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Tuscany Wine Tour from Florence to Siena & Chianti

Sample Local DOCG Chianti Wines and explore the picturesque towns of Siena and San Gimignano

5 / 5 See All 25 Reviews · 9.0h 18 max · Florence and Tuscany, Italy

Travel from Florence to a family-owned Tuscany farmhouse with stops in the medieval towns of Siena and San Gimignano. Explore the craft of winemaking with the vineyard's owners and taste the region's best wines.

Tour Details

Luxury Transportation from Florence
Rolling Hills of Chianti
Organic Farmhouse
Tuscan Cuisine for Lunch

Views of Chianti
San Gimignano
Transportation back to Florence
Historic Siena
Siena Cathedral

Do you want to visit the best wine region in the world? Do you want to be under the Tuscan sun like Diane Lane? Can you imagine a centuries-old horse race downtown that the people of Siena still obsess over? On this full day tour from Florence you will experience the marvel of Tuscany visiting the ancient city of Siena, the stunning hilltop village of San Gimignano and visit an incredible winery for a delicious lunch looking over the Tuscan hills. This 9 hour day trip hour tour includes:

- Round-trip transportation from the center of Florence in luxury, climate-controlled vehicle
-Expert tour of Siena including the Cathedral of Siena
- Wine tour and tasting at a traditional, family-run vineyard
- Generous lunch spread including some Tuscan favorites
- Visit to the small medieval hill town of San Gimignano

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Historic Siena

Your first stop on this Tuscany day trip is the famous city of Siena. Divided into 17 contrade (districts, each neighborhood is represented by a mascot and the rivalry is fierce. Each year, the city is home to the Palio. This horse race has been run since the middle ages and occurs twice a year in Siena's central square Piazza del Campo. On tour you will see the site of this great race as well as the city's great Cathedral. You will also learn about Siena's vast history in finance including being home to the oldest bank in existence.

San Gimignano - Medieval Manhattan

The next stop on this Tuscany Day Trip is an incredible place known as “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. In one of our favorite wine regions, learn about famous grapes and the wine-making process from vine to bottle! And of course, taste the local products for yourself, since what's better than wine and food? Sit down for a delicious lunch of locally-grown products from the family's farm, staying 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 a visit to a medieval village, it's time to head back to Florence. And because you're with us, there's no need to worry about catching trains or navigating the highways. Simply sit back and relax after your full day tour. All you have to do is enjoy the scenic ride back to Florence and your accommodations.

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What you get with this tour

English Speaking Guide

Transportation Included

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25 total reviews

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Average customer rating

5.00 / 5 based on 25 total reviews

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12/4/2019

Best idea ever.

My wife and I booked this tour in December for our Italy trip. Due to the time of year, we were the only ones scheduled that day for the tour. It honestly couldn’t have gone better. Three stops: Piazzale Michelangelo, the town of San Gimignano and the winery for some wine samples and lunch with views of Tuscany. Both of our guides were super informative and just a blast to hang out with. If you’re considering something like this to “get out” of Florence for a bit, this is it!!!’

Reviewed by
Stephen Barton

10/17/2019

A great day

This tour was relaxing, informative and such a great day from start to finish. After being in the cities for a little bit, getting outside to see Tuscany was a perfect option. The winery we went to was super welcoming and had a great spread of food and tastings for us. Thanks for a great day!

9/29/2019

Wine and Countryside

This day trip was easy, stress free, and a great way to get out to the countryside. We had a smaller group, about 8 of us, so we enjoyed talking about where we were from and where we had been traveling so far. The wineries provided a wonderful spread for lunch and the wines were enjoyable as well. From start to finish, a great day.

Frequently Asked Questions

Where to meet?

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?

* Sunscreen in the summertime. * A bottle of water * Comfortable walking shoes * An empty stomach!

I'd prefer a private day trip, can this be arranged?

Absolutely, yes! We offer a similar private day trip from Florence, including private transportation that will pick you up/drop you off directly from your Florence accommodation. Check our the tour description below, and enquire with one of our Travel Experts for more information. 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 fellow travelers.

Is a guide included on this day trip?

No, but you'll be accompanied by one of our fabulous staff members and a driver is included for the entire day so drink as much wine as you feel like.

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

Yes, absolutely. It's all included in the tour price.

What if I don't like wine?

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?

* Sunscreen in the summertime. * A bottle of water * Comfortable walking shoes * An empty stomach!

Where to meet?

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

See more frequently asked questions