The Best Day Trips from Siena

In my recent post about the best day trips from Florence, I recommend Florence as a great and convenient base for your holidays in Tuscany, especially in case you prefer using public transport and are not willing to rent a car.

If you base yourself in Florence, you actually don’t need a car, as you can reach almost all major Tuscan destinations and sights by bus or train; though not all of them!

Tuscany by car

In fact Tuscany is quite a large region of Italy, and many of its beautiful and suggestive places can only be reached by car, unless you take advantage of one of the many organized tours.

The best way to travel Tuscany and explore its scenic picturesque countryside is actually by car! Driving along curving roads amid the colorful Tuscan slopes is a pleasant experience! You can stop here and there to take wonderful pics, admire outstanding panoramas, or simply “get lost” to discover new charming and suggestive places off the beaten path.

Siena as home base for your Holiday in Tuscany

In case you are going to rent a car, I suggest Siena as the ideal base for your holiday in Tuscany! Why Siena and not Florence?

First because driving in Florence can be a nightmare! There’s a lot of traffic, roads can be a chaos! you can’t reach all parts of Florence with your own car due to limited traffic areas and car parks are quite expensive!

Second, if you are looking for a more quiet vacation, Siena should be your base. Florence tends to be overcrowded almost all year long, so after all day seeing the sights in Florence or anywhere else you may want to come back to a more peaceful and silent retreat, a relaxing hotel in the countryside, or maybe right in Siena 🙂

Siena rises on a hill and enjoys a spectacular vista, it is immersed in the countryside, enjoys a wonderful and unique landscape. Its medieval cityscape is unique and so extremely appealing… that’s the Tuscan town to fall in love with 🙂

For a very chic and comfortable stay right in Siena’s historic center, find my personal suggestions on Siena best hotels and accommodations.

Here follows a list of our favorite places to visit in Tuscany having Siena as a base. They are best reached by car but you can well use public transportation, mainly bus, from Siena. Find all bus routes from Siena and click the link “Mappa extraurbano Siena” on the right. And here you can check for bus schedules from Siena.

Great Day Trips from Siena

1. Florence, the town of art par excellence

Ponte Vecchio in Florence

Florence is full of art and beauty, a continuous discovery of pieces of art and exceptional sights, even if you just walk the streets of its wonderful historic center. If you come not just to Tuscany but to Italy itself, Florence is a must visit. Discover Florence’s Top Attractions here.

2. Chianti countryside and its hill towns

Montefioralle village in Chianti

Chianti is the scenic country home to the famed Chianti Classico wine, with verdant hills and forests, perfect vineyards, medieval castles, delightful villages atop hills, and, of course, a lot of wineries. If you are a wine lover, Chianti is the perfect place to be, ideal to have wine tastings and enjoy typical Tuscan dishes.

3. Monteriggioni + San Gimignano, medieval gems of Tuscany

Monteriggioni in Tuscany

Monteriggioni has a unique layout and has practically remained as it was in the Middle Ages. Made unique by a circle of fortified walls, bastions, and towers all surrounding its tiny center, with characteristic medieval buildings and houses in stone. San Gimignano doesn’t need any presentation, its striking medieval towers are famous all around the world; but San Gimignano is not just towers, there’s much more to discover.

4. Crete Senesi, land of the moon

Crete Senesi

A real land of the moon in Tuscany, with unique scenic hills running side by side in a picturesque and absolutely unique country; barren slopes and ravines make the landscape sometimes similar to a desert. Lovely hill towns rise here and there dominating the landscape. Here you can taste the precious white truffle. Discover the Crete Senesi here.

3. Montepulciano + Pienza, gems of Tuscany with stunning vistas

Montepulciano panorama, village in Tuscany

Montepulciano is so beautiful and characteristic to take your breath away! as is Pienza, the ideal town of the Renaissance! Just wander their medieval alleys to be enchanted by elegant palaces, lovely churches, and stop at every corner to be filled by stunning spectacular views.

