Story and photos by Shawn Hamilton

As a photojournalist specializing in horseback riding vacations, I’ve had the privilege of experiencing incredible opportunities that I will always cherish. Through my work, I've had the chance to explore hidden corners of the world that most tourists never see and connect with fascinating people from across the globe who share a passion for horses. In my view, there’s no better way to immerse yourself in a new culture than from the saddle of a native horse, taking in the sights, sounds, and scents of a place.

After the restrictions of the pandemic, many of us are eager to travel again, and if a horseback riding vacation is on your horizon, you may be wondering where to go. Choosing the right destination can feel overwhelming, but I’m here to offer a few tips to help you make the best decision.

The question of "Where should I go?" doesn’t have a one-size-fits-all answer. Several factors come into play when selecting the perfect riding vacation. Start by considering your budget, preferred amenities, your riding skill level, accommodation options, safety measures, and the quality of food. All of these aspects can make a big difference in crafting your ideal horseback adventure.

Unwinding at The Paradise Spa in Costa Rica.

What can I afford?  

To help understand the vast range of prices out there, remember that one factor governing what an outfitter charges is the number of services outside of their realm. Hotels, shuttles, meals, and activities off premises often have to be paid in advance and will affect the outfitter’s cost of accommodating you. A vacation with rides that take place on the outfitter’s own or permitted-use land, and that house and feed you on their own premises, will be much more affordable. If you’re on a tight budget, save on airfare by considering something close to home. Remember that COVID-19 restrictions may also limit you to your native country or demand a two-week isolation period. We all hope these constraints don’t last too much longer.

Related: Canada's Yukon on Horseback

Many outfitters will pick you up at the airport to transport you to their ranch, but if a rental car is needed to get to the location, ask for contact details for other guests to arrange sharing a vehicle. You have already paid for your four-legged transportation, so why pay more money to rent a vehicle that will only sit in the parking lot until you’re ready to go home? 

Where do I want to sleep? 

A well-rested body makes for a more enjoyable ride. If you are going to wake up every morning in pain from sleeping on the floor or on a cot in a tent, will you be comfortable in the saddle all day? Choose what works best for you. If you desire a luxury queen-size bed with fluffy pillows, then don’t sign up for a ten-day camping trip sleeping under the stars — perhaps glamping or a comfy cabin is more your style. Packing into remote locations where luxury accommodations are not available can reveal some spectacular scenery, yet I have experienced some breathtaking views not far from a luxurious, comfy cabin. Figure out what your body can handle. Your comfort is of utmost importance so you will enjoy your vacation.  

Camping on the Crossing of the Andes Ride from Chili to Argentina.

What amenities do I need? 

Not all rides provide flush toilets and hot showers. You may find yourself straddling a hole in the ground with nothing but a nylon screen flapping in the wind to keep your private parts from view. If you prefer privacy or luxury when on the throne, ask about the toilet facilities. I have experienced the full gambit of bathroom options, including flush toilets trailered into our glamping sight in India, with water delivered daily by camel. Some of the best views, however, have been from rustic outhouses in remote areas. 

Tents all in a row - glamping in India.

Hot showers are never a guarantee. If showers are a must in your daily ritual, be sure to ask in advance. 

A hot tub is not a necessity but is definitely a welcome perk — and it certainly adds to the experience if freshly made margaritas are on hand. But as long as it is clean, hot, and has jets to soothe aching joints after a long day in the saddle, it’s a bonus. I have even ventured into hot springs that looked a little questionably green. 

What do I want to eat? 

The shrimp-and-smoked-salmon cocktail prepared by Megan, a qualified chef and one of the wranglers at Hunter Valley Station in New Zealand.

From mutton soup and guinea-pig-on-a-stick to sipping Malbec wine at an Argentinean barbeque, the food possibilities are endless. What is your tolerance? Can the outfitter adapt to dietary restrictions? Food is an integral part of pleasing guests and most outfitters do their best to accommodate, but depending on where you are going, their delicacy may not be your cup of tea. If you are travelling from one location to another in a camp atmosphere, the food may be much more basic than in a five-star ranch dining room. On the other hand, I have had some excellent meals in the wilderness, including pizza made on an open fire. If you have food allergies be sure to contact the outfitter before you arrive. If you have a delicate system, remember to pack some Imodium.

Guinea-pig-on-a-stick at the local market in Aloag, Ecuador.

In some countries, meal intervals can be quite lengthy compared to your munching times at home. I recommend bringing some high protein snacks to keep in your saddlebags for a quick pick-me-up between meals. I also bring my own water bottle with a built-in filter system and prefer one that can be easily managed with one hand. 

What is my riding ability?  

Here, honesty is the best policy, and I cannot stress this enough. Being completely truthful about your riding ability and comfort level can make or break your trip. You will be on your mount the bulk of the day, so for the sake of your comfort provide all the information you can to the outfitter. A high-level rider ten years ago who hasn’t been in the saddle for some time is not an expert. Unused riding muscles will not enjoy a high energy or strong horse that jigs the whole time. A walk-trot rider who canters occasionally on a two-hour trail ride twice a week should NOT sign up for The Gobi Gallop in Mongolia.

