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
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.
What You Get With This Tour
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Expert, English-speaking guide
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Round-trip transport
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Guided winery tour in Chianti
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Tasting of 6 wines
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Traditional 3-course Tuscan lunch
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Artisanal olive oil and balsamic tasting
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Guide tips
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Siena Cathedral entry ticket
Tour Itinerary
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1
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. -
2
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. -
3
Chianti winery tour and 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. -
4
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 paired with Vin Santo for a true taste of Tuscany's culinary heritage. -
5
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. -
6
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.
Additional Information
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.
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.
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 9-hour day trip from Florence 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
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)
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Customer Reviews
This was a wonderful tour, Fredrica was absolutely wonderful, she keep us well informed and everybody on schedule.
Enjoyed the tour; especially the winery. The lunch was delicious too! Wish there was more time in each town though but overall it was very enjoyable.
5-star trip because the tour guide is a 5-star guide, which we also experienced last year in our Firenze food trip.
My mother and I had a great time. The guide, Federica, was terrific and very sweet. Our driver was also great! The scenes were beautiful and the winery was fantastic. 5 stars all around.
Amazing experience to Celebrate my 53rd birthday! Great time!!!
Frequently Asked Questions
I'd prefer a private day trip to Chianti. Can this be arranged?
Yes, we offer a similar private day trip from Florence with private transportation and pickup/drop-off at your Florence accommodation. Check out our Private Wine Day in the Chianti Hills From Florence
Is a guide included on this day trip?
No, you'll be accompanied by a friendly and knowledgeable trip leader and a driver the entire day, but at most stops you'll be free to explore by yourself after getting oriented at each stop.
Are lunch and wine included in the price of this day trip?
Yes, it's all included in the tour price.
What if I want to see Chianti and San Gimignano but I don't drink alcohol?
You are still welcome to join the tour, as alternate drinks can be provided during the lunch and wine tasting. Please contact us to let us know your prferences.
Are children allowed to join this tour?
Yes! Children under 6 are permitted on this tour for a discounted price.
Does this include a guided tour of the Siena Cathedral?
This tour does not include a guided tour of the Siena Cathedral. As you have free time in Siena, we recommend buying entry tickets in advance in order to enter!
How much free time do you have in Siena?
You'll have about 2 hours of free time in Siena.
