San Gimignano and Siena: Wine, History, and Views

Embark on a Tuscany tour and explore the charming towns of Siena and San Gimignano. Indulge in a winery lunch and discover the rich history and beauty of the region.

Duration: 10 hours
Cancellation: 24 hours
Highlights
  • Florence - Upon meeting the expert guide, an air-conditioned minivan will transport you to the first destination of the day, Siena. The journey to Siena takes approximately 1 hour and 15 minutes. During the drive, the guide will outline the day’s itinerary and share fascinating insights about Siena and Tuscany.
  • Siena - Following lunch, a…
What's Included
  • Professional English speaking tour guide available all day
  • Winery tour and tasting of four wine varieties (adults 18+ only)
  • Comprehensive maps and information on every town visited
  • Hearty farmhouse lunch with vegetarian and gluten-free options
  • Guided walking tour of Siena, including cathedral entrance
  • Comfortable travel with air-conditioned…
What's Not Included
  • Gratuities
Additional Information

Post departing from Florence, your journey continues toward San Gimignano. On the way, you’ll admire the scenery consisting of vineyards and undulating landscapes while acquiring captivating knowledge about this town’s past.
Upon reaching, your guide will lead you to the entrance, post which you are free to explore the enchanting lanes and plazas. You…

Location
Florence
Cancellation Policy

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

Customer Ratings
4.9
(21 Ratings)
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Debbierk5640yv
Apr 13, 2025
A Tuscany Excursion To Remember! - Walkabout Tours is the best! I had a custom tour for my high school group which included teachers and students. What a wonderful experience! We started in the beautiful town of San Gimignano, stopped for a superb lunch at a nearby winery and then continued on to Siena. The group had an amazing time! Our guide for the day was Manolo and he was top notch! He was full of historical facts. He was fun, very considerate, had a good sense of humor and he was very professional. Everyone enjoyed his presentation. Everything ran perfectly on schedule and Manolo managed the tour schedule well. He was very conscientious of every detail and he went well above and beyond our expectations! The entire day was a wonderful experience--one our group will never forget!
Review provided by Tripadvisor
Michelle
Mar 31, 2025
Romantic Tuscany day trip for two! - Our guides Alex and Eliana were outstanding! The whole day was a wonderfully romantic and informative experience. The perfect balance of history, guided tour, and on our own time. The winery was gorgeous, the tasting more than generous, and the food was excellent. I would highly recommend this tour to anyone who wants to experience the Tuscany countryside, learn some history, and have lunch at an amazing winery with some of the best wine made!
Review provided by Tripadvisor
Q141jmchristinel
Nov 11, 2024
Best guide (Stefano) and the most incredible tour - I found Walkabout tours after doing extensive research to find the best private tour in Tuscany. They were hands down the most recommended. And it’s safe to say, they did not disappoint. Stefano was our guide and he was incredible. In all the tours and tour companies we’ve booked in Italy (all private and reputable), this was the hands down the best and most top tier. Stefano was early to pick us up at our hotel in Florence to start our day at 830am. From morning to night, he was the most energetic, knowledgeable and fun guide we could’ve asked for. We went to San Gimingnano, Siena and a vineyard for lunch. We also asked him to drop us off at the very end at a famous leather shop in Florence (in lieu of our hotel) and he made every effort to make it prior to the close. Stefano went above and beyond to make sure Tuscany was the absolute highlight of our Italy trip. Thank you Stefano, and I hope to meet you again!
Review provided by Tripadvisor
Jennifer_f
Oct 19, 2024
Highly Recommend this tour to everyone - Highly recommend this tour as well as our tour guide, Stefano! The day was amazing from start to finish. Stefano made the day even better with all of his knowledge of the region and amazing stories about the history of the area. The stroll around San Gimignano and Siena was so beautiful and fun. The lunch and wine tasting at the organic locally owned winery was amazing. The food, wine and view were 5 stars! This tour is worth every dollar plus more! Definitely book it and if you can, I recommend asking for our tour guide, Stefano!
Review provided by Viator
Jami_c
Jun 6, 2024
Unbelievably perfect! - Our guide Stefano and driver Luca made us feel like family. We spent the day laughing and learning and eating and drinking and exploring. It was the most perfect day. Seeing San Gimignano and Siena with them - and with a local guide and friend Alicia - brought Tuscany to life.
Review provided by Viator
Naomi
Jun 5, 2024
Perfectly organised, relaxed, informative and fun - A wonderful tour- both our driver and guide were knowledgeable, friendly and flexible. They couldn’t have done more to make it an exceptional day- both for having fun and learning about these lovely historical places. There was the right balance of showing us around sharing the history and stories and free time to explore and shop. The view at lunch at the winery was incredible and the food and wine complemented perfectly. I wouldn’t hesitate to recommend this more personalised version as it was easy to be curious, relax and enjoy - an absolutely amazing day!
Review provided by Viator
Debra_e
May 5, 2024
Tuscany Tour - Stefano was a great driver, tour guide. We were given plenty of free time to wander around at each village. Despite the rain and cold temperatures, or trip was fun. Lunch at an organic wine farm was delicious.
Review provided by Viator
Fay_b
May 5, 2024
Wonderful day !! - We had a wonderful day ! Beautiful countryside and excellent lunch, the wine was amazing- would highly recommend this experience!
Review provided by Viator
Jeffrey_l
Apr 29, 2024
Rainy but very enjoyable - This was an amazing tour. Stephano was our driver/guide. He was very personable and definitely made the trip one to remember It rained most of the day but we were able to make the best of it. San gimignano was amazing and wish there was a little more time there. The winery was limited due to weather but the staff did a great job and we still had a great experience. Plenty of wine. Siena was great and our guide was very informative and accommodating for a member of our group that wasn’t a little slow moving that day. I can’t recall her name, I apologize. I highly recommend this tour.
Review provided by Viator
Nigelf60
Jun 9, 2024
An excellent Day out - The guide meets you at the main railway station , close to the taxi rank, and McDonalds is on the opposite side of the rad, and a small kiosk selling refreshments etc, very close to meeting point. From the meeting point there is a 10 min walk to where the coach is parked. The day started at 0800 hrs, and finished at 2100hrs. The sites visited were very interesting, lunch was excellent at the winery, with excellent toilet facilities, and a shop that sells their wines. etc. The high light was the "Church/Cathedral) at Sienna is stunning and beautiful.. We were so pleased we booked the tour as we saw so much more and understood so much more than trying to do it alone. Stefano the guide was excellent, so knowledgeable, helpful and patient and funny. Thank you
Review provided by Tripadvisor
From $588
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).