Horse Riding Holidays: What No One Tells You Before You Book

Thinking of booking a horse riding holiday? Most guides tell you where to go. But few talk about the realities of spending 4 to 6 hours a day in the saddle — or what to wear under your breeches when you're halfway through a mountain trail and start to feel the burn (literally).

At My Riding Underwear, we design technical riding underwear specifically for long days on horseback — and we’ve heard everything from our community. Here’s what we’ve learned.

Choose the Right Type of Trip — Not Just the Destination

Most blogs list beautiful places: Tuscany, Alentejo, the Camargue… But before choosing your destination, ask this:

What kind of rider are you right now — and what kind of ride do you want?

🩲 The Most Forgotten (and Important) Piece of Gear: Underwear

Let’s talk about it — because most blogs won’t.

Long riding days can cause:

• Chafing in inner thighs and seat area
• Pressure points from seams
• Moisture build-up leading to irritation or rashes

Regular underwear wasn’t designed for 6-hour trail rides. Ours was.

• ✅ Discreet padding that protects your seat bones and inner thighs
• ✅ Breathable, seamless design to prevent rubbing
• ✅ Flat elastic to keep everything in place, no matter the movement

“I didn’t know padded underwear for riding existed. I’ll never go back.” – Feedback from our customers

🧳 Packing Tips From Riders Who've Been There

Forget Pinterest-perfect packing lists. Here’s what real riders say they wish they’d brought:

• 2 pairs of padded riding underwear (swap mid-trip for hygiene)
• Fast-drying riding tops — not just cotton
• Electrolytes or hydration tablets
• Zip-lock bag with Vaseline or anti-chafe balm
• Wide-brimmed helmet-friendly hat for off-horse time

Bonus: Always bring something to sit on at picnic stops. A folded bandana or mini seat pad works wonders.

Questions to Ask Before Booking (That No One Tells You)

Most booking sites won’t include these — but they matter:

• Are the horses barefoot or shod?
• Is there a rider weight limit?
• Can I bring my own saddle pad?
• Are toilet stops planned during long rides?
• Do they provide riding underwear or should I bring my own?

Do You Really Need to Go Abroad?

Not necessarily. Equestrian escapes exist in your own country and are often more accessible, affordable, and just as beautiful. Plus, you support local guides and horses.

Try searching for:

• "Horseback weekend getaway + [your country]"
• "Equestrian B&B"
• "Slow travel horse riding trips"

Gifting the Experience? Go the Extra Mile

If you're gifting someone a riding holiday, make it even more special with:

• A gift card for technical riding underwear
• A physical voucher for presentation
• Extras like a printed map or riding-themed postcard

Final Thoughts

Horse riding holidays offer more than just scenic views. They challenge your body, create new bonds with horses, and leave you with stories for life. But your comfort in the saddle can make or break the experience.

👉 Explore our padded underwear — made for real riders, tested on real trails.