Chianti Wine Tours: 15 to Book out of Florence

1.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Our pick

Travel by comfortable coach from Florence to two Chianti wineries for guided tastings, vineyard walks, and samples of cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Anna, Alex, Martina, and John have been praised for bringing Tuscany’s wine, villages, and farming traditions to life. Expect about 5 to 5.5 hours, with no hotel pickup or lunch.

“The tour was great. We had first a visit to a traditional small vineyard from a Italian family, great wine and food, and the Nona was super nice with us. We saw the grapes plantations, drank wine and they were good and had snacks. Second one was way bigger, so more comercial, but it was super cool to see the difference between them, specially cause the second one was more than 100years old. The guide knew a lot about the region, and she even gave us recommendations about Florence. Everything went well”

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2.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Spend 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, a Chianti winery lunch and tasting, and guided Siena options. Guides such as Sandro, Marta, Ricardo, and Ilaria have earned praise for clear, friendly leadership. Choose the cathedral upgrade if Siena art matters to you.

“Beautiful towns, gorgeous food and lovely hosts! The tour started on time and it was well organised. The bus was very comfortable with free wifi and plugs for you to charge your phones. Our hosts were very accommodating and attentive to our needs. Many thanks to AARON and LILY for being our guide and to PLACIDO for driving us to our destinations safely.”

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3.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Leave Florence by air-conditioned coach and follow the Via Chiantigiana through vineyards, olive groves, and hill towns. Visit two organic wineries, taste six or seven Tuscan wines with local foods, and tour vineyards and cellars with wine makers. English and Spanish tours are available, with optional cooking and lunch upgrades.

“The first winery was just okay but the second was really nice because of the property. The hosts were fun.”

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4.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Leave Florence for Siena, a Chianti estate, and San Gimignano on a nine-hour guided tour. Expect air-conditioned transport, free time in both medieval towns, five wine tastings, olive oils, balsamic vinegar, and Tuscan dishes such as truffle lasagna and ribollita. Guides including Marco, Lyla, Marta, and Enrieta have earned particular praise for their energy and organization.

“Great trip, Martha was an excellent guide and made the entire trip fun. Definitely recommend this”

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5.S. Gimignano, Siena, Chianti Wine Tasting & Lunch

★★★★★★★★★★4.6 · 3,102 reviews · 11 hours · from $82

From Florence, ride through the Tuscan countryside to San Gimignano, a Chianti winery, Siena, and seasonal Monteriggioni. You get free time, local guides, three wines, Vin Santo, and a three-course lunch. Guides such as Marta, Ricardo, Sandro, and Alessandra are praised for clear directions and good humor, though Siena time can feel short.

“The trip was great! A very easy day out without feeling rushed or feeling like travel time was long. Coach was comfortable and ride was smooth. Guide Hilary was professional, yet enthusiastic. Lunch and wine at vineyard was excellent. before the trip i was a little fearful due to long duration. but i thoroughly enjoyed myself and wished did not end :)”

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6.Chianti Half-Day Wine Tour with Tasting

★★★★★★★★★★4.5 · 3,031 reviews · 6 hours · from $58

Leave Florence by tram and air-conditioned coach for two Chianti wineries, seven wine tastings, olive oil, balsamic vinegar, salami, cheese, and bruschetta. You will also stop at Monteriggioni. Guides such as Luca, Marco, Tula, and Alicia have led recent departures, while the 75-minute winery visits can feel brisk.

“Excellent service, right on time. Lyla and Claudio were fun and entertaining. The bus was clean. The wineries a little rushed, not much time to enjoy the vineyards. But the wineries personal excellent as well. I highly recommend.”

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

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

Ride from Florence to two Chianti estates with an English-speaking guide, taste up to six to eight wines with olive oil, cheese, and balsamic vinegar, and tour vineyards and cellars. Guides such as Alex, Lorenza, and Cecilia have earned praise for clear, friendly explanations, though the group may reach 43 people.

“The wine tour was very fun and informative! A nice bus ride through Tuscany and an experience of two different wineries. Both places were very accommodating and the wine & additional tasty treats were very good. We had a nice sunny cool day in December and the scenery was beautiful!”

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8.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145Top rated

Leave Florence by van for a roughly 12-mile ride through Chianti’s vineyards, olive groves, villas, and country roads. Guides including Ben, Filippo, Angus, and Alessio lead the route, with photo stops, a castle wine tour, olive oil tasting, and Tuscan lunch. Regular bikes are included. E-bikes cost extra and require advance notice.

