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
(172)
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 6 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
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
172 Ratings
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Charles DeMola
Verified Review
May 01, 2025
Great Mix of Wine Tasting and Old World Town Tour
April Horton
Verified Review
May 01, 2025
Mani & Richard did a great job informing and keeping us safe on the tour. The schedule was just right, lots of great scenery!
Great Tour
Frank Zissis
Verified Review
April 29, 2025
We loved this tour! Siena and San Gimignano are absolutely beautiful. The winery tour was great and very informative. We learned a lot about wine and enjoyed tasting many different kinds of wine. The lunch at the winery was delicious!
Vince Rudinica
Verified Review
April 28, 2025
Lee Charouhas
Verified Review
April 27, 2025
Blown away
Michael Giordano
Verified Review
April 27, 2025
The winery we went to, Torciano Winery, just blew away all expectations of my travel party. The grounds were amazing. Upon our arrival, another group had paid to test drive about ten different Ferraris and Porches, so seeing (and hearing) that was pretty cool. The wine was fantastic— no headache afterward, and the food was just as good. I was expecting a few meats and cheeses, but it was a full Tuscan meal. Siena and San Gimignano were both beautiful. You get about an hour in both places. Just enough to skim the surface. The bus was clean and plush. We HIGHLY recommend this tour. A thanks to Anna our guide and Pietro and Lorenzo from the winery. Fantastic experience. Wife and I purchased a case of 12 (assortment), we liked the wine that much.
Krista O'Donnell
Verified Review
April 21, 2025
meg schnabel
Verified Review
April 21, 2025
Incredible tour
Yvonne Marshall
Verified Review
April 19, 2025
We had such a wonderful time on the Florence Day trip to Tuscany. Our guide Frederica was so friendly and patient with this group of 24. Our driver Murcio (?) was incredibly skilled, maneuvering the bus in tight spaces, and getting us there & back, safe & sound!
We learned so much at the Vineyard! The wine was excellent but the food was equally mind-blowing! I highly recommend this tour!
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 .