Where to Ride: the 15 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 $176

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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5.Scenic Horseback Ride, Wine Tasting & Lunch on Mt. Vesuvius

★★★★★★★★★★5.0 · 23 reviews · 4 hours (approx.) · from $138Best value

Ride a saddled horse through a Vesuvius vineyard, learn how volcanic soil shapes local grapes, then visit a local wine stop for regional products, charcuterie, cheeses, jams, honey, and dessert. Giuseppe can help first-time riders, while Sophia and her team handle tour communication. The experience lasts about four hours.

“Great communication from Sophia and her team. Horses were great, a really beautiful way to explore a winery!”

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6.3 Hour Horse Ride to a Castle for Wine Tasting and snack Lunch

★★★★★★★★★★5.0 · 9 reviews · 7 hours (approx.) · from $830

Ride 3 to 4 hours through the vineyards and olive groves of the Florentine hills with a horse guide, then visit a medieval wine estate for a Tuscan lunch and tasting of three to four wines. Simona and her team handle the private Florence transfers, while guides help riders of different skill levels.

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7.Horseback Riding on Mt. Vesuvius with Wine Tasting and Dinner

★★★★★★★★★★5.0 · 6 reviews · 4 hours 30 minutes (approx.) · from $170

Meet in Pompeii for a small-group horseback ride on Mount Vesuvius, followed by a traditional local meal and paired wine. Your guide provides helmets, riding support, food, and roundtrip transport from the meeting point. Groups are capped at eight, making this a relaxed choice for couples and first-time riders.

“This was mine and my husbands favourite part of our honeymoon. The horse riding was beautiful and the staff were very helpful, especially as I was a complete beginner! Our driver was so friendly and fun which made sure that every moment of this experience was memorable. Last and definitely not least, the food. The chef was fun, chatty and an excellent chef who made delicious food. The meal had paired wines which were also delicious. The views and settings were breathtaking. Overall this was excellent value for money and a completely unforgettable experience. Thank you!”

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8.Horseback riding and wine tasting

★★★★★★★★★★5.0 · 6 reviews · 4 hours (approx.) · from $190

Spend four hours riding for about 60 minutes through vineyards toward the Custoza hills, then visit a family-run winery for white, rosé, and red wines with cheese and salami. You’ll help prepare and groom your horse, learn basic riding commands, and enjoy this private English-language experience with only your party.

“Best experience of the whole trip. The horses were great and the winery was beautiful! The 3 wines that we sampled were the best we have ever had!! Hoping to order a case!!! Highly recommend doing this excursion. It will not disappoint!”

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9.Horseback Riding with Wine Tour from Florence

★★★★★★★★★★4.9 · 5 reviews · 7 hours · from $235

Leave Florence in an air-conditioned eight-seat minivan for a one-hour horseback ride through Chianti vineyards and olive groves. Visit San Gimignano, then enjoy a light Tuscan lunch with Chianti wine, balsamic vinegar, and extra-virgin olive oil tastings. English, Italian, and Spanish guides lead the day, with Lorenzo among the praised guides.

“Wycieczka cudowna, same atrakcje i lokalizacja jak z bajki ale przewodnik zrobił z tego tak świetne wspomnienie, którego na pewno nie zapomnę do końca życia!!!! Koszt wycieczki jest w 1000% adekwatny i nawet powiedziałabym że za niski jak na to co otrzymałyśmy. Polecam z całego serca”

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10.Verona: Horseback Riding and Wine Tasting Experience

★★★★★★★★★★5.0 · 5 reviews · from $186

Meet your horse, help saddle up, and learn basic riding skills before heading through the Custoza vineyards. At a family-run winery, taste white, rosé, and red wines with homemade cheese and salami, then return to brush and reward your horse. The small group has up to six people, with English and Italian guides.

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11.Horseback Riding with wine tasting in Lake Garda vineyards

★★★★★★★★★★5.0 · 3 reviews · 3 hours (approx.) · from $157

Ride for two hours through the vineyards, olive groves, forests, and country roads near Lazise and Castelnuovo del Garda. Your small group, capped at four, then stops at Tinelli Wines for three regional wines, water, cold cuts, and cheeses. Guides welcome beginners, and the tour runs in English from 9:30 am.

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12.Horse Riding Experience on Vesuvius w/ Wine Tasting

★★★★★★★★★★4.5 · 2 reviews · from $160

Spend four hours around Mount Vesuvius with an English-speaking instructor, one hour on horseback, and a wine tasting at a local estate. Ride among vineyards with views toward Capri and the Sorrento Coast, then enjoy four wines, food bites, lunch, a helmet, and roundtrip transport from Pompei. Groups are limited to six.

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13.Horseback Riding and Winery Lunch Experience in San Gimignano

★★★★★★★★★★5.0 · 2 reviews · 4 hours 30 minutes (approx.) · from $641

Meet at 9:00 am near Florence’s Piazza Adua for transport to a winery near San Gimignano. After a short riding lesson, spend about an hour on horseback through vineyards, woods, and old hill paths. Finish with a four-course Tuscan lunch, local wines, and a wine-pairing class before returning to Florence.

“Best experience we have ever had in Italy. Everything was so well organized and was incredibly fun. We felt very well cared for and loved each minute. Can’t recommend enough!”

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14.Wine tasting and horseback riding in Montepulciano, in Tuscany from Rome

★★★★★★★★★★5.0 · 2 reviews · from $503

Leave Rome by private vehicle for Tuscany, where you can ride gentle horses through vineyards, olive groves, and woods. Afterward, winemaker Alfredo leads a cellar visit and tasting of Nobile di Montepulciano, Vin Santo, and local foods. Beginners, children, and non-riders can be accommodated.

“This was the highlight of the trip! The horseback riding was magical and then we went to the city of Montepulciano. A castle on top of a huge mountain with shops and wine everywhere. And then the winery was unforgettable. The wine, the food, the view! You have to book this!”

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15.Tuscany: Horseback Riding Adventure with Lunch in a Winery

★★★★★★★★★★4.2 · 2 reviews · 4.5 hours · from $542

Meet your English-speaking guide near Florence Santa Maria Novella station, then ride for about an hour through San Gimignano vineyards, olive groves, woods, and cypress-lined roads. A four-course lunch follows at the winery, paired with local wines including Rosso and Brunello di Montalcino. Expect scenic views, basic riding instruction, and a firm, sometimes rocky route.

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