Private Siena and San Gimignano Tour: Explore Medieval Hill Towns with Wine Tasting in Rome

Discover the charm of medieval hill towns with a private tour from Rome. Explore Siena and San Gimignano, indulge in wine tasting, and enjoy a memorable day in the enchanting Tuscan region.

Duration: 11 hours
Cancellation: 24 hours
Highlights

At 7:30 am, an English-speaking driver will collect guests from their accommodation in Rome and transport them through the picturesque Tuscan countryside. After approximately a 2.5-hour journey, they will arrive at the charming town of Siena. In Siena, there will be free time to wander and discover the town’s hidden gems, from Piazza del Campo, known…

What's Included
  • Private tour
  • Driver
  • Live commentary on board
  • Hotel/port pickup and drop-off
  • Transport by private vehicle
What's Not Included
  • Gratuities
  • Food and drinks, unless specified
  • Price doesn’t include wine tasting and light lunch (as above 55€ p.p.) to be paid on site
  • Alcoholic beverages
Additional Information

Discover hill towns, medieval sites, and exquisite wine on this delightful tour from Rome. Starting with a hotel pickup at 7:30 am, an English-speaking driver will guide you through this captivating region. After a 2.5-hour journey, arrive in Siena and enjoy some leisure time to explore this charming town. Next, proceed to Gimignano, where you can…

Location
Piazza del Campo
Piazza del Campo,
Cancellation Policy

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

Customer Ratings
5.0
(20 Ratings)
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1 star
Teammom1811
Oct 21, 2025
Great tour - What a great tour and Fabulous guide.Probally best tour guide we have ever had. He was prompt, thoughtful exstremly knowledgeable and so very entertaining in conversation. The places we went were just stunning.
Review provided by Viator
C956dclaurap
Jun 23, 2025
Great winery excursion - Didn’t know what to expect with this excursion but overall was amazing. The winery was top notch. Lasagna was amazing!! Sienna and San Gimignano were both cute towns we would love to go back and explore more. Diego was our driver and he was funny and knowledgeable. Highly recommend!
Review provided by Tripadvisor
E4885lylisat
Dec 3, 2024
DON'T WAIT BOOK YOUR TOUR WITH ROME PRIVATE EXCURSIONS 5 STAR - I can't say enough about this experience. First, our guide/driver Manny is the very best guide in all of Italy. Friendly, knowledgeable and prompt. Clean, comfortable car. The visit to both Siena and San Gimignano were amazing, but I can't say enough good things about the winery experience. Far exceeded any wine tasting I've ever done in Napa, Sonoma or even France. Amazing wines, wonderful food, beautiful scenery. If you are considering booking a private tour in Italy, Rome Private Excursions is the very best. I've also experienced their full day Private Tours in Rome including the Vatican and Colosseum, Florence with the Academy and Luca/Pisa full day trip. Also, one of the best parts of working with Rome Private Excursions is the excellent communication before and after the tour. You never have to worry about being picked up. Simply perfection.
Review provided by Tripadvisor
F9205tlpatrickb
Sep 19, 2024
Visit to Tuscany - We had a fabulous time on our excursion with Fabio. Fabio is a safe and competent driver. He made great conversation with my wife. His directions at each stop were very clear and helpful. We had never been to Sienna or San Gimignano before. Now Sienna may be my wife’s favorite town in all of Italy. The wine tasting at Tenuta Torciano was fun and relaxed. All in all it was a wonderful experience.
Review provided by Tripadvisor
Tony_p
Jul 5, 2024
Excellent - We went to Tuscany and had wonderful drivers to show us me and my family a great time. I highly recommend this tour.
Review provided by Viator
Anna_m
Jul 5, 2024
The best tour! - Luca and Manni were the best! Definitely recommend taking this tour! They were very knowledgeable. The drive was very pleasant-able.
Review provided by Viator
Karajcon
Jun 10, 2024
Professional, fun experience! - We had an amazing tour of Siena, San Gimignano with a wine tasting at Tortiano winery. Our driver was very professional and filled us with fun facts throughout the day. He offered great suggestions for places to experience the local culture in each of the towns. It was a wonderful day and we left wanting to experience more. We will use this tour company again!
Review provided by Tripadvisor
Delaneynation
Jul 10, 2023
Life changing! - Luca was absolutely incredible on our wine tour from Rome. He took us to the best wineries in the area and made sure we had everything we needed at all times, also was extremely knowledgeable and was able to answer any questions we had. The van was also in great condition and extremely clean so it made for a smooth and pleasant transfer. Can’t say enough great things about this experience! Truly life changing!
Review provided by Tripadvisor
Tj857
Apr 20, 2023
10/10 ⭐️ - Luca, Manny, and Johnny treated us from the very beginning like family and are unbelievably knowledgeable of every thing you pass by in Italy! They know all of the goods spots and even translated for us often to make sure we were taken care of. You may even get Luca to sing for you in the van. 🥳 10/10 ⭐️
Review provided by Tripadvisor
Stlchesterfield
Apr 2, 2022
Highly recommend! - The entire experience was fabulous! Manny was an excellent driver and so informative! He was patient with our group and all of his suggestions were amazing! Wine tasting was wonderful and so were all the amazing sites!
Review provided by Tripadvisor
From $182
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).