Gimignano as your starting point. As your third location I would consider the Chianti wine region and its villages, and from there go visit Florence and its many sights and beautiful shops! While, in case you decide to visit both Florence and Chianti while in San Gimignano, which actually makes sense, you may also consider Cortona as another possible location. Cortona is an ancient Etruscan town full of lovely shops and cafes, and serves as a good base to visit both Tuscany and Umbria.
      Take a look at the pics of the various destinations and choose on the bases of what inspire you the most!
      Let me know in case you have any other question,
      elena from Florence

      Reply
  • Kathleen Tuffner

    Hello Elena,

    I’m back with questions from the Windy City! We have booked a week in the Chianti area as you had suggested for the day trips in the Tuscany region.
    We are planning on staying three nights in Florence at The Hotel Hamilton.We have not booked yet. Do you have a central location recommendation for Venice? We plan on staying three nights the last part of our trip.

    Best Regards,
    Kathleen

    Reply
    • elena nacci Post author

      Hello Kathleen,
      Good morning from Florence! Glad to hear from you :-)

      You will enjoy the Chianti area!
      Venice is stunning, it’s great you’re going to visit it. Here are my recommendations for charming hotels in Venice:

      Novecento Boutique Hotel, a lovely boutique hotel with a very central location near St Mark Square
      Hotel Rialto, charming 4 star hotel overlooking the Canal Grande

      For further suggestion, just get back to me!
      Have a nice day!

      Reply
      • Dear Elena,

        Thank-you for the Venice hotel recommendations. You are a lovely woman!

        Enjoy your week-end.
        Kathleen

        Reply
  • Hello Elena,

    Thanks a lot for the information you provide, it has proved to be very useful but, please, could I ask for your advice?

    After visiting Firenze we have 6 days until getting our flight back. We don’t like very much to make loops, it’s certainly more comfortable to stay in the same hotel for more than one night but, in order to reduce km (and fuel!), we prefer to make a straight route whenever it’s reasonable.

    According to the selection we have made, how could we DIVIDE the route appropriately?

    – Firenze > Chianti region:Strada, Greve, Panzano, Radda, Castellina, Siena
    – Vall d’Orcia: Siena, Montalcino, Sant’Antimo, Rocca, Bagoni Vignoni, Monticchiello, Montepulciano, Pienza, San Quirico,
    – Crete sinesi
    – Monteriggioni, San Gimignano, Volterra
    – Pisa, Lucca > Firenze

    Thanks a lot and kindest regards,

    Andrea

    Reply
    • elena nacci Post author

      Hi Andrea,
      Thanks for getting in touch! I’m glad to help.
      Actually the itinerary covered in this blog post is quite challenging, as one has to change base quite often. Maybe you could narrow it down to 1 or 2 different places as your base, in addition to Florence of course.
      How many days are you staying in Florence? I’m asking as I would visit both Pisa and Lucca on a day trip from Florence, you can do Pisa in the morning and Lucca in the afternoon. I would instead visit both San Gimignano and Volterra from Chianti, that you might consider as your next base after Florence. The Chianti area has a central location in Tuscany and is perfect to make explorations. While in Chianti do visit all the villages and other attractions of the area itself, San Gimignano and Volterra in one day, Monteriggioni, and Siena. You may stop first in Monteriggioni and then in Siena on the day you’re leaving Chianti to reach the Val d’Orcia, that I would make as your next base. You could stay in Bagno Vignoni or in Pienza, both beautiful places to stay. From there visit Montalcino, Sant’Antimo Abbey, Rocca d’Orcia, Bagno Vignoni, Monticchiello, Montepulciano, Pienza, San Quirico d’Orcia. I would actually explore the Crete Senesi while you’re based in Val d’Orcia, so to have more time to travel this other beautiful area of Tuscany.

      If you have any other question do not hesitate to come back here!
      Happy Planning!
      elena

      Reply
  • Hi Elena,

    Your blog is really so informative and helpful for first time travellers, just to share my itinerary with you: i m spending almost 3 nights first in Pisa, where i plan to do 1 day trip to CT while there and 2 days in & around Pisa.

