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 56 Reviews · 9.00h 18 max · 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, wineries, and vineyards that make the region’s cuisine so famous. Learn the secrets of Chianti wine and watch local life unfold in tiny medieval villages that have barely changed in centuries.

  • A memorable day in the countryside
  • Luxury transportation from Florence
  • Rolling hills of Tuscany
  • Historic Siena
  • Siena Cathedral
  • Explore the Chianti region
  • Traditional farm and winery
  • Tuscan cuisine for lunch
  • San Gimignano
  • Transportation back to Florence

Meet your trip 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 trip 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 luxury, climate-controlled vehicle

  • Visit beautiful Siena, with free time to see the Cathedral of Siena

  • 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 trip 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 trip leader, you'll see this famous square and have free time to explore the beautiful Cathedral of Siena, plus the oldest bank in the world!

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.” 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. 

Chianti Region 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
Round-trip transportation from Florence in luxury, climate-controlled vehicle
Visit beautiful Siena, with free time to see the Cathedral of Siena
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 trip leader for the day
Maximum group size of 15
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See what people are saying

56 total reviews

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4.9/5 (based on 56 reviews)
5 stars
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3 stars
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1 stars
19 November 2022
M
Reviewed by
Michele simpson

Amazing experience!
13 November 2022
B
Reviewed by
Bridget Lynn

We absolutely loved this tour. The day flew by way too quickly. Our guide was amazing and knew so much about the region and towns. She gave us plenty of free time to roam around each of the towns. Strongly recommend it!

09 November 2022
B
Reviewed by
Brenda Nisbet

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Frequently Asked Questions

Where to meet?

Meet your guide at Viale Filippo Strozzi 1 in front of the small fortress. A friendly representative will be there holding a sign with our company name on it.

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. 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 (although your trip leader can give you some tips, of course!)

Are lunch and wine included in the price of this day trip?

Yes, it's all included in the tour price.

What if I don't like wine but I want to see Chianti and San Gimignano?

If you're not interested in a wine-focused day trip from Florence, feel free to contact us so we can make alternate plans for your travel to the countryside.

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.

Where to meet?

Meet your guide at Viale Filippo Strozzi 1 in front of the small fortress. A friendly representative will be there holding a sign with our company name on it.

Total: as low as $112.15

available days discounted days

24-hr cancellation on group tours! Learn more about our cancellation policy

Reserve Now $131.95 as low as $112.15
$131.95 as low as $112.15
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