Chianti Wine Tours

TUSCANY

10 Best Chianti Wine Tours In Tuscany

Tuscany's standouts.

The 10 chianti wine tours travellers book most often across Tuscany. Each one with the price you pay, the operator behind it and the day you actually get when you turn up.

10 Best Chianti Wine Tours In Tuscany

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

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting Point and the Pace You Should Expect (12 Hours)

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

Most Popular★ 4.5

One long day stitching together Pisa, San Gimignano, Chianti wine, and Siena, with optional Tower tickets and a guided Siena walk.

“We booked this tour based primarily on visiting Pisa. At the end of the tour it was our least favorite stop. However, we were pleasantly surprised with the other locations on this tour. This tour is great way to see a few stops in the Tuscany region in a short amount of time. Wine tasting…”

8,393 reviews12 hoursFrom $52by Sightseeing Experience

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Florence: Chianti Wineries Tour with Wine Tasting

Florence: Chianti Wineries Tour with Wine Tasting - Piazzale Montelungo Meeting Point: Easy to Find, Close to the Action

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

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Getting to the bus: Piazzale Montelungo basics (don’t wing it)

Chianti Wine Tour from Florence

Chianti Wine Tour from Florence - First Winery Stop in Chianti Classico: Organic, Cozy, and Food-Forward

4.Chianti Wine Tour from Florence

★ 4.5

Two organic Chianti wineries, expert-led tastings, and Via Chiantigiana views from Florence. Food included and you can buy bottles home.

“The half day tour was fun but was a bit chaotic going back and forth between Italian, English and Spanish. The group was divided into groups once we reach the wineries but was so loud at the first stop I couldn’t understand a word our guide was saying. The second stop, each group was a…”

3,979 reviews5 hours (approx.)From $59.13by CAF Tour and Travel

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

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Fortezza Medicea stop: the small walk that sets the tone

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

★ 4.5

Tuscany day trip from Florence with Siena, Chianti wine tastings and lunch, plus San Gimignano towers. Small-group transport and 5 wines.

“Marco was a fantastic guide with relevant and interesting information, while also leaving a good amount of free time to explore by yourself. When we boarded the bus we were offered an optional lunch at the Winery for an additional fee (€20) which most people took up and it did make for a more enhance…”

3,762 reviewsFrom $164.26by My Tour in Italy

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

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Getting From Florence: Piazzale Montelungo and the Bus Rhythm

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

★ 4.6

Florence day trip to San Gimignano and Siena UNESCO sites plus a Chianti winery lunch with three wine tastings and optional cathedral entry.

“Fantastic Day Trip! We had a wonderful experience on this tour. Guides, Marta and Stella, were incredibly friendly, knowledgeable, and organised. They made sure everyone was comfortable and informed throughout the day. Our driver, Elis, was professional and smooth—navigating the scenic Tuscan roads with ease. This tour is a great value for the price and…”

2,427 reviewsFrom $89.50by CAF Tour & Travel

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From Florence: Chianti Half-Day Afternoon Tour

From Florence: Chianti Half-Day Afternoon Tour - 6 hours in Chianti: how the pacing and timing feels in real life

7.From Florence: Chianti Half-Day Afternoon Tour

★ 4.4

Half-day Chianti from Florence with 2 wineries, 7 wine tastings, Tuscan olive oil and balsamic bites, and a medieval stop in Monteriggioni.

“Guide was excellent, giving us information in 3 different languages back to back throughout the bus ride. Both vineyards were great but really different, meaning you get to experience a real contrast in how wine is made.”

2,328 reviewsFrom $55.80by My Tour in Italy

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

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Price and value: what you’re paying for (and what you aren’t)

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

★ 5.0

Florence day trip to Pisa, Siena, San Gimignano and Chianti, with guided walks and a four-wine lunch tasting.

“The Duomo Di Siena is the most beautiful cathedral in the world! I am SO grateful to have been able to visit it. Just wish I had more time to visit it. Wonderful trip! Great guide!”

2,283 reviews12 hours (approx.)From $78.60by CAF Tour and Travel

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Half day Chianti Vineyard Escape from Florence with Wine Tastings

Half day Chianti Vineyard Escape from Florence with Wine Tastings - The big coach reality: group size, walking, and comfort

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

★ 4.5

Half-day Chianti escape from Florence with visits to two wineries, scenic Chianti Road drives, and tastings of Chianti plus local bites.

“It was a nice trip! The tour guide lady explained everything well, think her her is Laurence. The two farms were nice. The first tasting we were too many for the room, suggest to give it a more personal touch. The views were spectacular. We went end October and Autumn was in full bloom. It…”

2,196 reviews5 hours (approx.)From $53.10by Ciao Florence Tours Srl

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Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

Essence of Chianti Small Group Tour with Lunch and Tastings from Florence - Stop 2: Greve in Chianti—Piazza Matteotti and Falorni

10.Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

★ 5.0

A small-group Chianti day from Florence: 3 winery tastings, Greve stroll, and an included Tuscan lunch with wine and olive oil.

“This tour was a 10/10. The three wineries were all fabulous and beautiful. And our guide Alessio was top notch. He went above and beyond and was incredibly knowledgeable about Florence. Was a wonderful day all around.”

1,269 reviews8 hours (approx.)From $180.19by Prestige Rent

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