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 tour was fantastic! Would definitely do it again!
Schirin was an excellent tour guide and helped make our Tuscany day trip one of the highlights of our visit to Italy. She was knowledgeable, friendly, organized, and provided great recommendations at each stop along the way. We especially appreciated her approach to guiding the tour. Rather than overwhelming us with information, she gave us useful background on each destination, pointed out the highlights, suggested places to visit, and then allowed us enough free time to explore on our own. The small-group format and comfortable mini-bus made the experience much more enjoyable than traveling on a large tour bus. The medieval towns we visited were beautiful and full of character, and the Tuscany wine tasting was outstanding. The winery experience was well organized, the wines were excellent, and it was a wonderful way to experience the region. The only minor issue was that the tour took place on a Sunday. A few of the shops and attractions Sharon recommended were either closed or opened later than expected, which unfortunately prevented us from enjoying some of her suggestions. This was a relatively small inconvenience and may have been due to changing local business hours rather than anything within her control. Overall, Schirin did a fantastic job, and we would highly recommend both her and this tour to anyone looking to experience Tuscany and its charming medieval towns. The combination of beautiful scenery, great wine, a comfortable small-group experience, and an excellent guide made for a memorable day.
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.