5. Val d’Orcia: Montalcino + Bagno Vignoni

Valdorcia in Tuscany, Italy

The Val d’Orcia is the land of the most beautiful postcards you see of Tuscany, probably the most extraordinary countryside in Italy, a sea of undulating green hills, cypress lined roads, and some of the most beautiful Tuscan hills towns and villages, not to mention the delicious local products, like wine, cheese, olive oil. Set in the heart of the Val d’Orcia, Bagno Vignoni is unique! Its medieval Renaissance pool is its main square, an amazing sight! Montalcino is not just home to the precious Brunello wine, but also a beautiful hill village with an impressive fortress and an amazing panorama.

6. Cortona, Etruscan town with incomparable panorama

The village of Cortona in Tuscany

With a dominant location on the very top of a hill on the border between Tuscany and Umbria, this striking town of Etruscan origin, is simply magical, with one of the most beautiful and vastest panorama in the region! Cortona’s main square is enchanting.

That’s  quite a challenging tour of Tuscany! isn’t it?:-)

Consider that such a travel itinerary requires about 5-7 days, so, in case you have a more limited time to spend for your vacation in Tuscany, or you prefer to spend some more time relaxing or doing some other activity, I suggest you focus on Florence, the Val d’Orcia (Pienza, Montalcino, possibly Bagno Vignoni), and Montepulciano! That’s what you really can’t miss visiting!

Any other day trip to suggest? Enjoy your trip to Tuscany 🙂 Need help in planning your Tuscan Trip? Ask here for a free tailored made itinerary!

A Map of the Best Day Trips from Siena


  • Sherry ha detto:

    Dear Elena,
    I will be in Siena from mid April and all of May. My week will be with language school and my wish is to take tours leaving from Siena on the weekends. I travel by myself and am over 50 and would prefer to be on a tour. This will be my third trip to Siena in one year and am looking to see more of the beautiful region. I have been to San Gemiagno , Lucca and Montepulciano.
    Any suggestions would be appreciated.
    Sherry Enrico Amhaus

    • elena nacci ha detto:

      Dear Sherry,
      Thanks a lot for your message! Siena is incredibly beautiful and it’s a great base to explore really fantastic destinations in Tuscany. Regarding guided tours leaving from Siena I recommend this good agency.
      Among the best day trips from Siena, I’d recommend you visit more of the Val d’Orcia south of Siena (Pienza and Montalcino), Cortona, and the scenic Chianti area northeast of Siena.
      I remain at your disposal for any other help needed!
      Ciao from Florence,

      • jocelyn ha detto:

        Hi Arena,

        We are going to be in Siena for 4 days in April. What is the name of your agency so we can look at the day tours you offer.

        Many thanks

        • elena nacci ha detto:

          Dear Jocelyn,
          thanks for getting in touch.
          The day trips I recommend in the post are my personal suggestions for tours you can do on your own having a car. For organized tours starting from Siena, I recommend the Palio Tours agency, have a look at the options they offer.
          Let me know if I can help with more suggestions,
          Have a great Sunday,

  • Sheila ha detto:

    Dear Elena,

    We will be visiting Italia for the first time in May. The end of our trip will be in CT (departing from Pisa airport return home). The begining 3 days is yet to be organized and your suggestions are appreciated in planning the most suitable route. We will be travelling by foot/bus or train. No car rental. Prefer to arrive at PEG due to prices of flights but not sure if it will be too difficult to get from this airport to surrounding towns via bus or train … One stop that we wish to see is Civita di Bagnoregio, for a quick visit. Is there a travel route that you can suggest for us that allows us to see the Civita and make our way up to CT by the fourth day? There is so much to see but we know that time does not allow it all in one visit, so we would enjoy visiting or staying in towns/cities that offer a memorable Italian experience without too much tourism! Thank you so much!!

    • elena nacci ha detto:

      Dear Sheila,
      thanks for contacting me! I’m happy yo give sone help 🙂

      I understand you’re staying in Italy for a total of 4 days, right? Are you making the route from Perugia or Pisa all by means of public transports? Well, visiting Italy’s towns that are a bit away from the usual tourist trail is not so simple! The fact is that not all destinations, especially those in the countryside and up the hills are reached by public transportation. For this reason, I think the best option is to arrive at Pisa Airport, and start your travel route from there via train or bus.
      So from Pisa to Florence via train, then from Florence to Siena. Once in Siena you can reach the wonderful San Gimignano, the village by medieval towers, with a combination of train + bus. From Siena to Montepulciano by train, then to Orvieto, and once in Orvieto you can reach Civita di Bagnoregio by bus.

