from
$92
From Florence: Tuscany Day Trip with Siena, San Gimignano & Winery Lunch
Relax on this Tuscan day trip with a 3-course lunch and 6 wine tastings
What's included
English-speaking tour leader
Round-trip transportation from Florence
Visit Siena with free time
Guided winery tour in Chianti
Taste 6 different wines
Traditional 3-course Tuscan lunch
Artisanal olive oil and balsamic tasting
Visit medieval San Gimignano
Guide tips
Siena Cathedral entry ticket
Itinerary
Transportation included
Meet your guide at Piazzale Montelungo
Your tour begins in central Florence
Meet your tour leader in central Florence (look for the exact location on your booking voucher). Here, you’ll board a comfortable, air-conditioned vehicle and embark on a scenic journey through Italy's most famous food and wine region.
Make a stop in historic Siena
Your first stop is the beautiful city of Siena, home to the famous Palio horse race held in the central Piazza del Campo since the Middle Ages. You'll explore this iconic square and see the world's oldest bank with your guide. Afterward, enjoy free time to wander the city and visit the stunning Siena Cathedral on your own.
Take a Chianti winery tour and enjoy a tasting
Next, visit a family-run winery that has perfected Tuscan wine for 13 generations. You'll tour their vineyards, wine cellar, and fermentation areas before enjoying a curated tasting of six wines, including Vernaccia di San Gimignano DOCG, Rosé, Chianti, Super Tuscan Riserva, and Morellino di Scansano, paired with artisanal olive oils and Gold Reserve balsamic vinegar.
Indulge in a traditional Tuscan lunch
Savor a three-course feast featuring Tuscan cheeses, cured meats, bruschetta, and salad, followed by Lasagne al Tartufo and hearty ribollita. Finish with cantucci, almond biscotti, paired with Vin Santo dessert wine for a true taste of Tuscany's culinary heritage.
Explore medieval San Gimignano
After lunch, explore San Gimignano, a UNESCO World Heritage site nicknamed "Medieval Manhattan" for its iconic tower skyline. You'll have free time to wander inside the city walls and discover this fairy-tale town.
Your tour finishes in central Florence
After a wonderful day exploring historic Tuscan cities and savoring the region's food and wine, relax as your driver takes you back to Florence. The exact ending point can be found on your booking voucher.
For Reference Only. Itineraries are subject to change
Select participants and date
Start times are in the product’s local time
Free cancellation up to 24 hours in advance!
Fri, 23 Oct 2026
Meeting and drop-off point
Important Details
Discover what to expect, what's included, and everything you need to know before booking.
Good to know:
Dress Code: Comfortable walking shoes are essential for exploring the medieval towns and vineyards on this tour. Please note that if you plan to visit Siena Cathedral during your free time, they do require both men and women to have their shoulders and knees covered for entry.
Accessibility: Unfortunately, this tour is not wheelchair accessible due to the vehicle specifications and uneven terrain.
Dietary Restrictions: This tour includes a traditional 3-course Tuscan lunch with wine; please contact us with any dietary needs in advance so we can do our best to accommodate.
Please Note: Car seats are available upon request which must be made at least 72 hours in advance.
Alcohol Consumption: This tour includes wine tastings; participants consuming alcohol should be of legal drinking age in Italy (18).
Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can enter sites on time.
Your day trip includes:
English-speaking tour leader for the day
Round-trip transportation from Florence in a climate-controlled vehicle
Visit Siena with free time to visit the cathedral (on your own)
Wine tour and tasting at a traditional, family-run winery in Chianti
Taste 6 different wines
Traditional 3-course Tuscan lunch
Artisanal olive oil and balsamic tasting
Visit the medieval town of San Gimignano
What to bring:
Comfortable walking shoes
Water bottle
Sunscreen (in the summertime)
Government-issued ID (if you plan to partake in alcohol)
See what people are saying
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310 verified ratings
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What reviewers sayPowered by Cicero AIBETA
Reviewers frequently praise the knowledgeable and friendly guides and drivers who provide informative and enjoyable experiences in Tuscany. Many highlight the beautiful towns of Siena and San Gimignano, the excellent wine tastings, and the delicious lunches at family-run wineries, though some found the time in towns a bit short and the winery tours less detailed than expected.
Great Tour with Victoria
Casey G.
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October 20, 2026
Victoria made the tour!
Great experience
Dian A.
