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
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 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 trip leader for the day
Maximum group size of 16
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 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.
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
See what people are saying
103 total reviews
Leave a reviewFun Day
Dara Fraser
Just the right balance of support and independence- happy with our choice! Meeting point easy and driver and guide ( I think Gianni & Sara) went above and beyond to give us an extra surprise at the end. Impressed tour went ahead in very nice van for just four visitors. Great value and very ethical policy.
Sarah williams
Was a good day out. Would prefer longer at San Gimignano than Siena. Lunch was amazing was lovely to sit and chat with everyone on our group. TBH I'm not sure why we had 2 tour guides and tbh I'm not sure why we had them at all, as they didn't give alot of information and we had free time in the 2 towns anyway. Overall was good, but not great compared to other tours we have just done.
Excellent way to see Siena & San Gimignano
Rosalind Odin
We had a really great time on this tour . There were 15 of us total and they divided us into two vans. Very comfortable and it was cool getting to know the other people on the tour. The tour guide, Manny, was s lovely Italian woman who spoke really good English. Unfortunately, she could only be in one of the vans at a time but she switched the one she ride in during the day. She was great at explaining history and the sites to see. I liked that they drove you to Siena and San Gimignan,, but let you explore on your own for a couple of hours. In the middle of the day, between towns , we went to a family owned winery that makes excellent Chianti and it was reasonable to buy their wine and ship bottles home, which is not typically . . They served us a very nice lunch there as well. All in all a really good day and I would really recommend this tour.
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 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?
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.
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