Day Trips to Siena

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Our most recommended Siena Day Trips To

  • Florence: Pisa, Siena, San Gimignano, and Chianti Experience

    1. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

    Your day starts in the morning with a free tour of Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous Leaning Tower. Afterwards, you'll move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. There you will enjoy a typical Tuscan lunch accompanied with a good local wine tasting. Following lunch you will discover one of the most beautiful medieval villages of San Gimignano, or the "Medieval Manhattan, where you can explore the maze of cobbled streets, small squares and many local craft stores. Your exciting day continues with a panoramic view of the true Chianti countryside before arriving in Siena, where if desired, your professional guide will let you discover the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that charac...

    Tour was planned and time was sufficient for cowering Pisa, Sangimignano with wine tasting and Siena tour, Driver was good and tour guide was efficient in explanation and guiding the best possible key locations across all 3 cities

  • From Florence: Tuscany Day Trip with Optional Lunch and Wine

    2. From Florence: Tuscany Day Trip with Optional Lunch and Wine

    Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from eit...

    This was such great value for money. Alessandro & Riccardo took very good care of us on our trip. It was well organised and kept to a timely schedule. Alessandro (guide) is very enthusiastic and has a wealth of knowledge to share. He also makes some great jokes that keeps the information enjoyable rather than a history lesson. Could not recommend more doing this trip as you really get to see all of Tuscany. The lunch will also cater for dietary needs which is great!

  • From Florence: Chianti Hills Wineries Tour with Tasting

    3. From Florence: Chianti Hills Wineries Tour with Tasting

    Immerse yourself in Italy's renowned winemaking culture on this tour. Meet your friendly guide at the local partner’s office in Santa Maria Novella Train Station, then leave the city behind as you head out into the Tuscan countryside. Arrive in the charming town of Radda in Chianti and visit one of the town’s traditional wineries. Enjoy a tasting session of 3 regional wines, then have the opportunity to purchase the wines you’ve tasted as well as other local products including olive oil. Afterwards, spend some free time exploring the narrow streets of the town and peruse the local stores for handmade souvenirs. Later, Continue your tour to the next stop of the day, a traditional farm and winery located in the Chianti Hills. Follow your guide on a tour of the entire winery and learn about the winemaking process from grape to glass. Then enjoy another tasting session of 3 Chianti wines a...

    The guide from the service was just ok. She spoke English and was nice but was quiet mostly the entire bus ride and admitted to knowing nothing about wine. The people at the two places we did wine tours were super nice and knowledgeable. Both in beautiful places. The town we went to was nice but also there was one we passed much closer to Florence that would have cut out a lot of driving. Most of the experience was driving.

  • From Florence: Siena, San Gimignano & Monteriggioni Tour

    4. From Florence: Siena, San Gimignano & Monteriggioni Tour

    Visit three medieval towns and the Chianti area in one day on this tour. First, you will cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT Coach. You will arrive at San Gimignano, a medieval town declared a World Heritage Site by UNESCO. San Gimignano is famous for its white wine, the world-renowned Vernaccia, and its skyscrapers! Take time to wind your way through the narrow streets and admire the landscape. Your tour will make its second stop in Siena. Here you will find the Piazza del Campo, famous for the Palio Horse Race and for its splendid examples of Gothic civic architecture. You can also visit the magnificent Palazzo Pubblico with its Torre del Mangia. Continuing south, the tour will make a stop in Monteriggioni, where the medieval city walls remain intact. The main piazza, the Piazza Roma, is the perfect place to savor the history of...

    Very comfortable bus with an enthusiastic guide. There was enough time to explore the cities on my own. The cities themselves were amazing and the guide added interesting historic information

  • From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

    5. From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

    Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside, followed by a stop in Siena. Here, a specialist guide will lead you on a walk through the city's historical center. Skip the ticket line to see the interior of the magnificent cathedral, and pass through the shell–shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

  • From Florence: Pisa, Siena, San Gimignano, Chianti Wine Tasting Full-Day Trip with Lunch

    6. From Florence: Pisa, Siena, San Gimignano, Chianti Wine Tasting Full-Day Trip with Lunch

    Discover UNESCO World Heritage Sites and taste Chianti wines on a full-day trip from Florence. Visit Pisa, San Gimignano, and Siena, and savor a traditional Tuscan lunch. 

