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Things to do in
Siena

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

Our most recommended things to do in Siena

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

1. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and choose a guided tour in your language to learn even more about the historic area. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Begin with Pisa and visit its stunning Piazza dei Miracoli. Admire the Baptistery, the Cathedral of Santa Maria Assunta, and, of course, the famous Leaning Tower of Pisa. After your free time in Pisa, head to a typical Tuscan winery in the Chianti Area and enjoy a delicious lunch with some local wine. Explore the city of Siena and visit to Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. Enjoy your last stop in San Gimignano, a UNESCO medieval town, world-known for its Vernaccia di San Gimignano. The system of towers of San Gimignano tells the glories of the powerful families. Between saffron fields and typical indigenous vineyards, the city knows how to offer postcard views.

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

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

Start in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Add Leaning Tower tickets to your experience. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch 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. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that characterizes this city. At the end of the guided tour, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

3. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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.

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

4. Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

Embark on a scenic guided tour from Florence to the charming Tuscan towns of San Gimignano, Monteriggioni, and Siena, listed as UNESCO World Heritage Sites. Stroll around the historic villages and enjoy a delicious Chianti Hills wine and balsamic vinegar tasting. Upgrade your experience with tickets to Siena Cathedral. Start at San Gimignano, the world-famous walled town located on a hilltop, which has remained intact through the centuries and is known for its tall towers, frescoes, and many other works of art. Take around 2 hours of free time to explore the city center. Visit the historical walled hamlet of Monteriggioni. Cross Chianti’s rolling hills to a cozy winery where you can relax and enjoy three wines and balsamic vinegar, followed by a Chianti-style three-course lunch. Enjoy a guided tour of Siena’s historic center (if selected in the option), starting with the 13th-century Basilica of San Domenico. Stroll along the narrow medieval streets of the city, flanked by splendid palaces and historic shops. Pass through the Piazza del Campo and visit the cathedral, if you select the option.  Take some free time in Siena before returning to Florence. The order of the visit may change.

Siena: Siena Cathedral and Piccolomini Library Entry Ticket

5. Siena: Siena Cathedral and Piccolomini Library Entry Ticket

Benefit from fast-track entry to Siena Cathedral and admire its stunning interior artwork and architecture. Walk along the cathedral's ornate marble mosaic floor, and visit the Piccolomini Library, known for its collection of vibrant frescoes. Skip the line and enter the cathedral to explore one of the foremost masterpieces of Renaissance art and architecture in Italy. Marvel at elaborate altarpieces, a sculpture by Michelangelo, and all manner of ornate decorations scattered throughout its vast interior. Enter the Piccolomini Library, which contains a sprawling series of 10 frescoes by Pinturicchio chronicling the life of Pope Pius II. Gaze upwards at the domed ceiling, masterfully adorned with complex patterns and further scenes from the pope’s life. During your visit, listen to an official audio guide to learn about Siena Cathedral and its history and art. The audio guide is accessed by scanning a QR code on your cellphone on the day of your visit.

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

6. Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

Spend the day discovering many of the main highlights of the Tuscan countryside on this guided tour with a traditional Italian lunch included. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena. Your first stop will be Pisa and the Square of Miracles. See the cathedral, baptistery, and, of course, the famous Leaning Tower. The Leaning Tower is almost 56 meters tall, about 183 feet, and leans at about 4 degrees, making it one of the most famous and iconic buildings in the world.  From Pisa, drive past hilltop hamlets scattered across some of the most beautiful and enchanting areas of the countryside. Arrive at San Gimignano where a traditional Tuscan lunch with wine tasting will be served, if the option is selected. Continue to the preserved medieval village of San Gimignano, a UNESCO World Heritage site often nicknamed the “Manhattan of the Middle Ages” because of its famous tall, narrow towers. Explore the town center and the charming craftsmen shops along the cobbled stone streets and small squares. End the tour in Siena, a hilltop town rich in art and traditions. Stroll the pedestrian historical center and visit the beautiful local cathedral. Take a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo.

From Florence: Siena, San Gimignano & Monteriggioni Tour

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

Experience the charm of Tuscany on a day trip to Siena, San Gimignano, and Monteriggioni from Florence. Try a variety of Chianti wines paired with snacks and admire the picturesque Tuscan hills.  Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT bus. The first stop is at Monteriggioni, a medieval hilltop town that is famous for its intact medieval city walls. After some free time, head to the world famous Siena. Explore the Piazza del Campo, that is known for the Palio Horse Race and for its splendid examples of Gothic civic architecture. Have time to visit the magnificent Palazzo Pubblico.  Arrive in 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 lush landscape. Finally, 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.