      Waiting to hearing from you so to plan your Italian trip at its best 🙂
      Ciao from Florence,

  • Nancy Flynn ha detto:

    We will be staying at an agritursimo B & B near Montepuciano for five days from the 12th of June until the 17th and will be renting a car. Could you tell us of some day trips we could make that would be memorable?

    • elena nacci ha detto:

      Ciao Nancy,
      Montepulciano is a great place to stay in Tuscany, and makes a very good base!

      In addition to the beautiful Montepulciano itself, among the most memorable sights to visit from Montepulciano, I have a preference for Pienza, Bagno Vignoni, Rocca d’Orcia, and Pitigliano.

      Pienza is simply the perfect Renaissance town where the panorama is incredible as well as the food you can enjoy!
      Bagno Vignoni is a very peculiar little hamlet with thermal baths with which I’ve fallen in love with!
      Rocca d’Orcia is an ancient fortress you can climb up to get the most spectacular view all over the Orcia Valley.
      If you don’t mind driving for about 1 hour and 20 minutes, then do go south to reach Pitigliano, one of the most impressive places to visit in Italy!

      Towards the end of this blog post you see a list of the day trips one can take from Montepulciano, have a look,
      Contact me again of you need more help,
      Enjoy your Tuscan stay,

  • walt amses ha detto:

    We’ll be hiking in Cinque Terra, staying in Florence and then spending five days in Tuscany. We’d like to rent a car but we’re unsure of exactly the best way to go about it. We don’t need a car while in Sienna and we’d like to stay in one place and do day trips from there….does it make sense to stay in another Tuscan town? We’d like to minimize the number of transfers we need to make with luggage etc.

    Thanks for any help you can provide.

    • elena nacci ha detto:

      Hi Walt,
      thanks for getting in touch!
      I understand you’re staying in Florence, where of course you will not need a car. But are you staying also in Siena? If the answer is yes, then you can stay in the beautiful countryside near Siena’s town center and do your your day trips by car from there. This way you will not have to change base another time. Also in the case you’re staying in Siena’s historic center, I suggest to move by car. Siena is well connected to other destinations in Tuscany, but the problem is mainly with the bus schedules, and also consider that Siena’s train station is not located in the city center.
      For your 5 days in Tuscany with a car, another possibility could be to base in the scenic Chianti wine region, situated between Siena and Florence. Chianti makes a great base, since it enjoys a central location in Tuscany. Chianti is very convenient to visit many Tuscan sights, like the ones listed here.
      So you have Cinque Terre, Florence, Siena or Chianti, I would not add any more transfers.

      Let me know about your plan,
      I remain at your disposal,

  • charles Michel Dados ha detto:

    Great article and very informative. If I don`t want to rent a car in Siena (as I was just reading another article, that parking can be difficult), do you recommend any day tour operators of the so called `WINE ROUTE` (from Siena) who can give good value for money and well informative tours of the valley?

    • elena nacci ha detto:

      Hello Charles,
      Thanks! I’m happy you like the article 🙂
      The problem with parking in Siena is that its historic center is a limited traffic area, but there are many many parking lots walking distance to Siena’s major sights. So you may also consider renting a car and do the wine route on your own.
      As for day tour operators from Siena, I suggest Palio Tours, agency based in town offering wine tours either to Chianti or to the Brunello area.
      Further options for wine tours from Siena are offered by Viator, take a look here to what they offer.
      I’m here for any further help you may need,
      Happy Easter!

      • charles Michel Dados ha detto:

        Many thanks for the info Elena, still undecided though about pros and cons of hiring a car especially if the hotel is within the city walls. Whether the freedom of being on the road at my own pace, or just sample wine and enjoy the landscape and let someone else worry about driving prove to be more important…
        I guess will see things with fresh eyes when I reach Siena early June, very much interested in Val D`orcia part of Tuscany.
        Once again I appreciate your time,
        Very happy Easter to you too.

