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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: 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 Complex Pass (OPA SI Pass)

2. 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: Day Trip Pisa, Siena & San Gimignano w/Lunch

3. 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.

Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

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

5. 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 pre-reserved 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.

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

6. 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 Siena: Pienza and Montepulciano Small-Group Tour

7. From Siena: Pienza and Montepulciano Small-Group Tour

Travel along one of the most panoramic roads in Tuscany, driving the characteristic moonscape of the Crete Senesi en route to the medieval hamlet of Pienza in the Val D’Orcia valley. One of the first towns to be entirely planned on paper by important architects and artists of the time, Pienza was commissioned by Pope Pius II - the humanist pope - to help him renovate his native town and bring it to new splendor. A wholesome lunch, based on fresh local ingredients will be waiting on a beautiful terrace (weather permitting) at a local dairy farm. Learn about the process of making Italy’s famous pecorino cheese. Continue in the afternoon to Montepulciano, one of Tuscany’s largest hill towns. Under the dominance of Siena in the Middle Ages, and Florence during the Renaissance, today it is renowned for its wine. See influences from both towns in the architecture and art of the historic center, located on a steep hill with beautiful views of the Tuscan and Umbrian border. Go to the main Piazza Grande, and tour one of the many wineries, carved out of the earth below the city. Discover some of the palaces of the noble families that once lived here. After a short walk around town with a guide, enjoy some free time to taste the fabled wines, or continue to explore the palaces, churches and streets on your own. As you follow the route of the main road downhill, imagine how hard the “Bravio delle Botti” festival must be; a competition to race wine barrels from the bottom to the top of the hill!

Siena: Palazzo Pubblico Entry Ticket

8. 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. 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.

Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

9. Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

Discover Tuscany on a guided day tour from Florence to the medieval cities of Siena, San Gimignano, and Monteriggioni. Enjoy views of rolling hills and vineyards, with a stop at a Chianti winery for a traditional Tuscan lunch and wine tasting. First arrive in San Gimignano, a tiny medieval town that has remained intact through the centuries. Sitting upon a hilltop, it is famous for its numerous towers, frescoes, and other art treasures. Enjoy more free time to discover this fascinating city on your own. Next, visit the charming historical hamlet of Monteriggioni, a medieval village enclosed by its famous walls, which remained standing to this day. Afterward, you will cross the Chianti rolling hills and then arrive at a small and typical winery. There, taste 4 wines, and sample balsamic vinegar and other locally produced products. Your final stop is in Siena, where you will have free time to walk along the narrow medieval streets, admiring the splendid palaces, the Cathedral, Libreria Piccolomini, and the famous shell-shaped Piazza del Campo.

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

10. From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

Enjoy the beautiful Tuscan landscapes on the way to the famous wine hill of Montalcino with your guide. Learn about the process and passion involved in creating the famous Brunello Wine, and enjoy a local lunch. First, walk in the vineyards and explore the cellars where the wine is produced and aged before enjoying an introductory tasting of the world-famous Brunello wine. Then visit the hilltop town of Montalcino. See the town's medieval fortress, and spend time browsing the shops and streets. Take in the incredible views of the valleys and vineyards below. Next, enjoy a traditional Tuscan lunch at a family-run winery, accompanied by the delicious wines produced at the facility. Next, continue to the stunning and ancient Benedictine Abbey of Sant'Antimo, a special place set in a breathtaking landscape. In the afternoon, visit a third winery where you’ll get a detailed description of the wine-making process. Learn how the vines are cared for and about the long aging process in oak barrels. After visiting the cellars and getting to know the winemakers, you’ll sit down for a final tasting before the return drive to Siena.

Available activities

  • Exploring Siena
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  • Day trips from Siena
  • Tuscan wine & vineyards
  • Italian food & markets
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What people are saying about Siena

Overall rating

4.5 / 5

based on 15,029 reviews

The whole trip was a dream, the guides where very accommodating and even when I was late due to transport issues, they were kind enough to wait for me. I loved the whole itinerary and the information provided was very insightful and useful, I loved it all from start to finish.

The tour guide was great. Very informative and you could tell he loved his job. Lunch at the winery was delicious, and wine was excellent. Great tour would definitely recommend.

Great day out. Our host Angela was brilliant. Nando the driver was fantastic. We also had a great local guide in Siena called Donatella. Definitely recommend.

Great trip. Amazing places. Alessandro was great and explain everything. and the wines were superb

It was a relaxed day trip. I am glad to have booked it.