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 6 wine tastings
Free CancellationDay Trip
4.94
(210)
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
210 Ratings
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Great Day Trip
Jill Fukumoto
Verified Review
June 03, 2025
This day trip was a lot of fun! Loved Siena and San Gimignano. Both towns were so cute…only wish I had more time there. The winery was amazing. Beautiful vineyard and lunch was delicious. The wine/balsamic vinegar/olive oil were also fantastic. Ended up having a box shipped home! Overall really great experience and our tour guide Frederica was super nice and knowledgeable.
Roger Athey
Verified Review
June 03, 2025
Linda Luna Lara
Verified Review
June 03, 2025
Ronald Kudo
Verified Review
June 02, 2025
Florence day trip
Colby Carlson
Verified Review
June 02, 2025
Fantastic tour with an excellent guide and driver
Great day trip
Marc Krigsman
Verified Review
June 02, 2025
We really liked our day trip, and the guide was great too. It was a seamless and enjoyable way to visit 3 Tuscan cities without the chore of navigating public transportation. The lunch exceeded expectations with the full wine tasting, and the addition of balsamic vinegar tastings. Would recommend.
Abdoul Diallo
Verified Review
June 01, 2025
Linda Anderson
Verified Review
May 30, 2025
Beautiful Day!!
Stephen Balistreri
Verified Review
May 28, 2025
The drive through Tuscany was absolutely beautiful and it was great to be able to see Siena and San Gimignano. Our tour guide, Fredericka was amazing. She gave us some history before escorting us into the cities and then gave us a lot of free time to roam around ourselves. What a great experience! The winery was great too! We were greeted by our host who gave us some history of the vineyard and then we went into a private room where we had wine and food pairings (both of which were delicious). Our driver Nico was very skilled! We felt very safe in his hands. Thank you to Fredericka, Nico and our host at the winery for making this a great day!
Mark Amendola
Verified Review
May 28, 2025
Gwen Hagenbarth
Verified Review
May 26, 2025
Florence Day Trip
Rodney Pagila
Verified Review
May 26, 2025
Awesome time
Stuart Cowitt
Verified Review
May 26, 2025
Great day in Tuscany
Nancy Pollak
Verified Review
May 24, 2025
Really enjoyed the day but wish we had more time in the towns. The winery was a wonderful experience- both wine and food. Our guide, Frederica, was knowledgeable and friendly and kept us on schedule
Wonderful Wine tasting, Tuscan tour
Thomas Acosta
Verified Review
May 24, 2025
We enjoyed a totally delightful tour of Siena, San Gimignano and wine tasting and lunch at a Tuscan winery!
Wendy MacLean
Verified Review
May 23, 2025
Tuscany Tour
Donald M Browning
Verified Review
May 23, 2025
We enjoyed the tour, visiting Italys Tuscany countryside, several different towns and great wine tasting and excellent lunch!
Laila was a great host and shared a lot of great history and insight about the region.
Would definitely recommend.
Good tour
Sunanda Narayanan
Verified Review
May 21, 2025
This is an excellent and quick way to see the Tuscan region. The lunch at the winery was superb and the presentation was good, but it was a hard sell on the products that seemed to be quite overpriced as well. If that aspect of the tour could be toned down, it would make for a perfect day trip.
Siena, San Gimignano & Winery Lunch
Catharine Larocque
Verified Review
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.