  • Babs Prewett ha detto:

    Dear Elena,
    We will be taking a trip in May to Tuscany. We plan to take a train from Naples to Rome-spend two nights and then on to Siena. Hoping to make Siena our home base for 4 nights. W are looking forward to day trips from there. On the list of towns are Lucca, Montepuleiana Sam Gimignano, Cortorna, and it is between Pisa and Assis -which do you recommend? From there, we are off for Florence for two nights, then up to Lake Como for two nights. We will rent a care in Siena for the days trips , traveling by train for the remainder of the trip. From Como-back to Naples. Any suggestions to make this a better trip. Thanks. Babs

    • elena nacci ha detto:

      Dear Babs,
      thanks a lot for your message!
      Sounds like a great holiday plan for your Italian trip 🙂 All the destinations you’re going to visit are beautiful!
      Siena is my most beloved art town and is definitely a great base! I always recommend it to anyone, especially in case you’re moving around by car! So you say which one to choose between Pisa and Assisi…both are wonderful and very different form each other, Pisa is mainly Piazza dei Miracoli and the famous Lening Tower, an incredible piazza with stunning buildings like no other place in the world. Assisi is so different.. very spiritual, scenic, and with breathtaking views, quite hard to decide. You can reach Assisi from Siena in about one hour and half, while Pisa is almost 2 hours driving. So you may visit Assisi while you’re in Siena, and if you will have a bit free time, you might visit Pisa by train from Florence. Fast trains starting from Florence reach Pisa in just one hour. As you see from the list, there’s a lot to visit in Tuscany, also add Monteriggioni, Pienza and possibly Montalcino to your list of the towns to visit from Siena.

      I remain at your disposal for any further suggestion!
      Buon Viaggio

  • ha detto:

    Ciao Elena!!
    I really like your article! It makes Tuscany even more attractive to visit. I am leaving from Padova on 30th April or 1st May to Florence for four days Tuscany visiting. I have visited Florence and Pisa last year. This time I want to see the beauty of Siena and Tuscany sun 😉 Perhaps I will spend half day in Uffizi museum.
    I would like to visit Chianti and Valdorcia from your recommendation. However, I am concerned the difficulites of reaching those places by bus or train because I wont rent a car. Could you please provide some advices? Thanks a lot! Dongmei

    • elena nacci ha detto:

      Ciao Dongmei,
      thanks for contacting me! I’m happy you like the article 🙂

      Chianti and Val d’Orcia are best traveled by car, but you can still visit both areas from Florence and Siena using train and/or bus.
      You already have an idea on where to base for your 4 days in Tuscany? As you intend to visit the Uffizi, you might stay 2 days directly in Florence’s historic center. That is very convenient to reach many sights in Chianti and other special places using public transports, bus or train from Florence Santa Maria Novella Station. Have a look at this useful post on what to visit from Florence using only public transportation. You may spend your other 2 days in Siena, and use buses to reach some beautiful destinations in Val d’Orcia, like Pienza and Montalcino. You may also reach the wonderful and famous San Gimignano still by bus from Siena. Here you can check for bus schedules from Siena to the villages of the Val d’Orcia.

      Of course I need to admit that not all destinations both in Chianti and in Val d’Orcia can be reached using bus or train, and some problems may arise from the bus schedules especially when coming back to your home base in the afternoon.

      A further possibility to tour the region would be to make use of some organized tours; that way you’ll not have to worry about transportation at all!

      For any more question, just contact me again,
      ciao from Florence!

