Tuscany Wine Tour from Florence to Siena & Chianti
Enjoy a luxury Tuscany day trip to visit Siena and San Gimignano then taste food and wine in Chianti
Planning a day in Tuscany’s countryside can be tricky, with winding roads, remote villages, and countless wineries to choose from. We take the guesswork out of the experience by starting in Florence and guiding you through Siena’s rolling hills, the medieval streets of San Gimignano, and celebrated Chianti wineries. Along the way, learn the stories behind Chianti’s renowned wines and soak in the charm of Tuscany’s most stunning landscapes. It’s the ideal way to savor Tuscany without the hassle.
- Meeting point at Viale Filippo Strozzi
- Meet your tour leader
- Hills of Tuscany
- Siena
- Free time for Cathedral visit
- Chianti Winery
- Lunch and wine tasting
- San Gimignano
- Free time in San Gimignano
- End at Viale Filippo Strozzi
Meet your tour leader in Florence at Viale Filippo Strozzi 1, and hop aboard your luxury, climate-controlled vehicle with no more than 15 other travelers. 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 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.
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
Traditional Tuscan lunch
Visit the picturesque medieval town of San Gimignano
An English-speaking tour leader for the day
Maximum group size of 15
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
Continue your journey through the Chianti hills and olive groves, before arriving at a traditional family-run farm and winery. You'll learn from the locals about famous grapes and the winemaking process from vine to bottle, before sampling them yourself!
Then sit down for a delicious lunch made from locally grown ingredients from the farm, staying true to the Italian slow food movement and traditions of Tuscan cuisine. Lunch and wine are included, and it's easy to order a few extra bottles to take home with you too!
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.
What you get with this tour
See what people are saying
148 total reviews
Leave a reviewAlexandra McCarron
Jennifer Gaston
Amazing tour
Jennifer Duest
Great tour and perfect length of time.
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 15 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!
How much free time do you have in Siena?
You'll have about 2 hours of free time in Siena.
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