“After check in at the meeting point, we started with a short van ride to the castle where we were outfitted with well maintained bikes, helmets and water bottles. Ben was a great guide and Lorenzo was great support. We had a good mix of skill levels and all did well. The winery tour at the castle along with the food and wine were very nice at the end. pro tips: - take the bio break before you leave the meeting place as the next one available is after the ride - if you're not a regular cyclist and want to complete the entire ride, consider the e-bike option to…”

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9.Chianti Tour with Two Wine and Food Tastings

★★★★★★★★★★4.5 · 1,205 reviews · 5 hours · from $58

Travel from Florence along the Via Chiantigiana to two family-run organic wineries in Chianti Classico. Expect cellar visits, vineyard walks, guided tastings, olive oil and Tuscan snacks, and a friendly English or Spanish-speaking guide. The optional morning cooking class adds lunch and four premium wines.

“We really enjoyed the tour. Once on the bus it was a very easy and relaxing trip. Our bus tour guide Keko was very informative. She pointed out a place with the Verrazzano family name on it that's connected to the Verrazzano bridge from my hometown NYC. The two wineries were great altho the second one was my favorite. Our tour guides for the winery I believe one of their names was Fernando (probably wrong but he had black hair) he did our tasting and the other guy's name sheesh can't remember started with an "A" (he had red hair) he started the tour either way they both were fantastic…”

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10.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours

Spend six hours in Chianti with a guide such as Anna, Chiara, or Andrea, visiting Radda in Chianti and two wine-tasting stops. Expect six local wines, cold cuts, cheese, bread, and olive oil, plus a winery visit and free time for village shopping. Confirm your Florence pickup point, since hotel pickup may be possible.

“we loved the 2nd wine tour. The host was very engaging and made us laugh a lot while we sampled the wines.”

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11.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

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

Spend about eight hours with a guide such as Lorenzo, Daniel, Christian, or Cecilia, visiting two Chianti wineries, tasting several local wines, eating a Tuscan lunch, and wandering San Gimignano. Round-trip transport from central Florence keeps the day simple, while a stop at Piazzale Michelangelo adds a fine city view.

“Enriching experience with a professional and fun staff who paid attention to everyone’s needs. The entire tour was extremely well handled and my wife and I could not been any more pleased. Breath taking views and with detailed guide information by Leonardo is a must. The wine tasting staff were very accommodating and taught the small group how to taste and observe the quality of the wines. Learning, laughter, and scenery was an amazing experience. Thank you so much to the “Fun in Tuscany,” especially Leonardo who really went the extra mile to ensure all we’re having a great time.”

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12.Tuscany Day Trip: Chianti & Cooking Class Small Group

★★★★★★★★★★4.5 · 770 reviews · 11 hours 30 minutes (approx.) · from $167

Spend about 11.5 hours in Tuscany with a guide such as Marco or Marta, traveling by air-conditioned coach or minivan. Visit four hill towns, join a hands-on cooking class at Poggio Ai Laghi, eat what you prepare, and taste wine at two estates. Expect free time, steep streets, winding roads, and a long but rewarding day.

“This was a small group tour. I would recommend to purchase tickets for Siena sites ahead of time so that you save time and not stand in cues. The wine tasting and lunch at Poggio ai Laghi in Monterioggioni was so much fun and the views at San Gimignano were spectacular.”

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13.Chianti Wine Tour with Tasting

★★★★★★★★★★4.5 · 729 reviews · 5.5 hours · from $41

Leave Florence by air-conditioned GT coach for two winery visits in the Chianti hills. You will taste three to four wines at each estate, sample olive oil, cheese, meats, and other Tuscan foods, and learn from a live English-speaking guide. Guides such as Martina, Chiara, and Frederica have earned praise for their friendly, practical approach.

“Tour was amazing and tour guide was very knowledgeable ! He provided tips during the ride. Overall this was a wonderful add on for our first time in Italy . Thank you”

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14.Chianti and Castles Tour with Wine Tastings

★★★★★★★★★★4.6 · 631 reviews · 5 hours · from $100

Spend five hours touring Chianti from Siena in a climate-controlled minivan with up to eight people. Visit Castellina in Chianti, Monteriggioni, scenic viewpoints, and two wineries, often including Poggio ai Laghi and Lornano. Guides such as Fabio, Daniel, and Tsvetelin are praised for clear local insight, while tastings pair Chianti wines with snacks, olive oil, and balsamic.

“Thanks to our friendly and informative guide Tsvetelin we had a lovely relaxed day. Would recommend this tour to visit both the villages and for the wine tasting.”

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15.Total Immersion Wine Tour in Chianti

★★★★★★★★★★4.9 · 430 reviews · 2 hours · from $47

At Fattoria di Montemaggio, guide Francesco or Ilaria leads you from a 600-meter rooftop view to the vineyard, cellar, and tasting room. Learn about organic farming, Chianti Classico, wine service, and grappa, then sample five estate products with cheese, salami, bread, and olive oil. Bring a car and follow the road directions closely.

“Franceso was great very passionate about the boutique vineyard & explained lots about the history & the area. Wines were delicious & purchases were made to enjoy during the rest of our holiday. Would highly recommend going!”

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