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

Passionate English-speaking host
Transportation
Winery tour
Tuscan lunch
Siena
San Gimignano
Wine tasting
Free time
Max 31 people
Tour guide gratuities
Hotel pick up

Tour Itinerary

1

Meeting point at Piazzale Montelungo
Exact location can be found on your voucher.
2

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!
3

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
4

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
5

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!
6

Chianti Winery
Learn about the process of winemaking at a family-run winery and farm, followed by a tasting of their delicious vino!
7

Lunch and wine tasting
Enjoy a decadent lunch made from the farm’s locally grown produce, and pair your wonderful meal with the estate’s very own wine!
8

San Gimignano
Take a step back in time as you explore the narrow streets of San Gimignano, a medieval town famous for its skyline of ancient towers
9

Free time in San Gimignano
Enjoy free time to see San Gimignano’s top sights, including the historic Piazza della Cisterna and a medieval church from the 12th century!
10

End at Piazzale Montelungo
Sit back and enjoy the ride as you’re driven back to your original meeting point in Florence’s city center

Additional Information

Meet your tour leader in Florence at Piazzale Montelungo, 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 beautiful old towns of San Gimignano and Siena, and enjoy a hearty, delicious lunch in Chianti. Your tour will conclude at Fortezza Piazzale Montelungo, near the Santa Maria Novella train station.

Tuscany Wine and Food Tour Description

Your 9-hour day trip from Florence includes:

Round-trip transportation from Florence in a climate-controlled vehicle
Visit beautiful 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 picturesque medieval town of San Gimignano
An English-speaking tour leader for the day
Maximum group size of 29

Historic Siena

Your first stop on this Tuscany day trip is the famous city of Siena. Twice a year, the city holds the famous Palio horse race that has been run since the Middle Ages in Siena's central square, Piazza del Campo. Along with your knowledgeable tour leader, you'll see this famous square and the oldest bank in the world. After getting oriented in Siena, you'll have some free time to explore, and we recommend purchasing a ticket to visit the Siena Cathedral on your own.

Chianti Winery for Lunch and Wine Tasting

At a family-run winery that has been perfecting Tuscan wine for 13 generations, enjoy a private tour of their vineyards, wine cellar, and fermentation cellar before indulging in a curated tasting of their finest products. Sip on a selection that includes Vernaccia di San Gimignano DOCG, Rosé, Chianti, Super Tuscan Riserva, and Morellino di Scansano, paired with artisanal olive oils like extra virgin, truffle, and spicy pepper, as well as their Gold Reserve balsamic vinegar.

The lunch is a true Tuscan feast. Start with appetizers of Tuscan cheeses, cured meats, bruschetta, and salad. Savor the first course of Lasagne al Tartufo and hearty Tuscan ribollita, followed by dessert: cantucci paired with Vin Santo. This exceptional dining experience highlights the rich flavors and heritage of Tuscany, making your visit unforgettable.

Medieval San Gimignano

The next stop on your Tuscan journey is an incredible little town, sometimes nicknamed “Medieval Manhattan.” As a UNESCO World Heritage site that feels straight out of a fairy tale, San Gimignano is known for the towers that create its iconic skyline, bringing to mind modern day skyscrapers. Once inside the city walls, enjoy some free time to explore this remarkable and historic town.

Return to Florence

After an idyllic day visiting historic Tuscany cities and enjoying the food and wine of Chianti, it's time to head back to Florence. Simply sit back and relax as your professional driver takes you safely back to the city.

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4.9/5 (based on 244 reviews)

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1 stars

31 October 2025

Reviewed by
Luisa Mesa

Review

26 October 2025

Reviewed by
Gurmeat Uppal

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.!

25 October 2025

Reviewed by
Nancy Fendler

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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!