Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch
Relax on this Tuscan day trip with a 3-course lunch and 6 wine tastings
4.94
(191)
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!
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
191 Ratings
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Siena, San Gimignano & Winery Lunch
Catharine Larocque
May 20, 2025
We had a lovely day. The visit to the towns was a little rushed. We had one hour for each and the bus parked quite a piece away from Siena cutting into that time. The winery lunch was delicious. No winery tour or visit to vineyard. Close to the main highway. We turned off and down one road and the tour guide said, “now we are in the middle of nowhere.” I didn’t get that feeling. Wish we had more time to drive around countryside.
Matthew Regan
May 15, 2025
Bruce Anderson
May 15, 2025
Sunanda Narayanan
May 14, 2025
Mary Chappell
May 14, 2025
Jennifer Conway
May 12, 2025
sonali reddy
May 12, 2025
Great tour!!!
Renae Krivitz
May 08, 2025
We had a wonderful tour with Anna yesterday. She was so friendly & accommodating throughout the whole day. We would recommend this tour!
George Justice
May 07, 2025
Geojoe Kuruvila
May 06, 2025
Great Tour for several reasons
Richard Kimball
May 06, 2025
Our tour guide Ana did a great job from start to finish. She was very good at explaining what we were doing on each event but also had great personality while conducting our tours. The tours to Siena, San gimignano and Poggio AI Laghi Winery were amazing.
Amy Friedner
May 05, 2025
Cute Towns and a Fun Lunch w/ Great Wine
Joseph Quinn
May 04, 2025
Overall a great day. The size of the group was great - not as big as so many I see around Rome and Florence. The two towns chosen for walking around are super cute. That said, I wish I would have known the extensive artwork living in the Siena Cathedral are not in the main cathedral, but are in the Museum, the Crypt, the Baptistery, etc and there is not enough time during the tour to see them. The countryside views are beautiful. The time in the bus is not bad at all. And the lunch and wine tasting were great although there was really. not much of a winery tour - we simply walked through the building, heard the basics of the history / naming of the wines and then went to the table to eat and drink. No tour of the vineyard, the bottling, the barreling - that part could have had more detail and information. But the tasting and lunch were great!!! I would recommend this tour to a friend.
Fun day trip from Florence
Jeanette Haas
May 03, 2025
This tour was a fun and easy day trip to get out of Florence and see some of Tuscany. The group was friendly and the bus was very nice. Seeing the Tuscan countryside from the coach was great. The journey is not too long. The towns were amazing, although still crowded like Florence. The time is quite short in each stop. The winery lunch was really enjoyable. Our tour guide, Francesco was awesome and very fun. He had lots of tips.
For Lorenzo. Tuscany Tour
Suzanne Zsikla
May 03, 2025
We had a fantastic day on the Tuscany tour with Lorenzo! He was fun, knowledgeable and fully involved with all of the tourists…..will definitely refer Lorenzo and The Tour Guy company to our friends and family. Suzanne
Wine Tour
Anjela Bavaro
May 03, 2025
Amazing day with Lorenzo!!! Enjoyed every minute!!!
Excellent Tuscany Tour
Michele Conner
May 03, 2025
Our Tuscany tour was one of the most excellent experiences of our Italy trip. Sarah, our guide was friendly and very knowledgeable about the Tuscany/Florence region and history. Our driver Rick, was also exceptional and very friendly as well. We enjoyed the Tuscan countryside, Siena and San Gimigiano so much! The lunch and wine tasting was truly outstanding! OVERALL.....10 stars out of 5 Thank you once again!!! Michele Conner and Karen Roberson
Earl Roberts
May 03, 2025
Rebecca Collier
May 02, 2025
Charles DeMola
May 01, 2025
Great Mix of Wine Tasting and Old World Town Tour
April Horton
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
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
April 28, 2025
Lee Charouhas
April 27, 2025
Blown away
Michael Giordano
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.