    Next we go to San – gimignano for 2 nights and explore the area around, 3 nights next in Florence and do the same. finally 2 nights in Siena and return back to Pisa for flight back home.

    How does the plan sound? would you recommend changing anything here or visiting the same places in a different order so so.

    question for me would be:- how is the option of doing 1 day trip to CT from Pisa sounds like?

    Reply
    • elena nacci Post author

      Hi Joydeep,
      Very happy you find my blog informative and helpful :-)

      Your plan is good, though I would stay one night in the Cinque Terre and one less night in Pisa. The cinque Terre can be easily reached from Pisa also by train but I a night there is recommended. The rest of your days are planned well.
      My articles about San Gimignano as a base, Florence as a base and Siena as a base can be useful :-)

      Feel free to ask any other question,
      Have a great holiday,
      elena

      Reply
  • Hi Elena,

    Thanks for all the great tips and information on your blog! We’ll be spending 7 nights in Chianti and Val D’orcia area. We’re thinking of driving from Cinque Terre or Florence – Where do you suggest we rent a car and route to avoid the ZTL zones and heavy traffic driving?

    For the drive to Val’Dorica (we’ll be staying near Montepulciano), do you suggest SR2 via Cassia or SS438 route?

    Thanks very much.

    Reply
    • elena nacci Post author

      Hi Bonnie,
      thanks a lot for your message.
      In case you’re driving from the Cinque Terre you may well reach La Spezia by train and rent your car there. If you’re driving from Florence you can rent your car at a location outside the city center, like in Via del Sansovino, for instance.
      For the drive to Val d’Orcia I would run on the scenic SR2 via Cassia and stop here and there to see the landscape.

      For any other question, I’m here :-)
      have a great Tuscan stay!
      elena

      Reply
  • Hi Elena
    Thanks for the useful information, a very informative read.
    Please can you provide me with some additional thoughts to an itenaray I’m trying to pull together for a 2 week stay as first time visitors to the Tuscany region for an upcoming 50th birthday holiday.
    So far thoughts are flights into Pisa travel by train to Florence. Stay 5 nights using Florence as a base using the train to get to places worth a visit, (? Ideas) including doing a bike tour of a vineyard, then travel by train and stay in Cinq Terre for 5 nights walking between the 5 villages but using one as a base, also thought would take a ferry to Portovenere and perhaps a train to Sestri Levante but then would be open to advice for last 4 nights conscious need to travel back to Pisa for flight back really want to avoid hiring a car but want to make the holiday special I would really welcome your advice. Thanks Sue

    Reply
    • elena nacci Post author

      Hi Sue,
      I’m happy to help.
      You can avoid hiring a car but still have a special holiday :-)
      Florence is the best place to stay as a base when not having a car. From Florence you can reach a lot of beautiful places in Tuscany and make very interesting day trips around the region. Here you can find all useful info for doing the best day trips from Florence using public transportation.

      The Cinque Terre can be conveniently reached by train, and once there you can still move from one place to another still using the local train.
      The same for coming back to Pisa, still by train.

      Feel free to contact me again,
      Have a nice day,
      elena

      Reply
  • Hi I would appreciate your thoughts on our two week trip to Tuscany in September. We arrive and depart from Pisa airport. The options are to take a train to Florence for 2 or 3 days and onwards to Lucca where we will hire a car and stay for maybe 3 or 4 days to explore the northern part of Tuscany. From Lucca, we will travel south and base ourselves in Chianti or Sienna for the remainder of the two weeks. I know it is not a good idea to take a car to Florence which is why I am thinking of doing it this way – but your suggestions will be welcome. We want to get the most out of our first time to Tuscany. Many thanks.

    Reply
    • elena nacci Post author

      Hi Miriam,
      I’m here after a very long pause, sorry!
      What about your trip to Tuscany?

      Reply

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