Small Group Tour to Siena, San Gimignano & Chianti wine region with wine tasting

Piazzale Montelungo, Firenze FI, Italy

Embark on a full-day adventure to uncover the essence of Tuscany's charm, history, and wine. Discover the allure of two iconic destinations, Siena and San Gimignano, before indulging in a delightful wine tasting amid the rolling hills of Chianti.

Cancellation policy

Review the supplier policy below before booking.

Duration 10h 30m

Duration supplied by the experience provider.

Languages

English, Italian, Spanish

Group size

1–20 travelers

Full description

Your journey begins in Siena, a city renowned for its timeless beauty and rich heritage. Guided by a local expert, you’ll wander its labyrinthine streets steeped in history and culture. Marvel at Piazza del Campo, one of Europe’s most celebrated squares and the stage for the thrilling Palio horse race, held twice annually. Admire the magnificent Siena Cathedral, a masterpiece of Gothic architecture adorned with an intricate façade, exquisite marble floors, and artistic treasures by legends like Michelangelo and Donatello. Immerse yourself in the vibrant atmosphere of this historic city, once a fierce rival to Florence.

Next, travel through the idyllic Tuscan countryside to reach San Gimignano, a hilltop town often called the "Manhattan of the Middle Ages" for its iconic skyline of 14 ancient towers. Explore Piazza della Cisterna and Piazza del Duomo, stroll along charming streets lined with artisan shops, and admire the town’s remarkably preserved medieval architecture. The stunning views of vineyards and olive groves stretching out to the horizon will leave you spellbound, making San Gimignano an unforgettable highlight of your day.


Conclude your Tuscan exploration with a visit to a traditional winery in the Chianti region, where you’ll indulge in a guided wine tasting experience. Savor the rich flavors of Chianti Classico and other local varietals, perfectly paired with regional delicacies like pecorino cheese, cured meats, and bruschetta. Learn the secrets of winemaking, from grapevine to glass, and embrace the traditions and passion that define this celebrated wine region.


Whether you’re captivated by medieval history, architectural splendor, or the pleasures of fine wine, this tour offers a harmonious blend of culture and indulgence. Join us for an unforgettable journey into the heart of Tuscany!

Itinerary

Florence. There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you. 

Siena. Next, you will head to a truly unique, medieval city in Tuscany - Siena! The drive will take about thirty minutes, and then your guide will lead you through the picturesque, ancient streets in the heart of the city until you reach Piazza del Campo. In the largest square of the city, you will meet a local and professional city guide for your included walking tour of Siena. For about an hour, the guide will share fascinating facts about this incredible city (which is listed as a UNESCO World Heritage Site), and you will visit some of the most famous points of interest. The end of the walking tour will lead you to the Siena Cathedral, where you can enter at your own expense to see the breathtaking decorations and unique architecture.

Piazza del Campo, Siena. Your walking tour will begin in Piazza del Campo, a fascinating, oval-shaped piazza in the center of Siena. Not only is this a popular spot for locals to meet up with friends and relax, but it is also home to a historic palio horse race! Every year, the different neighborhoods of Siena join for the epic and exciting horse race. Your guide will share plenty of local stories as you walk throughout the Piazza and see some of the famous monuments. Your professional guide will share information in a way which brings the history of the city to life, in a vivid, storytelling manner. 

San Gimignano, province of Siena. Your journey through Tuscany will continue to San Gimignano, known as the "town of towers," because of its fascinating medieval towers still perfectly intact. The drive will take about an hour, and you will see the stunning "medieval skyscrapers" from a distance as your bus pulls into the historic town. Your guide will lead you past an incredible panoramic viewpoint of the Tuscan hills, then through the ancient city doors. You will have an hour to independently explore the town - walk the picturesque alleyways, visit the Duomo, or climb the tallest tower! 

Chianti Wine Region. After exploring these medieval Tuscan cities, you will undoubtedly be ready for some Tuscan wine! Meet back with your group, and head to a nearby wine estate in the countryside outside of San Gimignano. In about fifteen minutes, you will arrive at this characteristic wine estate, where you will be seated in a modern and beautiful tasting room built into the cellar. Enjoy the delicious wine produced at the estate: during the wine tasting, the wine producer will share the secrets of Chianti wine production with your group. At the end of the wine tasting, you will have the opportunity to purchase bottles as a high-quality souvenir of your incredible day in Tuscany!

Piazzale Montelungo, Florence. End your journey through Tuscany with unforgettable views of the Tuscan hills as the sunsets. The drive will take about an hour, and you will arrive in Florence in early evening. 

What’s included

Included

  • Guide
  • Journey by fully-fitted GT Coach
  • Professional English Speaking Tour Leader
  • Small group Tour
  • Guided tour of Siena with professional guide
  • Visit to a Chianti winery
  • Sampling of wines, extra-virgin olive oil and regional products
  • Free time in San Gimignano 

Not included

  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets

Important information

Meeting point

Piazzale Montelungo, Firenze FI, Italy

Don’t forget

Not wheelchair accessibleComfortable walking shoes are recommended   The given order of the visits may change   Please show up 20 minutes before the tour departure  Times are subject to change due to local traffic conditionsSmall group shared tour with other participantsEnglish Only

Cancellation policy

100% charge if cancelled within 48 hours of start.

Your host

VE

Verified Local Host

With GetExperience since 2026

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