Horse riding holidays in Italy

Rolling Tuscan hills, Sicilian coastlines, medieval villages and vineyards

Horse Riding Holidays in Italy

Italy is a treasure trove for riders: rolling Tuscan hills, dramatic Sicilian coastlines, medieval villages, vineyards, olive groves, ancient forests and rich cultural traditions. It’s a horse riding holiday destination where scenery, history, food and adventure blend into one unforgettable journey.

Across Italy, riders can explore world-famous landscapes on horseback, from Tuscany’s postcard-perfect countryside to Sicily’s rugged mountains, volcanic trails and turquoise shores. Think long canters through open farmland, peaceful rides between vineyards, and centuries of history under your horse’s hooves.

The horses you’ll ride in Italy are surefooted, responsive and well-trained, making Italy an ideal destination for beginner, intermediate and advanced riders. Add in Italy’s legendary cuisine, boutique agriturismos, warm hospitality and expert guides, and this passionate nation delivers world-class horseback riding tours unlike anywhere else.

At a Glance

Best time to ride

February to November

Most popular regions

Tuscany, Sicily (fly into Rome, Florence or Palermo)

Riding level

Beginners through to advanced riders

Average temperature

18°C – 30°C / 64°F – 86°F

Holiday styles

Point-to-point journeys, luxury stays, food and wine experiences, cultural riding tours

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Italy

Sicily

Strong Intermediate Advanced
Next ride: 4 Apr - 11 Apr, 2026
From €1,9407 nights
Exclusive to Globetrotting

Italy

Tuscany

Beginner Intermediate Strong Intermediate Advanced
Next ride: 3 Mar - 7 Mar, 2026
From €2,0903 nights

Why Ride in Italy

Iconic & Diverse Riding Landscapes

From Tuscany’s rolling hills, vineyards, cypress-lined lanes and medieval hamlets to Sicily’s volcanic landscapes, coastal tracks and ancient forests.

Rich Equestrian Heritage

Italy’s connection to horses goes back thousands of years. Riders can explore bridle paths shaped by Roman roads, feudal estates and traditional rural farming culture, and authentically Italian.

Food, Wine & Slow Living

Italy is the ultimate destination for travellers who love to ride and indulge. Think long days in the saddle followed by fresh pasta, regional wines, artisanal cheeses and farm-to-table feasts.

Tailored Riding for All Levels

Whether you love relaxed countryside meanders, beach canters or wine-country treks, Italy’s expert guides customise each day to match your pace, ability and comfort level.

Banff Border Ride, Alberta, Canada

Kristy B.

5 months ago

‘Visiting Canada for the very first time was an absolute dream! Coming all the way from Australia, I was blown away by the sheer beauty of the Canadian Rockies and the chance to experience authentic cowboy culture firsthand. Riding out each day with our incredible guide, Ben, made me feel completely at ease – he knew the land, the horses, and the history so well. We saw wildlife everywhere, from elk to eagles, and every ride felt like stepping into a postcard. Adding in the Calgary Stampede at the start of my trip and an exhilarating rafting adventure, this was more than just a holiday, it was an unforgettable adventure that I’ll treasure forever.’

Banff Border Ride, Alberta, Canada
Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays

Kara K.

5 months ago

‘The Scottish Borders ride was my first Globetrotting trip. The planning and communication leading up to the trip were excellent. The horses are absolutely stunning and well cared for; they ride great and are anything but trail horses. Gemma does a great job matching you with a horse who suits you best. These horses are athletes and one of a kind. I think everyone in my group wanted to bring at least one of the horses they rode back home. The hacks are great, and the common rides are unlike anything I’ve ever done! They’re fast-paced, exhilarating, and not for the faint of heart. I highly recommend this trip for experienced and confident riders not looking for a run-of-the-mill relaxing trail ride. It was an honour to take part in such a historic ride, and it was great to see the Borders region of Scotland in a traditional way. It was an experience unlike any other! Accommodations were also top-notch, and I would definitely return!’

Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays

Karolina C.

5 months ago

‘I had an amazing experience at the Trans Wales Trail! Fun and friendly people, super fit and keen horses, plenty of tea and cake, and absolutely breathtaking views. This trip really touched my soul, as tears of pure joy streamed down my face while cantering wildly on top of a remote mountain range in the rain. Oh, and the horses! They were fierce and fabulous. My horse, Georgia, was a spicy little firecracker; she was such a fun horse to ride. I really recommend this trip for anyone looking for a fast ride with lots of freedom!’