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October 20, 2026
We loved this kind of tour, no rushing no pressure, Frederika also very helpfull and such a pro guide
Siena, San Gimignano and wine tasting
Wendy L.
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October 19, 2026
We had a really lovely trip - Highly recommend
Siena, San Gimignano & Winery Lunch
James H.
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October 17, 2026
I had a wonderful time on this tour with a great tour leader who kept things upbeat, and interesting the whole time.
Siena San gimignano
James H.
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October 17, 2026
Great tour, great tour guide
Rebecca C.
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October 16, 2026
Siena, San Gimignano, Pisa and Tuscan Lunch & Wine Tasting
Kristen H.
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October 09, 2026
Everything was great. The bus, bus driver, and our tour guide Mano.
Great Tour
Cindy V.
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October 09, 2026
We really enoyed this tour. The staff was very friendly. It was great to get out of the crowds of Florence. Suggest getting a knowledge of Siena and San Gimignano before you go. We had ChatGPT create a walking tour for us so we can see the highlights.
Fantastic experience
Yaneth L.
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October 05, 2026
The staff was very kind and we had a great time
Hal R.
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October 02, 2026
Take the day trip, it's lovely!
Janet W.
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October 01, 2026
Fiama was an excellent guide. She was so sweet, accommodating and knowledgeable. She managed our group very well, which it is hard to herd people sometimes. The history of the wine in the region is so interesting. Salute Fiama! Behar was an excellent driver. So nice to have someone else do all the work so we can relax.
Great Tuscan day tout
Willam R.
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October 01, 2026
The was great. Got to really see and experience the Tuscany region. Our tour guide was exceptional as was the bus driver. We were given ample free time in each of our stops. Highly recommend doing this day.
Stephen B.
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September 28, 2026
We had a great tour, mostly thanks to our excellent guide, Christiana, and our driver Allesandro.
We learned a lot and had fun!
Renee Z.
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September 25, 2026
It was a fun day with a great guide. Lunch and wine were great! The best balsamic vinegar ever!!
Great Tuscany Wine Experience
MELODY M.
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September 23, 2026
This tour was wonderful and our tour guide Fabi was really good! Loved the visits to Siena and San Gimignano, they were better than expected. The winery tour was amazing. I learned a lot and of course enjoyed the wine.
Karen G.
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September 21, 2026
Great Tour
David G.
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September 20, 2026
Great day trip
Tyler M.
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September 18, 2026
We had a great time seeing the countryside. Fiamme was a wonderful guide.
Vijay P.
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September 14, 2026
Michelle S.
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September 07, 2026
Great tour! Winery lunch was amazing & visits to the towns were perfect. Thank you to our guide Frank (Frankgelica??)
Great day trip !
Andrew F.
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September 05, 2026
Well worth doing, great combination of sight seeing and winery lunch !
Very well planned tour
Deepak M.
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September 03, 2026
Our guide Fabi was extremely nice and accommodating. The tour was fantastic and covered everything they mentioned in the itinerary. The winery was really good with loads of good wines for tasting. So we came for the wine but ended up loving the olive oil and buying those! Highly recommend this!
Wonderful day spent touring Tuscany
Megan B.
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September 03, 2026
Our tour guide, Francesca, was wonderful providing a great balance between education and free time. She was friendly, patient, and informative. My family of 4 thoroughly enjoyed our day & definitely have no regrets about booking this particular tour. Alessandro was a great driver for our group also.
Brittan C.
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August 28, 2026
Nancy
Nancy C.
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August 24, 2026
Our tour was fantastic, our tour guide, Scirin Agha was a lot of fun and very informative. The lunch and wine tasting was delicious. A very smooth and enjoyable day!
FAQs
I'd prefer a private day trip to Chianti. Can this be arranged?
I'd prefer a private day trip to Chianti. Can this be arranged?
Is a guide included on this day trip?
Is a guide included on this day trip?
Are lunch and wine included in the price of this day trip?
Are lunch and wine included in the price of this day trip?
What if I want to see Chianti and San Gimignano but I don't drink alcohol?
What if I want to see Chianti and San Gimignano but I don't drink alcohol?
Where to meet?
Where to meet?
Are children allowed to join this tour?
Are children allowed to join this tour?
Does this include a guided tour of the Siena Cathedral?
Does this include a guided tour of the Siena Cathedral?
How much free time do you have in Siena?
How much free time do you have in Siena?
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