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

Travel Flexibly 4.9 / 5 See All 115 Reviews · 9.00h · Florence, Italy

Looking for a simple way to explore Tuscany from Florence? Want to visit an iconic winery in Chianti and take in those epic views in San Gimignano? Then you've found the perfect tour! Sit back and relax on this small group food and wine adventure through the Tuscan countryside. You'll see the farms and vineyards that make the region’s famous cuisine and delectable wines. Learn the secrets of Chianti wine and watch local life unfold in tiny medieval villages that have barely changed in centuries.

  • Transportation included
  • 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
Passionate English-speaking host
Transportation
Winery tour
Tuscan lunch
Siena
San Gimignano
Wine tasting
Free time
Group size of 15
Tour guide gratuities
Hotel pick up
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See what people are saying

115 total reviews

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4.9/5 (based on 115 reviews)
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Very enjoyable tour!
08 June 2024
R
Reviewed by
Ronald Frank

Well organized and enjoyable tour! Anna, our guide, was knowledgeable, friendly and constantly ready to go the extra mile to help us! Ivan, our driver was always on time and knew the roads well. The stops were well chosen, including the winery. Great way to experience the Tuscan countryside!

08 June 2024
R
Reviewed by
Ronald Frank

Wonderful!
03 June 2024
H
Reviewed by
Helen Grant

We thoroughly enjoyed this tour and would recommend to anyone. Our tour guide was great. Just the right amount of information and was very knowledgeable. Liked that we travelled in two small comfortable vans - total of 13 people in our tour. The time in the towns of Siena and San Gimignano let you explore on your own after a brief guided tour, which I appreciated. The wine tour, tasting and lunch was wonderful. Our favorite part of the trip. I had read in prior reviews that the lunch servings were too small but I don’t agree. When you stop in Siena it is famous for its pastries and so our family took the tour guides advice and stopped for coffee and a pastry. This was followed by the lunch at the winery and then in our stop in San Gimignano which is known for its world famous gelato - we of course could not resist and it was fabulous. Make sure to find the panoramic view from the back of San Gimignano - it is breathtaking. We sat at a little restaurant and enjoyed a glass of wine while soaking in the view before heading back to Florence. We enjoyed this trip so much that I have searched for other tours with the Tour Guy. Thank you all for a great day!

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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 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.

Start From: $162.35

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$162.35 / per person
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