Chianti Tours and Trips 2024/2025

We offer 6 tours in Chianti having in total 42 customer reviews. Tour durations range from 4 to 8 days and the top tour categories in Chianti are food tours, wine tasting tours & trekking and hiking. Out of the 6 trips in Chianti, 3 of them are private tours and 4 are group tours. Our Chianti tours are offered by 6 qualified and hand-picked tour operators and each Chianti trip comes with a best price guarantee and no added booking fees.

6 Trips in Chianti with 42 Reviews

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Tuscany Walks & Chianti Wines

of 38 reviews
  • Best price guaranteed
  • No booking fees
One week of great walks , great hospitality and great food .. superb leader in Mark and combined wit ...
  • Tour Type Small Group Tour
  • Activities Trekking and Hiking & Food tours
  • Accommodation Hotel
  • Transport Train
  • Age Range 18-95 yrs
  • Operated in English
days08 From US$ 2,617 US$ 2,245
SavingUS$ 372
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  • Brochure Price:US$ 2,617
  • Special Deal (14%):- US$ 372
  • Total Price from:US$ 2,245
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Next Departures
  • Oct 12 Only 8 seats left
  • Oct 19 Only 8 seats left
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Small Group Chianti & San Gimignano Sunset Wine Tour

  • Free cancellation
  • Trip customizable
On this day trip you will visit Chianti, Tuscany and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Beer and drinks tasting
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours08 From US$ 192 View Tour
Next Departures
  • Oct 02
  • Oct 05
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Private Gourmet Wine Tour in Tuscany

of 2 reviews
  • Free cancellation
  • Trip customizable
What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations ...
  • Tour Type Private Tour
  • Activities Food tours & Wine tasting tours +1 more
  • Accommodation Hotel
  • Transport Train
  • Age Range 22-89 yrs
  • Operated in English, German
days04 From US$ 2,368 View Tour
Next Departures
  • Oct 01
  • Oct 02
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Small Group Chianti and Castles Wine Tour from Siena

  • Free cancellation
  • Trip customizable
8 hour farm and plantation visits trip through Chianti and Siena. Read More
  • Tour Type Small Group Tour
  • Activities Farm and plantation visits & Wine tasting tours
  • Accommodation No Accommodation
  • Age Range 5-79 yrs
  • Operated in English
hours08 From US$ 192 View Tour
Next Departures
  • Oct 03
  • Oct 07
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The Tuscan Dream

of 1 review
  • Trip customizable
  • Best price guaranteed
Excellent customer service! Deal was fantastic!
  • Tour Type Independent Tour
  • Activities City sightseeing
  • Accommodation Hotel
  • Transport Private Vehicle, Boat, Bus, Coach & Train
  • Age Range 8-95 yrs
  • Operated in English
days07 From US$ 787 View Tour
Next Departures
  • Oct 03 10+ seats left
  • Oct 10 10+ seats left
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Rome, Florence & Tuscany Family Adventure

  • Trip customizable
  • Best price guaranteed
8 day food tour through Rome, The Vatican, Florence and 4 other destinations in Italy. Read More
  • Tour Type Private Tour
  • Activities Food tours & Museum and gallery visits +4 more
  • Accommodation Hotel
  • Age Range 6-99 yrs
  • Operated in English
days08 From US$ 7,002 View Tour
Next Departures
  • Oct 01
  • Oct 02
Showing 1 - 6 of 6 results
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Chianti Tour Reviews

5 - Excellent
Based on 42 customer reviews
Right First Time!
5 - Excellent
  • Anonymous
“This was our first actual trip with this tour company and it was all that we hoped for, and more. The balance of walking, wine tasting and culture was spot on! Villa Casalta accommodation was great - simple in a traditional way, owner and Marguerite warmly welcoming and helpful, beautiful swimming pool (used by several of us even though it was end of Sept), entertaining dog (Stella) and cat, with only a slow off-road 20 minute walk to pretty town of Castellina.”
Tuscany Walking and Wine
5 - Excellent
  • Anonymous
“A really enjoyable and varied week in Tuscany. Three lovely walks through forests and vineyards. Stunning hilltop villages and market towns. Excellent wine tastings and winery visits, each a little different, and we certainly drank a lot of local Chianti. Liz, our guide, was efficient, knowledgeable, capable and so friendly. We had plenty of time to explore the cities of Siena and Florence at our own pace, and on our free day most of us opted for a cookery class at a local restaurant. Enormous fun and the lunch we helped produce, was amazing. The family run farmhouse where we stayed was full of character, and they made us so welcome. The evening meals were generous and based on local produce and served with their own estate wines.”
A perfect mix of walking, wine tasting and sight-seeing
4 - Very Good
  • Anonymous
“This was my 10th trip with this tour operator in 4 years so I am already a fan and it almost provided us with what we'd hoped for. There was a good balance of walking, wine tasting and sight-seeing. The days spent in Florence, Siena and San Gimignano were not at all rushed and we had ample time to do all that we planned. It was also great to be driven in by Simon our wonderful guide. It meant that we spent very little time travelling. Villa Casalta accommodation was simple in a traditional way and our room was beautiful and very clean. We were given a very warm greeting from Roberta on our arrival and she waved us off on our departure however for the rest of the week we hardly saw her. The swimming pool was lovely to sit around but very cold to swim in during October although I did mange it one afternoon. The location is lovely with a pleasant 20 minute walk to pretty town of Castellina along a gravel road.”
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