12 Winery Tours in Florence the Drive Pays For

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Spend 11 to 12 hours touring Tuscany by air-conditioned coach, with guided Siena and cathedral visits, free time in San Gimignano and Pisa, and a family-run winery lunch with four wine tastings. Guides such as Alex, Sara, Davide, and Manolo are known for clear directions, humor, and good pacing. Choose the Pisa tower upgrade if you want to climb.

“I had a fantastic experience with this tour guide Sara and Milano from start to finish. Everything was well-organized, smooth, and thoughtfully planned, which made the entire tour stress-free and enjoyable. Sara was knowledgeable, engaging, and passionate, sharing interesting facts and stories that really brought the place to life. Sara also very friendly, patient, and happy to answer all my questions. The pacing was perfect, and I never felt rushed, while still getting to see and learn so much. Overall, it was a truly memorable experience, and I am so glad I chose this operator. Highly recommended for anyone looking for a professional, informative, and enjoyable tour!”

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2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Best value

Travel from Florence to two Chianti wineries in about five hours. Meet local producers, walk through vineyards, taste up to seven wines, and sample cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Ana, Alex, John, and Martina add regional stories along the way. Morning departures offer the best light for vineyard views.

“The tour was amazing, we had a great time with Ana, she is great and kind. We visited two wineries, but the first one, La Lama, was amazing. You will not regret this experience.”

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3.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Spend 12 hours exploring Tuscany by comfortable coach, with a guided Siena walk, free time in San Gimignano and Pisa, and an optional farmhouse lunch at a Chianti winery. Guides such as Sara, Alessandro, and Giancarlo are known for lively storytelling. Choose the lunch option for wine tasting and countryside views, or skip it for more time in San Gimignano.

“Excellent trip, our guide Genevra was fabulous and our driver Giuseppe was fantastic. Would definitely recommend this trip.”

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4.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229

Leave Florence at 10am with guides such as Emanuele, Valentina, or Giovanni for two winery visits, eight wine tastings, local food pairings, and 90 minutes in San Gimignano. You’ll travel by air-conditioned minibus through Chianti country and return around 5pm. Lunch is not included, and the tour is for adults 18 and older.

“All positive- the people we never met before but had the opportunity to socialize with during this tour, the wine, the small town we explored, and the tour guides! Absolutely worth it.”

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5.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Spend about eight hours with a small group of up to 16, visiting two Chianti wineries, tasting local wines, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Lorenzo, Christian, Cecilia, and Leonardo are praised for lively stories and good pacing. Round-trip transport from central Florence is included.

“It was a lot of fun and Cecilia was a wonderful guide with a great personality. She made it fun and the whole group were friends by the end of the trip.”

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6.Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

★★★★★★★★★★4.8 · 594 reviews · 7 hours · from $201

Leave Florence at 10:00am for two Chianti-area wineries, tasting up to seven wines with olive oil, balsamic vinegar, and local food. Guides such as Dom, Anna, Valentina, and Alessandro add local stories along the way. You’ll also get 1.5 hours to wander San Gimignano before returning to Florence around 5:00pm.

“Lorenzo was amazing! This was the perfect trip. When picking a day trip in to Tuscany, we wanted one that gave us ample time at each stop, (especially San Gimignano.) we were so excited to get to visit Torciano with their impressive tasting!”

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7.Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

★★★★★★★★★★4.0 · 324 reviews · 7 hours 30 minutes (approx.) · from $106

Leave Florence at 2:45 pm for Siena and Chianti. You will have free time in Piazza del Campo, visit two rustic wine estates, taste Tuscan wines and olive oil, and eat a four-course dinner. English and Spanish are guaranteed, with groups advertised at up to 30 people.

“We had the opportunity to explore the beautiful medieval city of Sienna and later a wine testing accompanied with dinner.”

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8.Small Group Vespa Tour Tuscany Winery & Lunch

★★★★★★★★★★4.9 · 268 reviews · 7 hours · from $235

Leave Florence in a small group of up to eight, learn to ride a Vespa on quiet Tuscan roads, and travel through Chianti to San Gimignano. Guides such as Lorenzo, Cecilia, Daniel, and Mido help nervous riders feel safe. Finish with a Tuscan lunch and wine tasting at a local winery with broad countryside views.