The Maasai Mara Ride, Kenya

Kathleen H

5 months ago • Australia

1 ride with Globetrotting

‘I have just returned from the Maasai Mara ride in Kenya. We saw so much wildlife, both in numbers and species. This was my 3rd trip to Africa, and I had my first wild rhino sighting. We were treated to all of the big five during our week. The camps, although rustic, were very comfortable and quite a special experience. The food was delicious and plentiful, as was the drink! We met amazing new friends and loved every one of the staff! I can’t recommend this ride highly enough. If you want to experience Africa in a special way and create memories that will last a lifetime, this is the ride for you!’

The Maasai Mara Ride, Kenya
Kathleen H Australia 1 ride with Globetrotting
Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays

Kerry H.

5 months ago

‘I had an absolutely amazing week on the Scottish Borders ride. I rode 4 lovely horses who knew their job and were in great, fit condition. My daughter was also riding, and my husband came as a non-rider. He kept himself busy getting across the countryside, taking photos and videos of us all riding, which was greatly appreciated by the whole group. The common rides were great fun and very special to be a part of. The accommodation at Cringletie House was exceptional, and our mini Highland Games were so much fun! I would totally recommend this ride to any confident rider; I enjoyed every second!’

Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays
Helena, Montana

Kim K.

5 months ago

‘I loved the Helena, Montana ride; it had a little bit of everything. The horses were amazing, as were the staff and the facilities. To be able to ride out into the mountains and come home every day to a swim in the creek and enjoy a wine on the porch was a perfect balance of adventure and relaxation. All the staff were amazing, super friendly and helpful. The two daughters of Patty are amazing with their horses and are extremely skilled horsewomen, as is Patty. I rode Odyssey, who was perfectly matched to me. He was very responsive when I asked him to be, didn’t try to take off when not asked; he was the perfect gentleman. I would definitely request him again if I returned. I can highly recommend this ride. Thank you!’

Helena, Montana
Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays

Laura S.

5 months ago

‘The Scottish Borders Ride featured fantastic horses, a beautiful place to stay with great food, and amazing scenery, plus a huge dash of history thrown in. I love Scotland; it was so much fun. I had a fabulous experience at Cringletie House. The rooms were super nice, the staff were very helpful, and the meals were amazing. I love that place. All meals were excellent, and the Scottish dinner was fabulous. I rode Churchill, Sky, and Ramble; they were excellent. I really loved Ramble for the common ride; he was so comfortable. Gemma, our guide, did a fantastic job. She is amazing. I don’t know how she gets all those horses braided and ready. (Speaking of one professional to another: great job!) My favourite day was the border ride, which is just so beautiful. Participating in the common rides was unbelievable. Did I say I love Scotland? It was lovely to have time to explore the area around Peebles and enjoy the wonderful rides. Perfect!.’

Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays
Castle & Estate, Ireland, Globetrotting Horse Riding Holidays

Lindsay T.

5 months ago

‘I was a little nervous about going on a horse riding holiday as I’d only ridden in a riding school over recent years. I was filled with worries about my slightly novice canter holding me or the group back, or whether the horses would be gentle and responsive! Well, I shouldn’t have worried. I absolutely loved it! I could do a lot more than I realised; my confidence has improved dramatically, and it was so much fun. I rode a gorgeous boy (Henry) through stunning countryside with a bunch of other friendly riders, relaxed over 5-course evening meals, and had a lot of laughs. I’ll be booking a return trip!’

Castle & Estate, Ireland, Globetrotting Horse Riding Holidays
Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays

Lorraine S.

5 months ago

‘Riding the Scottish Border Rides will change your life; it changed mine! To be able to ride along with 200 local riders is unbelievable! To experience Scottish weather—how fun! We truly had one day of all 4 seasons in one day; it was great! Globetrotting does a terrific job with all the preparation suggestions, full details of the rides, and provides top-notch accommodations at Cringletie Estate. The horses, oh my! The best horses I have ever ridden in my life, and I have been riding my entire life. Every horse is more perfect and beautiful than the next! I still dream about riding them. My husband and I can’t wait to do another ride in Scotland and on Susy’s horses!

Scottish Borders Ride, Scotland, Globetrotting Horse Riding Holidays
Castle & Estate, Ireland, Globetrotting Horse Riding Holidays

Lucia T.

5 months ago

‘I loved this riding trip so much. I never jumped before in my life, and here I had the chance to learn the basics and try them out in nature. I felt a lot of support and encouragement from the trainers, and I could absolutely rely on and trust all the horses. The trainers were very experienced and dedicated to everyone, caring for everyone’s personal improvement. I was scared to jump at the beginning, but with their help and preparation, I found the courage, and now I am addicted! I loved the fact that we stayed right above the stables and could peek out to see the heads of a few horses at all times. The estate is huge and charming, with lots of trails and around 300 or so country jumps, so we had a wide choice of what we would jump every day. I just could not get enough at the end of the trip and would stay another week. Once you try it, you cannot stop jumping.’

Castle & Estate, Ireland, Globetrotting Horse Riding Holidays