    First, head to Pisa to marvel at the Piazza dei Miracoli, Pisa Baptistery, Pisa Cathedral, and, of course, the famous Leaning Tower of Pisa.

    Continue to a wine villa in the Chianti countryside. Enjoy a tour of the estate and learn about its history in the medieval chapel before your first tasting of Chianti Classico on the panoramic terrace.

    Next, relish a typical lunch accompanied by two of the estate's products, a "Riserva" and an IGP wine. After lunch, relax a while in the villa's luscious gardens before going to the medieval town of San Gimignano. 

    Then, follow the scenic roads to Siena for a tour of the city's monuments and piazzas. Visit Piazza del Campo ...

  • San Gimignano, Siena, Chianti Guided Tour from Florence

    7. San Gimignano, Siena, Chianti Guided Tour from Florence

    Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Departing from Florence by luxury air-conditioned bus, your first stop will be the UNESCO World Heritage Site of San Gimignano, one of the most splendid examples of an Italian medieval town. Distinguished by its famous towered skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Also famous for its Vernaccia di San Gimignano wine, saffron, and precious Santa Fina pottery, it is an excellent place to get acquainted with the Tuscan environment. You will enjoy some free time to stroll through the town on your own and explore its beautiful squares, architecture, churches, and side streets. Afterwards you will head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop o...

    Incredible expérience in a small group with a perfectly managed timing. The tour of Sienna light have been a bit more détailed otherwise everything was well above my expectations ! I definitely recommend.

  • From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Lunch

    8. From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Lunch

    Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside. Continue to Siena, where a specialist guide will lead you on a walk through the city's historical center. Admire the exterior of the magnificent cathedral, and pass through the shell–shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

  • From Florence: Tuscany Highlights Full-Day Tour

    9. From Florence: Tuscany Highlights Full-Day Tour

    See all the treasures Tuscany has to offer with stops at Pisa, San Gimignano, and Siena. Tour the scenic Chianti countryside and enjoy a Tuscan lunch served with local wines.

    Begin with a tour of Pisa and admire the stunning Cathedral, the Baptistery, the Monumental Cemetery, and the celebrated Leaning Tower. Continue to a wine estate or restaurant in the foothills of San Gimignano and enjoy a typical Tuscan lunch with wine tasting.

    After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano, and discover the maze of cobbled streets, small squares, and many local artisan shops.

    Take in the panoramic views of the Chianti countryside, before stopping in Siena. Here, a specialist guide joins the group and leads the walk around the most important squares to the Cathedral. Finish your tour with a coffee and visit ...

    Very nice tour, it is well worth the trip and day around Tuscany. We met Raul the driver and Francisco the tour guide, both of them were very nice, they speak Spanish, French, English and of course Italian.

  • From Siena: San Gimignano, Montalcino & Wine Tasting

    10. From Siena: San Gimignano, Montalcino & Wine Tasting

    The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers, a UNESCO World Natural and Cultural Heritage Site. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and ...

    My wife and I enjoyed the experience. If you want a hardcore wine tour, this is not for you. But if you want a tour of Of beautiful Tuscany, see San Gimignano and Montalcino, and check out a couple wineries, this is perfect. We enjoyed both wineries very much and we appreciated that the driver of our tour bus would stop at picturesque locations so we could get great pics of San Gimignano from a distance and the Chianti valley. It was more of a 10 hour tour than 11 but fun nonetheless.

Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.5 / 5

based on 5,046 reviews

Olivia was an amazing tour guide and really interacted with the group to make you feel very welcomed. Siena was beautiful and the walking tour was very informative and really made me feel like I knew the city better. The lunch at the farm had an unforgettable view!

A super busy day with views and very enjoyable walks. You have time to take souvenir photos and explore each city as you wish. I recommend taking the meal included as it was a great experience and well worth it.

Really good day. Thank you Angela. We had the chance to discover Pise, Siena, San Gimignano in one day. Amazing lunch with view on the Chianti. Angela does everything for customers!

Excellent wine tasting in Montalcino!!!! Lucia’s knowledge of wine and history was enlightening!!! Best tasting ever.

Very well organized. Professional guides. Beautiful places and worth the visit