Apparel FAQ Gear Riding

Packing for Paradise: What to Wear Horse Riding on Vacation

Written by Stephanie S.

“It’s ride o’clock somewhere!” Our fashion guide ensures you look (and feel) the part on your horse riding vacation.

Flights and hotel are booked. Time is running short, and your vacation itinerary is nearly complete. What could possibly make your trip better? The chance to go horseback riding while on vacation! There is no better way to explore a new place than between the ears of a horse, as they let you experience places in a way most people rarely do.

Wearing the appropriate apparel while horseback riding is critical for safety, comfort, and enjoying the entire experience. If you do not usually ride at home, you can still make this a fun and low-stress experience with some planning and preparation.

Horseback riding on vacation will create memories that last a lifetime, whether you are galloping a horse down a pristine beach or exploring mountainous trails that few people ever see on foot. So, dig out that suitcase, open those drawers, and let’s get to work! 

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The Essentials

As with any activity, there are some essentials that you must have prior to your equestrian vacation. These will assure that you can enjoy your ride with comfort and confidence.

Closed toe shoes with a heel

You must wear closed toe shoes to protect your feet in case the horse steps on you. In addition, heels on your boots prevent your foot from sliding through the stirrup if you have an “unplanned dismount.”

If you don’t want to get your current heeled shoes messy, check out our top boot picks here. You’ll find riding boots for every budget (and suitcase size!) on the list.

Long pants

The reason most photos you see of people out riding shows them in long pants is because the stirrup leathers (the piece of leather that attaches the stirrup to the saddle), and other parts of the saddle can rub against your skin and cause saddle sores if your legs are not covered. 

Jeans are a popular choice for riding, as are breeches and riding tights. You can also wear any long pants that are not slippery and do not have too much extra fabric. (Extra folds in the fabric can also cause saddle sores.)

Skip the jeans and go for a lighter fabric and/or ventilated riding tight if you are riding on the beach!


If you are not a regular rider, you probably do not have a riding helmet.

If you do have one, you might assume it’ll take up a lot of space in a suitcase. Not true! Simply turn your helmet upside down and pack smaller items like socks and underwear inside it.

The guide you are riding with may have helmets available onsite, but don’t assume they will — or that used helmets will be in good condition. Safety first will ensure that you have a fabulous time horseback riding.

(Check the Horse Rookie Amazon Must Haves List for helmet recommendations.)

Water Bottle

Stay hydrated. Water bottle holders for saddles are inexpensive, easy to pack, and can be adapted for other uses during your trip and when you get home.

(Bring your own water for the ride, too. Not all guides provide it.)


Knowing what to wear horseback riding on vacation helps you stay safe and comfortable.

Optional, but Encouraged

Once you have all of the essentials, there are a few other items that will make your ride even better.


A horseback riding experience on vacation is unforgettable

Your outfitter may have other recommendations for you, so ask them for advice before you pack.

Cell phone holder

You may want a cell phone holder to keep your phone at-hand for selfies and to decrease the chance it’ll bounce out of your pocket or bag during the ride. (#rookiemistake)

If you already have a phone holster for running or another outdoor activity, it should work well for riding.

We recommend one that attaches to your arm or waist so your phone is easily accessible. Or, grab this cell phone leg holster made specifically for equestrians.

(Chief Rookie Aside: I own two because they’re so convenient, secure, and easy to reach while riding.)

Phone holders can also be used for keys or other valuable items. 


If you have a pair of sunglasses with a strap, you enjoy the scenery instead of spending your time squinting into the sun!

Long sleeve shirt 

If you are riding in the woods, a long sleeve shirt can help protect your shoulders and arms from prickers, being scratched by trees, and biting insects.

If you’re riding on the beach or in the desert, a long sleeve shirt will protect you from the sun… and terrible tan lines.

Wear sunscreen, too!

Bug spray

Consider insect repellant if you’re going to be in the woods or a tropical location during the height of bug season.

Few things can ruin your ride faster than a swarm of mosquitos…

Horse Sense


Learn the basics before you go

If you are not familiar with horses, listen to your guide. Guides have years of experience with horses and are there to help you learn and have a great time.

Before you mount up and head out on the trail, your guide will give basic instructions, including how to steer, slow down, and stop your horse. Listen carefully!

If you do not understand something, ask for clarification. Take a few minutes to practice before you head out.

“A good horse is never a bad color.” 

It’s tempting to ask for the pretty horse, or the one that looks like the horse you have always dreamed of riding.

However, horses have distinct personalities, just like we do, and your guide knows the personalities of the horses well. They match horses and riders every day, so take the horse they suggest you ride.

If you do not feel that it is a good fit skill-wise while warming up or out on the trail, talk to your guide about switching.

Stay in your dance space.

It is tempting to want to bunch up next to your family and friends and ride close together so that you can talk. Remember your horse has its own personal space bubble, and there are pecking orders in horse herds.

If you get your horse too close to another one that is dominant over your horse, you could end up having your horse (or you) kicked or bitten.

A good rule of thumb is to keep one horse length in front and behind you to maintain harmony in the herd. It also gives you a chance to see the trail in front of you and avoid any trail hazards.

Relax and enjoy the ride.

Equines are prey animals and incredibly sensitive to the feelings and emotions of horses (and people) around them. It’s a survival instinct. They are especially in-tune with their riders.

Take a deep breath, look around at the scenery, and help your horse enjoy the ride too!

(Feeling nervous? Read our 32 tips for calming keeping your anxiety in check in the saddle.)