  • Saleh ha detto:

    Ciao elena,

    I enjoyed so much reading your blogs along with the questions and replies, specially this one about Siena. I’m thinking to come to Siena for the three weeks during the month of August and study intensive course for Italian language over there. I’m also thinking to rent a car for almost the whole time or maybe less. My question is, I want to stay during those thre weeks in the countryside of Siena and that’s why I know I will need a car, Can you advice me where excatly should I stay or if you have any recommendations for a places in the countryside who have rooms for rent, If possible, can you give me a short idea about the car rental in Siena. I will be saving my money for the months of May, June and July and spend it al during this month and I dream that it will be my lifetime trip 🙂

    warm regards,


    • elena nacci ha detto:

      Ciao Saleh,
      many thanks for your nice message, I’m happy you enjoy reading my blog 🙂
      Sounds like you’ve fallen in love with Tuscany 🙂 it’s such a beautiful place! and Siena is even more enthralling. I’m in love with Siena!
      Are you attending the Italian language course in the historic center of Siena? I’m asking as in case you’re staying in the countryside near Siena, you will always have to move for the course. In that case I would consider staying directly in Siena and use also public transportation for part of your stay to tour the nearest destinations to the town using the local bus. The car is needed for all destinations that are not easily reached by public transports, or that are a bit too far away from the city. As for places to stay in the countryside near Siena, you may consider the small charming village of Sovicille and its surroundings, about 10 km west of Siena. Here is the official website of the municipality of Sovicille where to find good options to stay. Take a look and let me know,
      Happy Planning and Buon Viaggio!

      • Saleh ha detto:

        I’m in love with Italy almost all my life since childhood. Had the best time of my life in Sicily for a month that’s 2006 and since then I keep coming to Italy at least 3 times a year but never to Tuscany and don’t ask me why as I still don’t know the reason. This time I decided to come to Siena and explore the whole region although I know 3 weeks aren’t enough but I will get a great idea I’m sure for my future visits indeed. Yes I’m attending the course in the language course in the historical centre of Siena. I know the best idea is to find a place in the centre or nearby but the idea is, I want to wame up everyday, switch on my car and drive in the countryside while playing the Italian music, that’s why I want tht countryside. You really helped me a lot by telling which me about Sovicille and that’s what I needed to know. Aprecoate it a lot and hopefully one day we can meet in person to thank you. Wihsing you a great time wherever you are now and if I ever had a question, will make sure to contact you. By the way I already liked your page on facebook, name in facebook is Sam Mendez



        • elena nacci ha detto:

          Saleh thank you!
          I think you will love Tuscany more than every other place in Italy!
          Enjoy planning your trip!
          All the best,

  • Lori ha detto:

    My husband and I and our 3 adult children are planning to visit Tuscany May 30-June 7th this year and have rented a villa near Gaiole. We want to spend one day visiting some of the following: Abbey Oliveto, Sant’Antimo, Montalcino, Montepulciano and Pienza. We realize we may have to prioritize. What do you suggest? Thank-you.

    • elena nacci ha detto:

      Hello Lori,
      Thanks for getting in touch!

      You mean one single day? If yes, I would start the day heading south to reach the wonderful Montepulciano as your first stop, then go west to reach the scenic Pienza, and then continue on to Montalcino in case you’re not too tired. I would concentrate your visit on the hill towns. All these lovely villages are quite small but I suggest you take your time while there.

      Feel free to contact me for any other suggestion,

  • thomas cappiello ha detto:

    Please disregard my earlier question on Siena w/o car as you’ve answered it many times already. Sorry for not doing more investigating before questioning. You are very patient and have great info on your site. Thank you!

    • elena nacci ha detto:

      Hi Thomas,
      Thanks for your nice message:-)
      It’s a pleasure to help travelers, if you have any other question, I’m here,
      Have a great holiday,

  • Sophie Sardi ha detto:

    Hi, my husband and i will be spending 6 days in Siena after have already stayed in Lucca for 3 and florence for 4 days.
    I was originally going to hire a car for three days in Siena to see the surrounding towns but am finding the process of choosing the hire car company quite confusing You mention Palio tours – these are private tours. Are there any other group tours you can suggest, you also said Viator tours. I guess I would like to see as much as possible in the time we are there. I assume the town of Siena itself will take a few days to discover? If we don’t hire a car, then possibly two day tours would be sufficient to see most of what you suggest. Which towns would you suggest we see in those to days? Many thanks for your time. Sophie

    • elena nacci ha detto:

      Hi Sophie,
      thanks for your message.
      Siena is really beautiful and its actually takes some days to discover it all.
      Among the best towns I suggest you visit are Pienza, Montepulciano, and San Gimignano, I would not miss them.
      Here are the tours from Siena offered by Viator, though they don’t cover a lot of sights in one day, actually the same for the Palio Tours. You might contact the Palio Tours for a customized tour or consider renting a car and visit what you most like on your own.
      Tried reserving the car through this site?
      Please ask me any more question,
      Have a nice day,

  • beverley ha detto:


    I have just returned from tuscany and plan to return with my family next year. We want to visit Chianti and Siena from Florence. We have five days so will probably make siena our Base. Do you recommend staying also for a night in chianti or just visit on our way to siena?

