Where to Ride: the 4 Best Horse Riding and Wine Tasting in Italy

1.Horseback Riding with Wine Tour from Florence

★★★★★★★★★★5.0 · 60 reviews · 8 hours (approx.) · from $229Our pick

Spend about eight hours in Tuscany with guides such as Stefano, Daniel, Giacomo, or Christian. Ride gentle horses through the countryside, explore San Gimignano and its 1300 Museum, then enjoy a generous Tuscan lunch and local wine at a family-run winery. Small groups, transport between stops, and no riding experience required.

“My sister and I loved this tour! Our guide Michele was so fun and knowledgeable. The food and wine at the vineyard was fantastic. This is the perfect was to spend a day in Tuscany from Florence. Highly recommend!!!”

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2.Horseback riding & Wine Tasting and snack Lunch at noble Estate

★★★★★★★★★★5.0 · 53 reviews · 5 hours 30 minutes (approx.) · from $356

This private Florence outing pairs a one-hour guided horseback ride with a two-hour visit to a historic Chianti estate. Simona and Marco handle the transfers, while riding guides such as Stefano tailor the pace to your ability. At the winery, you tour medieval cellars and Renaissance rooms before tasting Chianti wines with a Tuscan lunch.

“This trip was so much fun! A lovely break from the city to ride horses and see the best views of the countryside. Simone was the best host & was able to help all of us since we had different skills riding horses. The winery tour with Constance was amazing - she really loves her work & it comes through in everything she talks about - she gave my kids a great wine education, which they loved! Highly recommend this tour!”

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3.From Florence: Horse Ride and Wine Tour at Estate with Lunch

★★★★★★★★★★4.9 · 42 reviews · 5 hours · from $377

Leave Florence with Simona or another English-speaking guide for a 1.5-hour ride through southern Chianti. Calm horses suit beginners, while expert riders can request a longer ride. Afterward, tour an old estate, cellars, and vinsantaia, then enjoy pecorino, cured meats, bruschetta, olive oil, and four Chianti and Super Tuscan wines.

“Our tour of the Tuscany vineyards on horseback was an experience I will never forget. The views were breathtaking, absolutely book this tour if you are considering it. Transportation to and from Florence was seamless, and our guides were extremely helpful. None of us had much experience riding horses, but felt extremely comfortable the entire ride. You can book a longer tour if you are more comfortable with riding upon request. The tours are private, which was much appreciated. Our tour was an hour and we finished the day at a vineyard overlooking yet another spectacular view of the region, sipping on incredible wines and indulging on delicious charcuterie. Book…”

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4.Florence: Horseback Riding Tour with Wine Tasting & Transfer

★★★★★★★★★★5.0 · 30 reviews · 3 hours · from $176Best value

Leave Florence with a small group of up to six, meet your horse at Crazy Horse Ranch, and practice with guides before riding through vineyards, olive groves, and country roads. Riccardo and Graziella help beginners feel secure, then take you to a historic wine estate for cellar and museum visits, four local wines, and selected cheeses.

“Our trip to Crazy Horse Ranch was amazing! The landscape is breathtaking and the horses are gentle and friendly, perfect for beginners. Amazing way to see the Tuscan countryside. We had a great conversation with Graziella and all the staff were really friendly and welcoming. The visit to the wine estate was the cherry on the cake, beautiful castle and great selection of wines! Special thanks to Graziella for making us feel so welcome.”

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