Top 11 Winery Tours in Florence

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

From Florence, visit Siena with a local guide, admire its marble cathedral, eat and taste wine at Fattoria Poggio Alloro, wander San Gimignano, and finish at Pisa’s Square of Miracles. The $114.88 tour lasts 11 to 12 hours and offers a Leaning Tower upgrade.

“Unreal. Go on this. All I have to say. With my boys and having the best time. The tour hasn’t even finished and I wanna come back!”

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2.Chianti Wineries Tour with Wine Tasting

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

Ride from Florence to two contrasting Chianti wineries with an English-speaking guide such as Ana, Alex, or John. Tour vineyards and cellars, taste up to seven wines with cheese, salami, olive oil, and bread, then return by comfortable coach in about five hours.

“James Is our guide on the boat Thank you very much”

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

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

Spend a full day in Tuscany with guided Siena, free time in San Gimignano and Pisa, and an optional Chianti winery lunch with four wines. Guides such as Sara, Alessandro, and Giancarlo bring the history to life, while comfortable coach travel handles the long distances.

“Our trip was excellent and my friends and I really enjoyed our day. The guide was brilliant with so much knowledge of the areas we visited and really made our trip special. We loved seeing the Tuscan countryside and towns we visited.”

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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 10:00am for two Tuscan wineries, guided tastings of up to eight wines, olive oil and balsamic pairings, and time in San Gimignano. Guides such as Emanuele, Valentina, and Giovanni add local stories, while the air-conditioned minibus keeps the day simple.

“Ottavio guided a perfect day in Tuscany as we visited two wineries and the walled town of San Gimignano. On the drive from Florence, Ottavio kept us entertained with both personal stories of growing up in Tuscany and the history of the region. We could NOT have asked for a better experience or guide.”

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5.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

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

Travel from Florence to two Chianti wineries for tastings and a traditional Tuscan lunch, with time in medieval San Gimignano and a photo stop at Piazzale Michelangelo. Guides such as Lorenzo, Daniel, Christian, and Cecilia are praised for local stories, good humor, and relaxed pacing.

“This was part of an end of life trip for me (stage 4 cancer) with my two adult daughters and my oldest daughter’s husband. We are traveling to Venice, Florence, Rome, Catania, Sorrento, Naples. I love wine and wineries and so this was probably the excursion I was most looking forward to. Tour guide was great. First winery—very dynamic host and good wine. 2nd winery-not as personal, great lunch, but not great wine. Trip to San Gimignan beautiful and fun but felt rushed. Driver said he would take my daughter back after last winery to the place that specializes in tiramisu but he did not. Overall good-but we enjoyed the…”

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6.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 the Chianti hills. You’ll have about two hours to explore Siena independently, then visit two rustic wine estates for tastings, olive oil, and a Tuscan dinner. English and Spanish are guaranteed, with groups capped at 30, though some departures may be larger.

“Stop in Siena was lovely however arrived at winery too late in pitch dark unable to see surrounding views, castle etc. Dinner is not really a 4 course made out to be in the brochure with cheese & meats to start, a basic Lasagna followed by sliced pork and potatoes. No vegetables or salad ( even on a share basis would be ok) Dessert was really disappointing....Biscotti biscuit only. Not really value for money unfortunately.”

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7.Small Group Vespa Tour Tuscany Winery & Lunch

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

Ride a Vespa through quiet Chianti roads with FunInTuscany guides such as Lorenzo, Cecilia, Daniel, and Mido. After practice and photo stops, visit San Gimignano, taste Dondoli gelato, then enjoy a Tuscan lunch and local wines at a scenic winery.

“It was wonderful! Lorenzo and Marco were both wonderful hosts and the winery we visited had a stunning view with incredible lunch and wine!”

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8.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 with an English-speaking guide. Expect six wine tastings, a three-course lunch, cellar and vineyard time, and free time in both medieval towns. Guides such as Federica, Ana, and Francesco are known for keeping the day friendly and on schedule.

“Amazing trip .. you get a taste of the charming Tuscany .. it just makes you want to come back”

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9.Chianti Villages, San Gimignano and Winery Tour

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

Ride from Florence through Chianti’s vineyard country with an English-speaking driver such as Luigi, Francesco, or Simone. Visit wineries, taste local wine and olive oil, enjoy a light farm lunch, and spend free time among San Gimignano’s medieval towers.

“Great time. Informative host, nice winery’s. Overall a great time”

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10.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 people, visiting two Chianti wineries, tasting organic wines and local products, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Christian, Lorenzo, Max, and Guido are praised for keeping the day friendly and informative.

“Max was a fantastic guide and driver. Food, wine and company was great. Beautiful country.”

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

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

Ride from Florence’s Oltrarno district into Chianti Classico with a small group and local guide. Expect scenic country roads, olive groves, village stops, a family-run farm, homemade lunch, wine, and olive oil tasting. You need cycling experience, fitness, and a minimum height of 150 cm.

“We had a wonderful time, our guide was extremely knowledgeable and very helpful. The lunch and wine tasting were amazing. The bikes were easy to ride and our guide explained how to ride safely. This tour was a highlight of our trip and we would highly recommend it!”

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