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 5 / 5 See All 28 Reviews · 9.00h 15 max · Florence, Italy

Looking for the easiest way to explore Tuscany from Florence and take in the best wineries in Chianti and views in San Gimignano? Then you've found the perfect tour! Sit back and let your passionate tour leader and driver take care of the driving as you wander from Florence to the Tuscan countryside and taste delicious food and wine from local, organic farms and vineyards. Explore other medieval towns before getting to know the locals and their traditional winemaking processes.

Tour Details
  • A memorable experience
  • Luxury transportation from Florence
  • Rolling hills of Chianti
  • Historic Siena
  • Siena Cathedral
  • San Gimignano
  • Views of Chianti
  • Organic farmhouse
  • Tuscan cuisine for lunch
  • Transportation back to Florence

Meet your trip leader in Florence at Viale Filippo Strozzi 1. Hop aboard your luxury, climate-controlled vehicle with no more than 15 other people and enjoy an entertaining ride through the most famous wine region in Italy. Tuscany awaits to share its bounty of local foods and wines from friendly locals who love sharing their passion for winemaking. You'll also get to explore the ancient towns of San Gimignano and Siena before enjoying lunch in Chianti. Your 9-hour day trip from Florence includes:

  • An English-speaking trip leader for the day

  • Round-trip transportation from Florence in luxury, climate-controlled vehicle

  • Visit to Siena including the Cathedral of Siena

  • Visit to the small medieval town of San Gimignano

  • Wine tour and tasting at a traditional, family-run vineyard in Chianti

  • Traditional Tuscan lunch included

Historic Siena

Your first stop on this Tuscany day trip is the famous city of Siena. Each year, the city holds the famous Palio horse race that has been run since the Middle Ages twice a year in Siena's central square Piazza del Campo. You'll see this famous square and the Cathedral of Siena, plus the oldest bank in existence.

Medieval San Gimignano

The next stop on this Tuscany day trip is an incredible place often nicknamed “Medieval Manhattan.” A UNESCO World Heritage site, San Gimignano is known for the towers that bring to mind modern day skyscrapers. Once inside the city walls, enjoy some free time to explore this remarkable and historic town. 

Chianti Farmhouse for Wine and Lunch

Continue your journey through the Chianti hills and olive groves before arriving at a traditional family-run farmhouse. Learn about famous grapes and the winemaking process from vine to bottle before sampling them yourself. Sit down for a delicious lunch of locally-grown products from the family's farm that stays true to the Italian slow food movement and traditions of Tuscan cuisine. Lunch and wine are included.

Chianti Region to Florence

After a full day of Chianti wine tasting and visiting historic Tuscany cities, it's time to head back to Florence. Simply sit back and relax after your full-day tour of wining and dining and let your professional driver take you safely back to Florence.

What you get with this tour
Transportation Included
English Speaking Guide
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28 total reviews

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5.0/5 (based on 28 reviews)
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One of our trip highlights!!
06 July 2022
H
Reviewed by
hannah pelletier

We loved everything about this tour! Our tour guide was lovely and informative. Our driver pointed out highlights along the way! Each stop on this tour was equally amazing. Siena was beautiful. you have plenty of time to explore the cathedral and do some shopping as well. The wine tasting was delicious and you can buy plenty of wine to take home. We loved getting to know other people on the tour during this time. San Gimignano was breathtaking! I am so glad we did this and recommend it to anyone staying in Florence.

A MUST DO when in Florence!
18 October 2021
D
Reviewed by
Donna L Harper

So happy we chose this tour. Our tour guide was outstanding. Giving just the right information needed without giving TOO Much. The wine tasting experience was the best one I've had. They made it so easy to order and ship wine back to our home. There are two other none wine tasting stops included. I am so glad we did them too.

09 August 2021
C
Reviewed by
Christopher Sherwood

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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 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 cities 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 tour leader and a driver the entire day.

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 cities and vineyards.

Where to meet?

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

Total: $125.95

available days discounted days

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

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$125.95 / per person
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