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Siena Tours

Our most recommended Siena Tours

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 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.

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. 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.

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

3. 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.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

4. 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.

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

5. 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.

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

6. Florence: S. Gimignano, Siena, Chianti Lunch & Wine Tour

Embark on a scenic guided tour from Florence to the charming Tuscan towns of San Gimignano, Monteriggioni, and Siena. 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.

Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

7. Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

Discover the beauty of Siena during a 2-hour walking tour, one of the world's most well-preserved medieval cities. Walk the narrow cobblestone streets and marvel at the architecture. Visit the Basilica di San Domenico and learn more about St Catherine, patron of Italy. Learn about the grand history of this proud Republic and discover the traditional Palio, a spectacular festival that features a wild bare-back horse race around Piazza del Campo, the city's central square. Learn about the Contrade or city neighborhoods and how they wait all year to participate in this fundamental race. Visit Siena's historic city center, a UNESCO World Heritage Site, to marvel at the magnificent architecture of Palazzo Salimbeni, today the world's oldest Bank, attesting to the wealth and trade of its glorious past. See Palazzo Tolomei, an imposing private Gothic building and the main square with its monuments and fountain. Discover the culinary traditions of the town and finally walk to one of the most spectacular cathedrals in Italy, the Duomo of Siena.  Your English-speaking local tour guide will escort you inside the Siena Cathedral to visit the chapels and to see the impressive masterpieces by Donatello, Michelangelo, and other artists, an unforgettably rich building of centuries of art and devotion.

Small Group E-Bike Tour with farm lunch from Siena

8. Small Group E-Bike Tour with farm lunch from Siena

Meet your guide for the day in front of the pharmacy next to the main entrance of Siena's train station. Familiarize yourself with the E-Bikes and equipment before heading out into the Chianti, one of the world’s most famous cycling areas! The assistance from the E-bikes makes biking in Tuscany accessible to all! Easily set the difficulty of your ride and decide whether you would like the bike to do most of the work, or do the workout yourself. The silent electric motor, allows you to enjoy the smells, sounds and tranquility of the Tuscan countryside. Finally begin your ride on secondary roads with limited traffic for a 20km long cycle. During the 3 hour ride, cross neat rows of vineyards, pretty olive groves, dense and shaded forests, and sleepy villages along the road. Immerse yourself in the traditional Chianti landscape with frequent stops throughout the morning to take in the views, breathe in the clean air and to stretch your legs. Visit a beautifully restored fortress dating back to the 13th century, cited by Dante in his Divine Comedy, an imposing Sienese bastion of defense against rival armies. Monteriggioni is now a fortified town where you can leisurely walk the alleys and squares to take in the medieval charm but also visit the church or local shops of crafts and products. Return to your E-bikes for a short ride to a local farm to sit down to a delicious lunch with local wine and extra virgin olive oil while learning about the local wines. Taste the extra virgin olive oil accompanied by platters of tasty local and seasonal products and traditional wines. After lunch, pedal the last leg back to Siena train station after a rewarding, up close experience with nature and wine, some of the best that Tuscany has to offer!

From Siena: Chianti Farm Cooking Class

9. From Siena: Chianti Farm Cooking Class

Add another dimension to your Siena visit and participate in a 4-hour cooking class conducted in the typical Tuscan style. Discover the secrets of preparing regional dishes from a multi-lingual chef in a professional cooking environment. You’ll learn the techniques of Tuscan cooking, the basic ingredients used in traditional dishes, and the magical way in which local cooks create their delicious meals. From bruschetta to homemade pici to a variety of types of crostini, your class will enable you to bring a bit of Tuscany to your dinner table at home. You’re sure to fall in love with Tuscany through its food!

From Siena: Pienza and Montepulciano Small-Group Tour

10. 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!

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San Gimignano

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What people are saying about Siena

Overall rating

4.5 / 5

based on 3,138 reviews

Our tour guide (Maria Luisa) was great. This was a useful and fun way to explore Tuscany and catch a ride to San Gimignano and Siena. Highly recommend. The lunch and winery are okay but clearly a very commercial/modern enterprise. If you care most about visiting the towns, I’d recommend this tour. If you’re mostly interested in visiting smaller, charming, old wineries in Tuscany, the other tours offered by this vendor are more suitable for those purposes. Either way, I’d definitely use this vendor again!

Wonderful trip! One of the highlights on our trip to Italy! So much information and history. We loved it! Things to note it is a LOT of walking. We walked the 10 minute walk from our hotel to the train station so that added on but we clocked over 20K steps that day. I would say we are fairly average size Americans, my husband is 5'9, I'm 5'6 the bus was a bit of a tight squeeze with no bathroom. If we had been taller or plus sized it would have been very uncomfortable.

A wonderful experience with a wonderful guide and bus driver! Barbara was very warm, friendly, and helpful and took extra measures to ensure everyone was having a nice time. She is a delightful guide and very knowledgeable! Fiorenzo is a very safe driver and got us everywhere on time with no problems. Definitely recommend!

The tour was conducted by Walkabout. It was one of the most organised tour I had in Italy. Guide Lavinya was excellent. Her knowledge in Tuscany region and passion for tour is excellent. Great experience with Wine testing. Good to know the local history of Florence, Siena , San G and Pisa..I highly recommend this tour

The vans were very comfortable. Our driver was a sweetheart. Plenty of time in each area. We left a couple of areas a little early by our choice because the weather was windy and cold. Our driver came each time we called.