Siena
Tours

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Our most recommended Siena Tours

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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From Florence: Chianti Hills Wineries Tour with Tasting

4. 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

5. 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

6. 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

7. 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: City Walking Tour with Optional Siena Cathedral Tour

8. 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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From Siena: Chianti Day Trip on a Vespa

9. From Siena: Chianti Day Trip on a Vespa

Cruise along scenic and peaceful roads on a Vespa. Pass through the Tuscan countryside and see working farms. Follow winding roads through chestnut woods, olive groves, and vineyards. The scenic area is also peppered with hidden relics of the past, like old castles, villages, farms, and parish churches. Keep your eye out for these as you ride by on your scooter. Enjoy this experience with your Italian and English-speaking guide, who will take you to small medieval villages situated in the heart of Tuscany. Have the chance to drive an original Vespa or decide to be driven by one of the local partner's expert drivers. The tour along the Chianti hills lasts all day. You will stop at a renowned farm for a wine tasting and delicious lunch.

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Total Immersion Wine Tour in Chianti

10. Total Immersion Wine Tour in Chianti

All the guests will be welcomed at the estate and brought to the roof of the cellar to see the most breathtaking views of the rolling hills at 600 meters above sea level. Here one of the passionate members of the team will provide an introduction to a history of the estate and a small general explanation of what guests will see and what they will be doing in the next one and a half hours of their time. Clients will be able to visit one of the vineyards followed by an explanation of the working process and of organic agriculture with some additional biodynamic techniqes that are often used and practised at the estate. If the weather permits, guests would be offered a glass of sparkling wine or a fresh wine of their choice at the small adjecent terrace built under an oak tree.  The tour will then take everyone to a visit through the gardens of the villa and include a visit of the vegetable garden. The cellar is the next stop, where detailed explanation follows about the harvest and selection of the grapes during the harvest, fermantation, and further aging of the wines. Each step of the viniticulture process is explained in great detail and guests would learn a lot of new and exciting things about how to make wines in the Chianti Classico area. The last stop is a tasting room, where guests will be able to try all 5 products of the estate with the selection of various local cured meats and/or cheeses with bread and olive oil. Guests will also learn particular details about the history of each wine, will learn how to smell and taste it, and what to look for when opening a new bottle of wine. The last exciting detail is the grappa, for those who would like to learn about its production and unique and delicate taste.

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Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.5 / 5

based on 3,138 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!

Amazing immersion in the Italian history, art and cuisine. Perfect combination of sight seeing in 3 "must see" places in Tuscany, complete taste of the incredible food and wine from Tuscany and enjoyable and entertaining guide with Alessandro.

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.