Things to do in
Siena

Enter the heart of Tuscany and discover its abundant wine, winding streets, and medieval architecture.

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Our most recommended things to do in Siena

From Florence: Siena, San Gimignano & Monteriggioni Tour

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

Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT Coach. Arrive at San Gimignano, a medieval town declared a World Heritage Site by UNESCO. Take time to wind your way through the narrow streets and admire the landscape. Make the second stop at Siena. Explore 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. Finally, visit Monteriggioni and its intact medieval city walls. Then, head to the Chianti area and enjoy postcard-perfect landscapes. Conclude your day at a famous wine estate and taste fine Chianti red wine along with homemade snacks.

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

2. 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.

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

3. 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 — the site of the Palio di Siena horse race — and admire the cathedral's exterior in Piazza del Duomo. After some free time, return to Florence.

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Siena Duomo Complex: Fast Pass Entrance Ticket

4. Siena Duomo Complex: Fast Pass Entrance Ticket

The magnificent complex of the Cathedral of Siena, its Duomo, houses a series of some of the most important monuments of the European artistic panorama. With over a million visitors every year, the Cathedral without a doubt represents the fulcrum of the entire complex, while other significant elements include the Crypt, the Baptistery and the Museo dell'Opera, all part of the impressive mass formed by the "Duomo Vecchio" (Old Cathedral), and the "Duomo Nuovo" (New Cathedral).  Enter the Baptistery of San Giovanni to admire the splendid Baptismal Font. From there, head down into the Crypt, the underground quarters that remained hidden for more than seven centuries. You'll enjoy free access to the Museo dell'Opera, before ending your visit with a climb up to the Facciatone ,where you will witness the most fascinating and unforgettable view over the city and the Tuscan countryside.                                                                                                                                                                            

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From Florence: Chianti Hills Wineries Tour with Tasting

5. From Florence: Chianti Hills Wineries Tour with Tasting

Immerse yourself in Italy's renowned winemaking culture on this guided tour by van from Florence. Leave the city behind as you head out into the Tuscan countryside, marveling at the landscape around you. Visit two local wineries and enjoy wine tastings in both of them, learning about the wine-making process from locals. 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 them. Spend some free time exploring the narrow streets of the town. Continue towards a traditional farm and winery. Learn about the winemaking process from grape to glass. Then enjoy another tasting session of 3 Chianti wines as well as local products. Finally, sit back and relax on the return journey to Florence.

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From Florence: Tuscany Day Trip with Optional Lunch and Wine

6. 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 either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

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

7. 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.

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Florence Cathedral: Tour with Cathedral Terraces and Brunelleschi's Dome

8. Florence Cathedral: Tour with Cathedral Terraces and Brunelleschi's Dome

Explore the marvels of the Santa Maria del Fiore Cathedral in Florence with an expert guide. Learn about the cathedral's construction and artworks, and admire breathtaking views over the city from Brunelleschi's Dome. Begin with a guided visit of the interiors of the magnificent Santa Maria del Fiore Cathedral. Avoid wasting time waiting in the ticket line and enter the Duomo accompanied by a licensed guide. After your quick entry, discover the superb works of art preserved inside the cathedral.  Then, enjoy the chance to go to one of the cathedral's exclusive terraces, where you can take in the magnificent scenery surrounding you, dominated by the amazing Brunelleschi's Dome. Find out about the techniques Brunelleschi used to create this architectural wonder. Without any additional waiting in line, climb even higher up to the magnificent Dome to enjoy a spectacular 360-degree view of Florence.