    Thank you

    • elena nacci ha detto:

      Hi Beverly,
      I would explore Chianti on a full day when leaving Florence, and so arrive to Siena by the evening. As you see form the article Siena is a great base and offers a lot to discover also in its surroundings.
      Let me know if you need any more help,

  • John ha detto:

    Hello Elena,

    I didn’t see anything about Assisi. I will be in Siena for seven days in mid October and was wondering if Assisi is worth the time to visit?


    • elena nacci ha detto:

      Hi John,
      Oh Assisi is certainly worth the visit, I enlist Assisi among the best destinations to visit on a tour of Italy and among the best day trips to make from Cortona, beautiful hill town on the border between Tuscany and Umbria regions.

      You will need about one hour and half to reach Assisi from Siena,
      Enjoy the trip,

  • Anjum ha detto:

    Dear Elena,

    Thanks for putting this together – it’s been very helpful. We will be in Tuscany for 4 days and thanks to your reco, we’re planning to do Florence, Siena, Pienza+Montelciano but we were also planning to do Cinque Terre as we will have a car. Is it realistic? And would those be the top picks given the limited time?

    Thanks for your help.


  • Tolbert Yater ha detto:

    Dear Elena: My wife and I are planning a trip to the Tuscany region and planning to stay in Siena for four or five nights and would like to arrange two day trips for about 6 hours per trip. How can we find a guide in Siena with a car that could drive us on a private trip for just the two of us. I do not wish to drive myself in a rental car. We also would like about a3 to 4 hour tour of Siena just after we arrive from Florence. Thanking you for your help…Sincerely, Tolbert Yater….Fort Worth, Texas

    • elena nacci ha detto:

      Ciao Tolbert, thanks a lot for coming here 🙂 Staying in Siena is a great choice! Siena itself is so beautiful and thrilling, and starting from there, you can embark o some of the best day trips around the Tuscany region. You could ask the very good Palio Tours Siena agency based in Siena for private day tours. I live in Florence if you need suggestions on where to stay on yours for Florence as well, just ask, for any other tip, I’m here 🙂

  • Grant Mahony ha detto:

    Hi Elena, What a service you offer !! Legend. My mate and I will be travelling to both Florence (my favourite city in the world) and Siena next September (2019). Wanting to get a referral to a good relatively cheap place to stay in Florence near the station, also for Siena and a contact for a day’s wine-tasting tour of the beautiful Chianti region – a 1 man tour guide in his car if possible. Appreciate any assistance you can give us. Cheers Grant ….from Down Under

    • elena nacci ha detto:

      Hi Grant, here I am 🙂 I’m so happy you appreciate the service I offer! Thank you!
      You’re so right about Florence! it’s really an amazing city, always full of surprises, even to me that I’m living there. And Siena…so wonderful and incredible as well! As for your accommodation, do you prefer staying at a hotel or an apartment?
      As for a day’s wine-tasting tour of the beautiful Chianti region, I can recommend Chianti wine tour with driver and Chianti wine tour from Florence.

      Waiting to hearing from you about the accommodations, and if you need any other suggestion about the Chianti tour, just ask:-)

  • Melinda Best ha detto:

    Hi Elena,
    Thank you for writing such a beautiful article with such wonderful information. I am wondering if you or do you know someone (a tour company) who will do a shortish day tour from Siena to Montepulciano with a drive through Val D’Orcia area? Some of the tours I’m looking are a full day but we are hoping to do it in as short a time as possible.
    Cheers, Melinda (from Australia)

Leave a Reply