The World’s 4 Best Siena Horseback Riding Tours

1.Siena: Horseback Riding Tour in the Tuscany Countryside

★★★★★★★★★★4.8 · 321 reviews · 1 hour · from $82Our pick

Ride gentle, well-trained horses through the Tuscan countryside from Colle Pinzuto near Siena. Beginner instruction, helmets, and a small group of up to seven make this a relaxed introduction to riding. Guides such as Julio and Giulio lead you past vineyards, olive groves, rivers, and cypress-lined roads, with optional picnic and winery add-ons.

“My daughter and I had a great time riding even I've only done it once before. Julio was friendly. Only quivvle is that Google maps location may nee dto be updated as it didn't lead me close enough to the meeting location.”

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2.An Exclusive Horseback Experience in the Heart of Tuscany

★★★★★★★★★★4.8 · 221 reviews · 1 - 2.5 hours · from $82

Ride for about an hour through vineyards, olive groves, and Siena’s rolling countryside from Polo Club Villa a Sesta. Melissa and her team provide calm horses, helmets, boots, and patient instruction for riders aged 14 and up. Add a winery visit, farm stop, or homemade meal if available with your booking.

“We feel so lucky to have discovered this place - it’s now marked in both our memories and on our map. The horseback riding was truly amazing! The nature and views were breathtaking, but what touched us most was the entire journey of connecting with our horses Stella and Macchia. It was beautiful, grounding, and deeply emotional. When we returned to the farm, we were greeted by cheerful and adorable truffle-hunting dogs - such a fun and heartwarming welcome! We then had lunch at the owner’s house, prepared by the owner himself. He is a warm, open-hearted person, and his hospitality made us feel immediately at home. The food was…”

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3.Tuscan Chianti Hills Horseback Riding Tour

★★★★★★★★★★4.0 · 61 reviews · 1 hour 30 minutes (approx.) · from $90

Leave central Siena by minivan for a 60-minute guided ride through Chianti countryside. You’ll meet a horse matched to your ability, practice in the arena, then follow quiet roads, forests, villages, and sections of the Via Francigena. Guides including Aldo, Aladdin, and Musa have helped beginners feel at ease, though you should confirm pickup and meeting details before booking.

“Such a fun excursion!! Definitely book. There’s tons of horses for you to look at while you wait to start. The horses are pretty trained so if you’ve never ridden a horse before you’ll be fine. We also did this tour in July and it really wasn’t too hot. A lot of the trail is in the shade! Book it!”

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4.Horsebackriding – explore Tuscan nature

★★★★★★★★★★4.5 · 29 reviews · 3 hours (approx.) · from $102

Ride through the Crete Senesi and Val d'Arbia near Siena with Clara and her team. You’ll meet your horse, receive a basic safety briefing, then spend about 2 to 2.5 hours on quiet country routes. The standard ride is walk-only, suits first-time riders, and is limited to five people. Helmets and soft drinks are included.

“Book this now!!! This was a highlight of our 3 weeks in Italy. Clara was wonderful and so patient with our inexperience with horses. The views alone are worth booking this, but the horses were wonderful. We had a great time.”

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