Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch
Free CancellationDay Trip
Relax on this Tuscan day trip with a 3-course lunch and 5 wine tastings
4.94
(163)
9 h
Max 29 Guests
Planning a day in Tuscany’s countryside can be tricky, with winding roads, remote villages, and countless wineries to choose from. With a 3-course lunch and 5 wine tastings, allow us to take the guesswork out of your Tuscan experience. Start in Florence, drive through Siena’s rolling hills, walk the medieval streets of San Gimignano, and tour a family-run Chianti winery. Along the way, learn the stories behind Chianti’s renowned wines and soak in the charm of Tuscany’s most stunning landscapes.
Meet your tour leader in Florence at Piazza del Duomo 10, and hop aboard your luxury, climate-controlled vehicle. You'll enjoy an entertaining ride from Florence through the most famous food and wine region in Italy, accompanied by a passionate local tour leader and private driver. Tuscany awaits to share its bounty of gorgeous foods and wines, and you'll meet the local people who can show you wine-making techniques passed down through 13 generations. You'll also get to explore the insanely b...
Select participants and date
Free cancellation up to 24 hours in advance!
Travelers
Passionate English-speaking host
Transportation
Winery tour
Tuscan lunch
Siena
San Gimignano
Wine tasting
Free time
Group size of 29
Tour guide gratuities
Hotel pick up
Wheelchair accessible
Meeting point at Piazza del Duomo
Head to Piazza del Duomo, centrally located in Florence’s city center and the starting point for your Tuscan adventure!
Meet your tour leader
After meeting your friendly tour guide and private driver, you’ll hop into your luxury vehicle for the day and be whisked away in style!
Hills of Tuscany
Take in the sights of idyllic olive groves and picturesque vineyards as you’re driven through the rolling green hills of Tuscany
Siena
Explore the famous Piazza del Campo and pay a visit to the world’s oldest bank as you wander through one of Tuscany’s most enchanting cities
Free time for Cathedral visit
As you enjoy free time to explore Siena on your own, be sure to visit the city’s medieval church, which dates back to 1215!
For Reference Only. Itineraries are subject to change
Meet your guide at Piazza del Duomo 10 in front of the small fortress. A friendly representative will be there holding a sign with our company name on it.
Bring sunscreen in the summertime and a bottle of water. You'll also want comfortable walking shoes to wander the towns and vineyards.
4.94
163 Ratings
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Super fun day
Nola Palmer
Verified Review
April 17, 2025
Anna was a fantastic guide!!
Jackie Bracke
Jackie Bracke
Verified Review
April 13, 2025
We had a great day. Our guide was great and knowledgable and very happy to help with anything. Siena was lovely - shame we had such a short time there - it felt quite rushed.
The winery was beautiful with gorgeous food and brilliant hosts. I did feel the video of the trip was a bit misleading tho. It wasn’t the same winery as the one we were taken too - and it seemed a real shame to shut in a room indoors on such a beautiful day , when they had such lovely outdoor spaces. The video also shows the lunch to be outside .
San Gimignano was amazing - my favourite part of the trip and we had a nice long time there as well .
Overall a great trip- just a shame we couldnt absorb the outdoor atmosphere at the winery .
Andrea Chen
Verified Review
April 11, 2025
Jennifer Loftus
Verified Review
April 11, 2025
Michelle Watkins
Verified Review
April 08, 2025
Nancy McDermott
Verified Review
April 07, 2025
Fabulous!
Gillian Grose
Verified Review
April 07, 2025
Although travelling in two cars wasn’t ideal, the guide did his best to keep us informed about the highlights of each place. Lunch at the winery was exceptional! Highly recommended.
Jan Hurley
Verified Review
April 07, 2025
Brian E. Morey
Verified Review
April 05, 2025
Wonderful introduction to Tuscany
Sheela Kennedy
Verified Review
April 02, 2025
We enjoyed our tour with Anna. She is very knowledgeable and fun to spend a day with. My only regret is that we didn’t buy the balsamic at the winery. Highly recommend.
Loved this tour
Debra Mendoza
Verified Review
April 01, 2025
I loved everything about this tour. Beautiful scenery, knowledgeable guide and amazing food and wine. Would highly recommend.
Jeannine Grasso
Verified Review
March 22, 2025
Roopashree Jeevaji
Verified Review
December 22, 2024
Amazing tour !! Francesco was very engaging, friendly and provided a lot of information .
Samantha Osby
Verified Review
December 08, 2024
Lisa Grant
Verified Review
December 05, 2024
Alexandra McCarron
Verified Review
December 03, 2024
Jennifer Gaston
Verified Review
November 19, 2024
Amazing tour
Jennifer Duest
Verified Review
November 12, 2024
Great tour and perfect length of time.
A Wonderful Experience!!!
John Cheeseman
Verified Review
October 13, 2024
This tour was perhaps the best of our whole trip. Our guide, Marco, made it a special experience! For me. San Gimignano was the wild card. We really didn't know what to expect, but I can tell you that it was beautiful. There is a lot packed into this experience, but we loved it!!!
Fabulous Day in Tuscany
Nancy Finckenor
Verified Review
October 08, 2024
We had such an informative, fun, and well paced day with our guide Frederica! We were able to enjoy free time in Siena and San Gimignano to explore , take pictures and shop. She also informed us of the history of the towns. The family owned winery tour , tasting and lunch was educational and delicious. The whole day was unforgettable and relaxing. We would definitely recommend this tour.
Fabulous Day Out in Tuscany
Tony McNally
Verified Review
October 06, 2024
The most enjoyable day with a great tour lead Fredi
We had an awesome tour and tour guide !
Lesley Vullo
Verified Review
October 03, 2024
The trip was wonderful and Lori our guide was very knowledgeable and super friendly!! We enjoyed everything as well as Claudia our driver ! We were sad to leave after .
Heather Gauthier
Verified Review
October 03, 2024
Alice took us on a lovely trip to Siena, a winery, and San Gimignano
Karam Basra
Verified Review
September 25, 2024
Alice did an excellent job leading us through Siena and San Gimignano and then letting us roam and explore on our own. As she explained from the beginning, she was there to shepherd us from one site to the next more than give us an in-depth tour every moment of the day. We enjoyed our wine tasting and small bites at the winery too. By the way, two of our group mates misunderstood the instructions about the meeting place when we were in Siena and after we waited awhile for them they had to be left behind and luckily they got to the winery on their own. I want Alice's bosses to know she was clear, the tourists messed up, and she handled an awkward situation with grace even when the group mates took no responsibility for their own screw-up.