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 (244) ·

Travel Flexibly

· 9.00h · Florence, Italy

Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch

A group of tourists having their picture taken while on a vineyard in Tuscany.

A tourist meeting their tour guide before entering a van with The Tour Guy.

A couple of tourists viewing the Terra Mater statue in Siena while on tour with The Tour Guy.

A group of tourists walking through Siena while on tour with The Tour Guy.

A couple of tourists walking through a vineyard while on tour with The Tour Guy.

A group of tourists sitting at a table and receving their lunch while on tour with The Tour Guy.

An image of fresh pasta and a flight of Tuscan wines.

A tourist dipping a biscotti into a glass of wine while on tour with The Tour Guy.

A couple of tourists sitting on a wall in San Gimignano, Italy.

A group of tourists having their photo taken outside of Piazza della Cisterna in San Gimignano while on tour with The Tour Guy.

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

Expert, English-speaking guide
Round-trip transport
Guided winery tour in Chianti
Tasting of 6 wines
Traditional 3-course Tuscan lunch
Artisanal olive oil and balsamic tasting
Guide tips
Siena Cathedral entry ticket

Tour Itinerary

1

Your tour begins at Piazzale Montelungo
Meet your tour leader at Piazzale Montelungo in Florence and board a comfortable, air-conditioned vehicle. You'll embark on a scenic journey through Italy's most famous food and wine region with a passionate local guide and private driver.
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 at Piazzale Montelungo
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, concluding at Fortezza Piazzale Montelungo near Santa Maria Novella train station.

Additional Information

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
Maximum group size of 29

What to bring:

Comfortable walking shoes
Water bottle
Sunscreen (in the summertime)
Government-issued ID (if you plan to partake in alcohol)

Customer Reviews

4.94 (244)

Leave a review

Luisa M., 31 October 2025

Review

Gurmeat U., 26 October 2025

Great assistance by Lori and helped us in getting taxi beyond her work time. We felt proud of such Italian hospitality!! The whole trip has etched in our memory for life.!

Nancy F., 25 October 2025

Michael B., 24 October 2025

Fun day

Julie B., 17 October 2025

This was a great tour to see the Tuscany area. The wine tasting was more of a sales pitch. Would have been nice to have more Siena info.

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Frequently Asked Questions

What to bring?

Bring sunscreen in the summertime and a bottle of water. You'll also want comfortable walking shoes to wander the towns and vineyards.

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 this a private day trip?

No, this is a small-group tour so you'll enjoy the day with just 29 or fewer passengers.

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.

What to bring?

Bring sunscreen in the summertime and a bottle of water. You'll also want comfortable walking shoes to wander the towns and vineyards.

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!