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: Tuscany Day Trip with Optional Lunch and Wine

1. 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.

Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

2. Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

Benefit from fast-track entry to Siena Cathedral and admire the stunning artwork and architecture of its interior. Walk along its ornate marble mosaic floor and visit the Piccolomini Library known for its collection of vibrant frescoes. Skip the line and enter the Cathedral and admire one of the foremost masterpieces of renaissance art and architecture in Italy. Gaze 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.

Siena: Siena Cathedral Complex Pass (OPA SI Pass)

3. Siena: Siena Cathedral Complex Pass (OPA SI Pass)

See notable features of the Duomo of Siena with the OPA SI fast-track entry pass. In addition to discovering the Cathedral of Siena, visit the Baptistery, the Crypt, the Piccolomini Library, and the adjacent Museo dell'Opera, Oratory, and Facciatone viewpoint with one convenient ticket. Enter the Duomo and be amazed by its grand scale as you stroll along its stunning mosaic marble floor. Admire sculptures such as The Feast of Herod by Donatello and St. Paul by Michaelangelo, amongst many 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 Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

4. From Florence: Pisa, Siena & San Gimignano 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.

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

5. 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 opt for a guided tour in your preferred language to learn even more about the historic area. Begin with the visit at 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. After some free time in Siena you'll have lunch in a typical Tuscan winery. Then go ahead to the vineyard, where you can enjoy some local wine and visit San Gimignano, a UNESCO-listed medieval town. Continue to Pisa and to visit its stunning Piazza dei Miracoli. Admire the Baptistery, the cathedral, and, of course, the famous leaning tower.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Guided Tour

6. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Guided Tour

Experience the best of Tuscany on a day trip from Florence. Visit the Leaning Tower of Pisa, the hilltop town of San Gimignano. Journey into the heart of the Chianti region for wine tasting and lunch. Start your tour in Pisa and marvel at the celebrated Leaning Tower. Explore the grounds and see the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Continue to a winery 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. 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.

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

7. 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. 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: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

8. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

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.

Siena: Guided City Tour with Cathedral Skip-the-Line Entry

9. Siena: Guided City Tour with Cathedral Skip-the-Line Entry

Explore the beauty of Siena on a small group or private walking tour. See its famous monuments and hidden treasures with an expert guide. Benefit from skip-the-line entry tickets to Siena Cathedral. Meet your guide at the San Domenico Basilica and admire its Gothic architecture. Follow a winding route to take in panoramic views of the city, including the Duomo and Torre del Mangia. Find out about Siena in the Middle Ages, see the imposing palaces said to be the oldest in the area. Have a break to take in the charm of the 14th-century seashell-shaped square, Piazza del Compo, a UNESCO World Heritage site. Admire the magnificent Fonte Gaia fountain with its side reliefs of "The Creation of Adam" and "The Flight from the Garden of Eden." Learn about the history of the contrada (districts) that challenge each other twice a year during Siena’s Palio horse race. Walk to one of the most typical contrada and immerse yourself in the authentic atmosphere. Follow your guide to see one of the local pastry shops that reflect the glory of Italy in using the centuries-old recipes to make traditional Ricciarelli and Panforte. Finally, explore one of the most fascinating cathedrals in Italy with pre-reserved tickets. Follow your guide to marvel at the magnificent marble mosaic inlay floor, stained glass, and medieval masterpieces by Duccio and Pisano. See the Renaissance highlights: several Donatello, Michelangelo, and Bernini sculptures and frescoes by Pinturicchio in the Libreria Piccolomini. Armed with a wealth of knowledge about Siena, say goodbye to your guide in the square in front of the cathedral.

Historic Siena: Guided Walking Tour

10. Historic Siena: Guided Walking Tour

See the highlights of Siena on a walking tour as your guide tells you about the development of the city over the centuries and you enjoy the spectacular scenery and monuments. As you visit Siena’s major attractions such as the central Piazza del Campo, the Palazzo Comunale, the Cathedral, and the majestic Basilica of San Domenico you’ll learn about each of these sights in depth from your guide. You’ll also hear about the noble families that were instrumental in the history of the city, including the Piccolomini, Tolomei, and Salimbeni, and see their palazzos. You’ll learn about the great tradition of the palio and hear stories of pilgrimage and saintliness that distinguish Siena. You can decide to finish the tour with a visit to Cathedral where numerous artistic treasures are preserved. Entrance to the Cathedral is available at an additional cost. You’ll see works by artists such as Pisano, Duccio di Buoninsegna, Donatello, Pinturicchio, and Gianlorenzo Bernini. During the summer you can also see the marvelous marble floor, which is a unique work in the history of art.

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Frequently asked questions about Siena

What top attractions are a must-see in Siena?

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

One of the highlights of our whole trip to Italy was the cooking class at the beautiful farmhouse with Simone!!!! He was fabulous with our family group of ten and especially with the kids. The homemade spinach ravioli and tiramisu that we made were absolutely delicious!!! I highly recommend this experience if you can!!!!!

Lorenzo is a great and knowledgeable guide. We were around 15 people in tye tour, wish was great! Timing was great too, not rushed, but fast enough to enjoy Siena and San Gimignano. This tour really worth it. Only drawback: the single use earphone set. I didn’t know or I would have brought mine not the generate trash.

This was definitely one of the top highlights of the trip. Jon was a wonderful and knowledgeable guide, and everything was perfectly planned out. We had ample time in each place and at the winery to see everything we needed to see.

Really enjoyed the trip to Siena, Chianti, and San Gimignano. Francesco was an excellent driver and guide, as was Lorenzo in Siena. Lunch in Chianti was delightful.

Fabio was a wonderful guide and very accommodating. The wine tasting and lunch was very good and would definitely go back.