6 Vineyard Tours in Florence Worth Booking

1.Half day Chianti Vineyard Escape from Florence with Wine Tastings

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53Our pick

Ride from Florence to two Chianti estates with an English-speaking guide, taste three to four wines at each, sample olive oil and local foods, visit cellars, and enjoy vineyard views. Guides such as Alex, Lorenza, and Cecilia have been praised for friendly, clear explanations.

“We had a fantastic half-day Chianti vineyard tour with our guide, Alex, and our driver, Constantino. Alex was super engaging — he personally checked in with each of us to see if we had any questions or needed recommendations for Florence, which was so thoughtful and appreciated. Constantino was a fantastic driver and made the ride smooth and comfortable. We visited two vineyards, enjoyed delicious wines, and even got to taste freshly made olive oil — a special treat in November! The Tuscan landscape was breathtaking with its fall colors, and it was the perfect morning trip out of Florence.”

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2.Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 775 reviews · 4 to 7 hours (approx.) · from $96Top rated

Set out from Via San Gallo with an e-bike, helmet, GPS route, and roadside support. Follow a self-guided route through Florence, Fiesole, olive groves, and forest to Poggiopiano vineyard, then return via Piazzale Michelangelo. John provides the setup and route briefing, but you ride independently.

“We loved our bike ride through Florence and into the Tuscan countryside. The hills were a bit challenging, but the e-bikes made it doable. Directions were great, and we even spotted our tour hosts out on bikes checking on us - which really made us feel safe. We stopped in a little town for gelato and then on to the winery, which was wonderful and relaxing. It really was a perfect day.”

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3.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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4.Chianti Vineyards Escape from Florence with Two Wine Tastings

★★★★★★★★★★4.5 · 280 reviews · 5 hours (approx.) · from $53

Leave Florence by coach for two Chianti estates along the scenic wine road. Tour cellars, vineyards, and olive groves, then taste several wines with cheese, salami, olive oil, and balsamic vinegar. Guides such as Emma, Anna, Alex, and Margherita have helped make this a friendly, easy half-day outing.

“One of our best experiences in Italy! We got to see the countryside and two locations of wineries. Both places were drastically different so it was neat to see different scales of doing things. I definitely learned a lot about wine!”

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5.Chianti Vineyards Tour with Wine Tasting & Dinner

★★★★★★★★★★4.1 · 226 reviews · 8 hours · from $128

Ride from Florence to a Chianti estate, tour the winery, and taste local wines before a candlelit dinner among the vines. Guides such as Aurora, Marta, and Luca have led guests through the wine and food. Expect a multilingual group, shared tables, and a late return.

“Such a great trip, more drinks and good than expected! I went solo but had a great time!”

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6.Wine Tasting and Dinner in Chianti Vineyards

★★★★★★★★★★4.6 · 192 reviews · 6.5 hours · from $141

Leave Florence with an English-speaking guide such as Chiara, Phillipa, or Gabriel, visit two very different Chianti estates, taste wine and olive oil, stop in Greve, then eat a multi-course Tuscan dinner paired with estate wines among the vines.

“Bus was comfortable, guide (Anna) was fun, tastings and food servings were generous, the wineries were beautiful and staff was very welcoming and educational. Definitely worth it!”

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