Frequently Asked Questions

What are the best horseback riding vacations?

With so many to choose from, you can create your own bucket list of horseback riding vacations. If you have a dream vacation, that is the best place to go.

If you need inspiration, look to well-known travelers such as Darley Newman of Equitrekking, or find the bucket list of another equestrian destinations.

Locations can be in North America or abroad, and there is something for everyone.

What should you wear horseback riding in the winter?

Layer up! Start with a base layer (not cotton) that will wick away moisture if you get wet or sweaty. Wool is an excellent base layer.

The trick to staying warm in the saddle is having clothing that will trap air. The trapped air keeps you warm, for example, fleece is an excellent option. Make sure you have warm socks, and gloves that will still let you hold the reins.

Fleece lined jeans or long underwear under your jeans will help keep your legs warm.

Slim hats can be worn under a helmet.

Read more about what to wear riding in the winter.

What should you wear horseback riding in Costa Rica?

Sunscreen! We are only half kidding.

You need to remember to protect your skin when you are out riding, the same as you would during any other outdoor activity.

As with any beach ride, be sure you are wearing clothes that you do not mind getting wet, and that can dry quickly. If you’re riding through the rain forests of Costa Rica, a light jacket and long pants are recommended.

Read more about what to wear riding in the summer.

What should you wear horseback riding in Hawaii?

We are going to start with what not to wear. Save that beautiful Hawaiian shirt you bought for another occasion.

Once you start riding at a pace faster than a walk, it will flap in the wind, and could potentially spook your horse. Wear clothing that is more form fitting for your ride, and will not flap.

If the terrain on your ride varies, you may want a light jacket (full zip, not one that needs to go over your head) so that you can take it off in the warmer locations and tie it around your waist.

Read more about what to wear riding in the summer.

What should you wear horseback riding in Jamaica?

Again, consider a hat, or a helmet brim to keep the sun off of your face. If you are riding in Jamaica, you are going to want to wear your swimsuit so you can fully enjoy the beautiful blue water.

For ladies, a pair of athletic shorts over your swimsuit will be more comfortable.

Talk to your outfitter ahead of time, and they will let you know the best options, but in most cases, you will be swimming with a horse for a good portion of your ride.

Read more about what to wear riding in the summer.

What should you wear horseback riding on a dude ranch?

Pull out the jeans and cowboy boots! Jeans are thick and will offer better protection for your legs from prickers and other hazards.

You might consider tying a bandana around your neck, or wearing a buff. These serve several purposes, including covering your nose and mouth if it is really dusty, and as a cloth to wipe sweat and any debris off of your face and away from your eyes while you’re riding.

Wear a helmet with a brim to keep the sun off of your face, or pack an attachable helmet sun visor for more protection.

A cowboy hat is fine for rest stops and picnic lunches, but it offers zero protection for your head in the event of a fall.  

Read more about what to wear riding on a trail ride.

What should you wear horseback riding on the beach?

Congratulations! Every equestrian dreams of riding horses on the beach, and you will soon be the envy of your friends.

On a beach ride, you will want comfortable clothing that will dry quickly if wet. Jeans are not recommended for riding on the beach. Many riders wear shorts, but call your guide or outfitter first to make sure that the saddles or other tack they use will not cause a saddle sore if you ride in shorts.

Use a sport top that will dry quickly, no cotton. Some prefer to wear their bathing suit under comfortable clothes.

Read more about what to wear riding in the summer.

In Summary

Horseback riding on vacation is one of the best adventures and will create lasting memories you’ll cherish. Before you know it, finding a local barn will be a required element for all of your vacations.

There are a few must-haves before you saddle up! Closed-toe shoes with heels are a no-brainer for safety, and trust me, it’s for good reason. If you’ve got your favorite pair already, that’s awesome. But if they’re too precious, check out their top boot picks. And yeah, when you’re out there riding, long pants are your best friends. You want to avoid those saddle sores – not fun!

Now, here’s a no-compromise rule: your helmet! It might seem like a space-eater in your luggage, but flip it upside down and stash some smaller items in there. Safety always comes first, and don’t worry, you can find helmet recommendations right here.

Stay hydrated – and that doesn’t just mean your horse! Bring your own water and get a water bottle holder for your saddle. You don’t want to be parched out there, trust me.

There are also some cool ‘optional but encouraged’ items to add more enjoyment to your ride. From cell phone holders to sunglasses, it’s about comfort and enjoying every moment. And speaking of comfort, a long-sleeve shirt might just be the saving grace on the trail!

Then, there’s the ‘horse sense’ part. Listen up and learn before you start – it’s the key to a smooth ride. Remember, horses have their own personal space, so don’t cramp their style. Oh, and relax – your calm vibe rubs off on your horse, seriously!

And the FAQ section? It’s a gold mine of tips about riding in different places, from Hawaii to dude ranches. So, grab these essentials, dress right, learn a bit, and get set for a ride full of memories! Let the adventure begin!”

Shop Horse Rookie Riding Essentials

Happy trails (or beaches)!

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Additional Reading & References

Beach Horseback Riding Tips
Caribbean Horseback Rides Take You Off The Beach and Into the Water
Horseback Riding Tours in Jamaica
What Not To Wear On Your Horse Riding Vacation

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About the author


Stephanie S.

When I'm not writing how-to guides for equestrians or researching new blog topics, I'm working my day job at a university or riding my Morgan Horse Remi. My work has also been featured in Equus, Holistic Horse, Equine Journal, and Equitrekking.