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Siena: Palazzo Pubblico Entry Ticket

9. Siena: Palazzo Pubblico Entry Ticket

Enter the Palazzo Pubblico of Siena and visit the Civic Museum with this entry ticket. Located inside the Palazzo Pubblico, the Civic Museum is a 13th-century building home to impressive wall-to-wall fresco paintings. Explore the museum to learn about the history of Siena and see precious artifacts. Exchange your voucher for an entry ticket at the ticket office and begin your visit in the Sala del Risorgimento. This room hosts fresco paintings that depict the life of Vittorio Emanuele II, the first king of Italy. Walkthrough the Sala di Balìa and see wall paintings from the 15th-century by Spinello Aretino and Martino di Bartolomeo. Also, see the Sala dei Cardinali where precious carved coffers keep reliquaries. Move forward to the Sala del Concistoro, famous for its Beccafumi vault, and see Taddeo di Bartolo's 15th-century Cappella. Continue on to the Sala del Mappamondo, the widest room of the Palazzo Pubblico and used as the meeting place of the General Council. See the famous Maestà, a Gothic masterpiece painted by Simone Martini. Walk through the Sala della Pace or Buon Governo to see more fresco paintings painted by Ambrogio Lorenzetti. The museum entry ticket also includes a visit to the 14th-century gallery, Loggia dei Nove, which offers a beautiful view of the landscape behind Palazzo Pubblico.

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Siena: City Walking Tour with Optional Siena Cathedral Tour

10. Siena: City Walking Tour with Optional Siena Cathedral Tour

Explore Siena's rich history, culture, and traditions with a local guide. The tour is designed to show you Siena's most intriguing sites in a short period, with plenty of stops for photos along the way. Start the tour with a visit to some of the city’s most significant sites including the Piazza del Campo, Palazzo Publicco, Palazzo Tolomei, Palazzo Salimbeni, and the ancient Banchi di Sopra. Upon exploring, learn which buildings hold UNESCO World Heritage-listed status and why. Continue the tour to the Basilica of San Domenico, which is home to Saint Catherine's relics. Next, stop by the Sanctuary of St. Catherine of Siena, where she once lived with her family. Pass by the Baptistery and the Siena Cathedral (or the Duomo di Siena), and head inside for a closer look (if the optional guided tour option is booked). Inside, admire the array of works of art from some of Italy’s most important artists. 

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Frequently asked questions about Siena

What top attractions are a must-see in Siena?

Planning Your Visit

  • How long to spend in Siena, Italy?

    It is possible that two days in the city is enough, but allow yourself a couple extra days to relax and go for wine tasting in the surrounding countryside of Tuscany.

  • The Palio

    One of Siena’s most famous attractions is the Palio, a bareback horse race held every July 2 and August 16 at Piazza del Campo. Seeing this ancient tradition is a once in a lifetime opportunity. If you’re visiting Siena around these times, however, be sure to book hotels, restaurants, and, of course, tickets to the Palio six months in advance if possible—it’s one of the rare times that Siena will feel very crowded.

Good to know

  • Language
    Italian
  • Currency
    Euro (€)
  • Time Zone
    UTC (+01:00)
  • Country Code
    +39
  • Best time to visit
    Fall may be the best time to visit because of the autumn colors in the countryside. Although you can expect some rain, the temperatures are typically warm, and there are plenty of outdoor festivals to visit.

Other Sightseeing Options in Siena

Want to discover all there is to do in Siena? Click here for a full list.

What people are saying about Siena

Overall rating

4.5 / 5

based on 11,644 reviews

This was an excellent and affordable trip to 3 places throughout Tuscany. When I priced the train to Pisa and back, it was approximately the same cost as this trip. Our tour guide was excellent, the winery that we stopped at was very good and the host was exceedingly entertaining. I do wish we had had more time in Sienna as it was beautiful, but I understand there is a time constraint. Overall, I would highly recommend this tour.

Great trip to see a lot in a relative short time. Tuscan country side, Old towns and good food. Our guide Manolo was great, with a lot of information about Tuscany and Florence and on the way back he went past everyone to answer any questions they might had. Loved it!

Valentina was a very good guide providing all the necessary information for our day tour! We also had a very profesional driver (Raul) The tour is totally recomended! Get the one with the entrance in the Siena included! Thanks you for the beautiful experience!

Great group experience, enough time to walk around and enjoy. Would have liked more time at Pisa, maybe Pisa should be a bit longer, just a suggestion.

Very nice trip! Saw all the sights without worrying about where to go and how to get there. Would book if you get tired of having to plan out your day.