The 15 Best Chianti Wine Tours from Florence

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

/ August 13, 2026

1.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Our pick

One day tour from Florence to Pisa, San Gimignano, Chianti wine lunch, and Siena, with Leaning Tower tickets and optional guided walks.

“Barbara was an amazing guide! She made an already amazing tour even better. Sienna was very nice. Poggio Al Laghi, the winery was very nice! Great cuts and cheese plate & a great pasta dish! The host was cool & funny. San Gimignano... what can I say.... ot was absolutely stunning & the highlight of the tour for us. It was quite, gorgeous, had midevil vibes and AMAZING views. It's one of those places that you want to move to for a few months after visiting. Pisa was overall forgettable. I highly recommend this tour!!!”

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Florence: Chianti Wineries Tour with Wine Tasting

/ August 10, 2026

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Half-day Chianti wineries tour from Florence with two cantinas, guided tastings of 3-4 wines each, plus local cheese and olive oil.

“Great tour, fun guide and organized well, wineries visited were great!”

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

/ August 15, 2026

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

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

11-hour coach day trip from Florence to San Gimignano, Monteriggioni, Chianti and Siena, with lunch, wine tasting, and optional Duomo entry.

“Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

/ August 10, 2026

4.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

One-day Tuscany loop from Florence: Pisa, San Gimignano, Siena and Chianti views, with optional lunch and wine pairing.

“Hilary was fantastic.Kept everything on schedule and kept everything interesting fun and fresh”

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Chianti Wine Tour from Florence

/ August 16, 2026

5.Chianti Wine Tour from Florence

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

Chianti Wine Tour from Florence: two winery visits with tastings and local food, plus the scenic Via Chiantigiana drive in 5 hours.

“The 2 winery's we visited were very nice and the host at each was very engaged and helpful, wines, & food were good. The tour guide (Kayko) from the company was not very friendly and kept trying to rush us. telling us to use bathroom right away she would jump ahead of the presenter at the winery. Telling us to drink or spill so we could move on. If we had specific schedules, it should have been stated up front so eveyone knew what to expect”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour

/ August 16, 2026

6.San Gimignano, Siena, and Chianti Wine Tour

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

Small-group Tuscany day trip from Florence to Siena, Chianti winery with five tastings, and San Gimignano, plus truffle lunch.

“Marco was brilliant and we had a lovely day, with his guidance! We did sort of think that it would have been nicer to see San Gimignano earlier in the day, because after the travel and winery everyone is starting to flag and it was one of the key reasons we picked this tour.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence

/ August 19, 2026

7.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Florence to Siena, San Gimignano, Monteriggioni and Chianti in one day, with a guided Siena walk and a 3-wine tasting.

“Sara and Lorenza were great tour guides. Mario a safe bus driver. Bus was comfortable. Knowledgeable professional and most pleasant”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

/ August 20, 2026

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

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Florence to San Gimignano, Siena and Chianti for UNESCO sights plus a guided cathedral option, lunch, and a guided wine tasting.

“Absolutely loved San Gimignano… by far the favorite party of this trip. If I was to do it over I would skip the winery and stay here for more time. sienna was lovely as well. The wine tasting and lunch was average but the small towns were definitely the highlight. Aaron and Alexandra were great hosts and very knowledgeable!”

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From Florence: Chianti Half-Day Afternoon Tour

/ August 10, 2026

9.Chianti Half-Day Afternoon Tour

★★★★★★★★★★4.4 · 2,328 reviews · from $55

Half-day Chianti tour from Florence with two cellar visits, seven wine tastings, olive oil and balsamic samples, plus free time in Monteriggioni.

“We loved the tour, the wine places and the guide. Amazing experience. I would have loved it to last longer.”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

/ August 21, 2026

10.Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78Top rated

One full day from Florence to Pisa, Siena, San Gimignano, and Chianti vineyards, with a guided Siena walk, cathedral entry option, and lunch with 4 wines.

“It was a great trip, I’m a vegetarian and the food was great. We brought our daughter who was 14 months and the tour was great for her.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings

/ August 21, 2026

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

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

Half-day Chianti escape from Florence with two winery visits, cellar tours, tastings of 3 to 4 wines per estate, plus views.

“Loved this experience. I’m not much of a wine drinker but I had to go to a vineyard in Italy and I’m glad I did. I also loved that this was two different vineyards. The one downfall is that we only had reds and I prefer whites so I would have liked more variety.”

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Chianti Vespa Tour with Lunch from Florence & E-car Option

/ August 10, 2026

12.Chianti Vespa Tour with Lunch from Florence & E-car Option

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125

Ride a classic Vespa or electric Topolino through Chianti with winery tastings and lunch from Florence, in a small group with rain options.

“Amazing experience. Loved every minute! Clear instructions and thorough check of our ability to drive a Vespa before we departed. We spent more time driving our vespas throughout the Tuscan countryside, than I thought we would. So many “pinch me” moments! And then to top it all off, an amazing 3 course meal and wine tasting experience at a local winery. 10/10!”

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Bike Tours in Florence, Chianti Wine Tours, Cycling Tours, Florence Tours, Food & Drink, Tour Reviews, Tours, Tuscany Day Trips, Wine Tastings in Florence, Wine Tours

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

/ August 28, 2026

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

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

From Florence, bike through Chianti hills and olive groves, then taste wines and olive oil at a medieval castle with lunch.

“This tour was an amazing experience in the Tuscan country side. Angus did a great job leading us through the country side on bikes. He stopped at several points for photo opportunities and share info about the area. The wine tasting and lunch at the castle was a perfect end to the morning. The biking is 12 miles long and you do need to be able to navigate some hills.”

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