Siena & San Gimignano: Medieval Wine Adventure

Embark on a full-day Tuscany wine tour from Rome, discovering the enchanting cities of Siena and San Gimignano. Explore the medieval streets, savor local sweets and wines, and indulge in a delightful lunch in a famous cellar.

Duration: 10 hours
Cancellation: 24 hours
Highlights
  • Basilica Cateriniana Di S. Domenico - The Basilica of San Domenico is located on the slopes of the historic center of Siena, framed by the houses that “climb” under the Duomo, it is among the most important churches in the city especially for its link with the life of Saint Catherine of Siena. Built between 1226 and 1265 and enlarged during the…
What's Included
  • Free transfer in air-conditioned minivan
  • Free pick-up and drop-off at hotels, apartments, B&Bs
  • Semi-private tour experience
  • Guided tour throughout the trip
  • Wine and local product tasting in a famous cellar
  • Visit San Gimignano, the city of 100 towers
  • 2-hour visit of Siena with tour leader
What's Not Included
  • Siena Cathedral entrance tickets
  • Tips
Additional Information

Embark on a delightful full-day excursion from Rome, traveling through the picturesque Chianti hills to explore the enchanting cities of Siena and San Gimignano. Siena, a stunning medieval city in Italy, invites visitors to its vibrant heart and the central square, “Piazza del Campo,” renowned for hosting the famous Palio, a medieval-style horse race….

Location
Basilica Cateriniana Di S. Domenico
Piazza San Domenico,
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(111 Ratings)
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Nora_s
Nov 7, 2025
Amazing Tour - Amazing tour. Our guide, Stephano, was amazing, very knowledgeable and sweet. The wine testing was incredible.
Review provided by Viator
Nina
Nov 6, 2025
Best Service - This is a top notch experience, especially if you don’t have enough time to viisit Siena and Tuscany. Giuseppe and Luigi once again provided excellent service, very accommodating, flexible , with a personalized service! Wine tasting with lunch at San Gigmiano was the best ever! This is a must in Tuscany! Once again our tour guide and driver delivered the best service! Thank you Welcome Italy
Review provided by Viator
Janessa_t
Nov 3, 2025
Stunning - This tour ended up being just me and my husband with our guide, Pino, and our driver, Artur. From the moment we left Rome for Siena, we were already joking around like we’d known them for years. Pino (also known as Giuseppe, Joseph, or Pepe—take your pick) was funny, entertaining, and ridiculously knowledgeable. Siena is small but full of surprises. We learned so much about the life of St. Catherine of Siena without anything feeling too serious or museum-lecture heavy. Lunch at the winery was delicious and definitely catered to carnivores—but don’t worry, they’ll throw some vegetables at you too if that’s your thing. San Gimignano is stunning, like a medieval fairytale village that somebody forgot to turn into a movie set. Amazing day, great company, and honestly, it felt more like a road trip with friends than a tour.
Review provided by Viator
Elizabethr_r
Oct 14, 2025
Awesome Tuscany Winery! - Tour manager Teresa & driver Roberto were fantastic! From the time they picked us up at our hotel to the time they dropped us back off, they took great care of us. Teresa was very knowledgeable, professional and courteous. She ensured our safety and that we were enjoying ourselves. The trip there & back was planned & coordinated to perfection! The wine was great & the food was delicious. Thank you Teresa for an amazing & awesome experience!
Review provided by Viator
James_s
Oct 1, 2025
We had a great time. My... - We had a great time. My wife 😍 needed to walk slowly with a cane and she was not rushed or left behind like many other tours. Our guide kept everything at her pace. Great job!
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Stephanie_b
Sep 8, 2025
Fantastic experience - This experience was amazing! Can’t call it anything else. Big shout out to Sam and Roberto our guide and driver who were excellent. There are a lot of steep areas but Sam gave us plenty of time to do these. Take/ be prepared to buy a lot of water as we had a very hot and humid day but the towns were beautiful and so worth the drive and the walking. Wine tasting was an excellent way to end the day.
Review provided by Viator
Lisa_d
Aug 24, 2025
Sampling tuscany - Beautiful drive to Tuscany. Walking through the towns was like walking through a history book. Finishing the day with a light lunch and a wine tasting was a perfect way to experience Tuscany. It was an easy drive from Rome. Sam and Jordan were awesome guides
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Cynthia_m
Aug 16, 2025
Visit to Siena - Our driver Pietro was an excellent driver. Our tour guide Antonette was very knowledgeable and cordial,
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Christine_m
Aug 8, 2025
Do it! Amazing! - Artur and Monica are the best!! I can’t recommend this tour enough! Please Do it. Totally worth it. They are attentive and very informative. I am so glad I did this tour! I was sick the day of my original tour reservation. They worked with me and rescheduled my tour for the next day! I’ve used this company many times in many cities. Always a good experience!!
Review provided by Viator
Beth_w
Aug 6, 2025
Perfect day touring Tuscany - Amazing tour! So happy to get out of the city and enjoy the beautiful countryside of Tuscany! Do not hesitate to book this tour! Interesting, fun, and incredible tour guide Monica! Perfect day!
Review provided by Viator
From $195
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).