Florence: Duomo Skip-the-Line Guided Tour

8. Florence: Duomo Skip-the-Line Guided Tour

Enjoy this informative guided tour exploring the Florentine religious center by walking around all buildings of the vast Piazza del Duomo: Baptistery, Belltower, Cathedral and culminating in the visit of the interior of the Florentine Cathedral Santa Maria del Fiore, one of the largest churches in the world, with its impressive stone pillars, stained glass windows and its sensational dome and its frescoes. On this skip-the-line tour, walk "behind the ropes," a restricted area along the left lateral aisle, taking you to stand right by the high altar with the huge Brunelleschi's dome and its amazing frescoes above your head—a truly special and unmissable experience when in Florence.

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

9. Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

Make the most of your time at the Siena Duomo with an inclusive ticket allowing you to access all areas excluding the rooftop. Discover the history of the complex as you listen to informative commentary on the included audio guide. Enter the Duomo and admire its grand scale as you stroll along its mosaic marble floor. Admire sculptures such as The Feast of Herod by Donatello and St. Paul by Michaelangelo among other artworks which are dotted around the cathedral. Visit the Baptistery of San Giovanni within the Duomo to marvel at the splendid Baptismal Font. From here, head down into the Crypt, the underground quarters that remained hidden for more than seven centuries. Then, stroll through the Piccolomini Library and gaze up at the vibrant and colorful frescoes which adorn its walls. Admire the stunning work by Pinturicchio, which depicts ten episodes from the life of Pope Pius II. Access the Museo dell'Opera which houses a selection of archaeological fragments and artwork once part of the cathedral. See a variety of Gothic sculptures by Giovanni Pisano and paintings by Ambrogio and Pietro Lorenzetti. Head into the Oratory of San Bernardino to admire the collection of the Diocesan Museum of Religious Art, with its core at the upper oratory chapel. Discover a variety of Siennese paintings from between the 13th to the 18th century. Finish up your visit to the complex with a climb up to the Facciatone viewpoint. Be enchanted by the unforgettable view over the city of Siena and the beautiful rolling hills of the Tuscan countryside.                                                                                            

From Rome: Florence and Pisa Day Trip

10. From Rome: Florence and Pisa Day Trip

Explore Pisa & Florence, two of Tuscany's most important cities, on this day trip from Rome. Take a comfortable bus ride and listen to the guided tour that your guide will give you on the bus. You will be traveling along the Tuscan countryside while you learn about this stunning region and its impressive history, which was of great importance to the creation of the Italian language. The first destination is Pisa, and in Piazza Dei Miracoli, you will admire the Romanesque-style Cathedral of the city. In the same square, find the iconic Leaning Tower of Pisa, you must stop to take the famous photo of you holding the tower! Then you will be able to enjoy some free time to explore the city on your own. Next, hop back on board the bus and continue to Florence, a perfect Renaissance city where you will enjoy a panoramic city tour provided by your guide, visiting the important landmarks, like Piazza del Duomo, Mercato Nuovo, Vecchio Bridge, and more. Afterward, you will have some time to go on your own through the city, you can add an audio guide to make the most of your experience. You must try the delicious Tuscan delicacies and desserts before hopping back on the bus.

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Frequently asked questions about Siena

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What are the best day trips and excursions from Siena?

The best day trips and excursions from Siena are:

San Gimignano

Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.5 / 5

based on 15,029 reviews

It was an amazing experience. Melissa was so kind and offered us a ride back after because you definitely need a car to get there unless you use the buses there which is complicated. It’s definitely a good value for your money and we felt very safe with Melissa’s guidance and the views were stunning. Def going back again.

Sara was very informative. Learned a lot about Tuscan history. I like how organised the tour was. If you’re looking to visit a few cities/town Italy with a very limited time, this is the best tour for you.

This was a wonderful day and lovely experience , highly recommend! Plenty of good food and wine at the farmhouse style lunch ; guide did a great job ..one of our favorite days in Tuscany

Excellent outing. Sara did a great job. A great tour guide with a very friendly personality and in depth knowledge of Tuscany. The lunch was very good and well worth the money.

Constantino and the driver were fantastic. The winery stop was better than I thought. San Gimignano views are spectacular. Worth the money and the time.