“This trip was so much fun!! Everything was planned out so well and the tour guides were fantastic. I rode with Lorenzo (the best tour guide) because I was not comfortable driving myself, and it honestly was even better because I didn’t have to worry about a thing and could just take in the scenery! Stopping at the town halfway was great too, because I wouldn’t have had an opportunity to see it while in Italy (plus the famous gelato shop was so good!). The vineyard was also beautiful with lots and lots of wine! And the meal was also great. Our group got along really well, which made for…”

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9.Tuscany, Siena, San Gimignano & Winery Lunch

★★★★★★★★★★4.7 · 184 reviews · 5 - 9 hours · from $93

Travel from Florence to Siena, a family-run Chianti winery, and San Gimignano in a comfortable air-conditioned vehicle. You’ll get guided introductions, free time in both medieval towns, a cellar and vineyard visit, six wines, and a three-course Tuscan lunch. Guides such as Ana, Federica, Francesco, and Lori are known for keeping the day friendly and well organized.

“Towns we visited a were fabulous. Only wished we had a bit more time . Lunch was great with vineyard visit”

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10.Chianti Villages, San Gimignano and Winery Tour

★★★★★★★★★★4.7 · 95 reviews · 6.5 - 7 hours · from $199

Travel from Florence through Chianti’s vineyards and olive groves with an English-speaking driver such as Luigi, Francesco, or Simone. Tour a cellar, taste local wines and olive oil, explore San Gimignano, then enjoy a light lunch with wine at a farm or wine estate. Expect a relaxed 6.5 to 7-hour outing in a small van.

“Aladdin was fantastic. He knew to take us to Piazzale Michaelangelo on our way out because the weather was perfect for pictures! Was the perfect day trip from Florence. So fun to see the Chianti vineyards and taste the wines. Aladdin was so helpful and informative! Highly recommend!”

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11.Wineries, Tastings, Lunch & San Gimignano Day Trip

★★★★★★★★★★5.0 · 82 reviews · 8 hours · from $223

Spend eight hours with a small group of up to eight, visiting two Chianti wineries, tasting wine and olive oil, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Christian, Lorenzo, and Guido are praised for making the day lively and easy to follow. Expect beautiful countryside, a famous gelato stop, and a full schedule.

“Lunch was not great considering the price paid for the trip. Would be better if able to visit a winery to see how wine is actually made rather than just 2 wine tasting sessions.”

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12.Chianti E-Bike Tour with Tuscan Lunch & Winery

★★★★★★★★★★5.0 · 42 reviews · 7 hours · from $175

Ride from Florence’s Oltrarno into Chianti Classico with a small group of up to 10. Guides such as Ale, Claudio, Giovanni, and Andrea lead you along country roads to a family-run farm for homemade lunch, wine, and olive oil tasting. Expect hills, scenic stops, and some city traffic.

“The tour was fantastic from start to finish. My wife and I chose the full-day option and were treated to some truly stunning views. Lunch at the farm was delicious and full of flavor. Our guide, Andrea, was outstanding—since we were the only ones on the tour, he was able to take us to a few extra spots. The e-bikes made the ride both easy and enjoyable. Highly recommended!”

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13.Chianti Wine Tour with 3 Wineries & Tuscan Lunch

★★★★★★★★★★4.7 · 36 reviews · 7 hours · from $234

Spend seven hours in Chianti with a bilingual guide such as Toto, Luca, or Giovanni, visiting three family-run wineries, historic cellars, and an organic farm. Taste Chianti and other local wines, sample extra-virgin olive oil, and enjoy a multi-course Tuscan lunch. The group is limited to eight, with transport from Florence.

“Our guide, Giovanni, was knowledgeable, friendly, and made the whole day fun and engaging. The wines, olive oils, and lunch were absolutely top-notch. Communication from the company was clear and timely from start to finish. We had such a great time that we’ll definitely be booking again on our next trip to Italy! Each winery we visited was warm and welcoming, and the wines were absolutely excellent. I would highly recommend this tour to anyone looking to enjoy great wine, learn something new, and have a truly memorable day!”

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