Check the itineraries for the number of hours in the saddle. Are there rest periods at lunch to give your body a break? Or does the adventure of crossing the Andes or galloping 700 kilometres of the Mongolian desert outweigh the aches of long hours in the saddle? On the other hand, you may be disappointed that rides are too short. A day may be eight hours long but may include only two hours in the saddle. Most complaints I have heard from guests are that the rides are not long enough. I did, however, experience a 13-hour day once and believe me, it was long enough. Be honest with yourself and with the outfitter, and choose what’s best for you.

Related: My Riding Vacation at Wild Deuce's Women's Retreat

Another factor is the speed of the ride, which can range from a nose-to-tail walk all day to long gallops at a moment’s notice. Keep in mind that the ride has to cater to the least experienced in the group. If you are looking for an adventurous, vigorous ride make sure you are signed up for an advanced riders-only trek that does not allow beginners. This also works in the reverse. If you prefer a calmer ride, don’t sign up for an advanced rider version and force everyone else to slow down the pace. Again, be candid about your riding abilities, with both yourself and the agency or outfitter, so they can accommodate your needs.

Typically, rides that go off-property for several days will give you the first day at home to test your mount. If you are unhappy or uncomfortable with your mount for any reason, let the outfitter know. Outfitters are not mind readers; they can certainly tell if you can’t get your steed to pick up a trot or respond to your stopping and turning aids, but they cannot tell if you are uneasy about the dynamics of the horse they chose for you. Be sure to speak up early so the outfitter has time to resolve the situation before you venture too far from home.

For horses and tack, what will I be comfortable with physically and morally? 

In my experience, for the most part the tack has been good, but there have been exceptions. Look at the photos on the website, study the horses’ mood and the fit of the tack. Are the riders wearing helmets and proper footwear? Do your due diligence, check the website, talk to people who have been on the ride, and read the testimonials. If an outfitter asks your weight and has a maximum allowance, it’s a good indication that they care more about the horses than dollars, and will also consider the horses when it comes to tack. At my age, I just might consider bringing one of those comfy sheepskin saddle covers on my next trip, but will need to bring the correct one to fit the saddle I will be using. 

What do I want to see, do, and learn? 

Loving the hot tub at Rancho Las Cascadas in Mexico.

Why does this particular location appeal to you? Are you interested in the culture and history of the country? Do you want to learn team penning, square dancing, fly fishing, or the basics of natural horsemanship? Or do you want to go swimming with your horse? Maybe a retreat to find your inner self or a ride combined with yoga will suit you. Sometimes there are optional activities available in the area that the outfitter or agency can help you find, so look into the non-riding activities. 

A demonstration of how coffee is dried at a farm in Viñales Valley, Cuba.

Related: The Real Cuba - From the Saddle

Who will be guiding me?  

If your guide speaks your language, and is knowledgeable about the local history and flora and fauna, it will make for a much more entertaining trip. Ask about your guide’s language and knowledge of the area. Ask former guests about their experience. If they praise a certain guide, be sure to ask if that guide will be heading up your trip. 

Will I be safe? 

When looking at photos of rides on an outfitter’s website, watch for guides placed both at the front and back of the riding guests. Look for ratios of guide-to-guests. Did the outfitter or agency ask you about your medical insurance and who to call in case of an emergency? Do the bulk of the photos show riders wearing helmets or are they in running shoes with baseball caps? I always bring my own helmet, riding boots, and chaps. If you are uneasy about falling perhaps you would feel more comfortable in a safety vest. 

A cabana with a thatched roof and a bed with mosquito netting at Mountain Equestrian Trails in Belize. 

Should I book through an agency?

There are many agencies that specialize in horseback riding vacations all over the world. It is often easier to search through an agency’s website for itineraries and descriptions than to endlessly surf the internet for individual rides. The number one benefit of using an agency is that typically, but not always, one of the agency’s representatives has been on the ride previously. They check for things like amenities, tack, safety, guides, etc. It is often easier to ask the agency questions than trying to get in touch with an outfitter who may be out on the trail for days on end, and not all outfitters can afford to pay someone to sit in an office and answer the phone and email. An agent will most likely already have the answers to your questions. Agencies can also help you book your flight, arrange extra transportation, and can often get discounts for group accommodations and outings outside the ride. And if you are uncomfortable sending money directly to the outfitter in a foreign country, then I suggest you deal with an agency. Due diligence is needed with agencies too — look for testimonials and talk to others who have dealt with them.

Some outfitters are not represented by agencies and will only take on customers directly. Remember that agencies take a commission that usually comes out of the outfitter’s pocket.

There are many questions to ask yourself and your destination outfitter when planning a riding vacation. I hope this article will help you make the right choices. Personally, I am beyond eager to get out there and support the outfitters that I am sure have suffered during these hard times, and I encourage you to do the same once it’s safe and restrictions are lifted.

After you’ve asked all your questions and made your decision, remember that there will always be surprises. So, keep an open mind and bring a sense of humour along with your sense of adventure.

Click Here for my Checklist for a Comfortable Riding Vacation

Happy Trails!

Photojournalist Shawn Hamilton is eager for pandemic restrictions to ease so she can return to travelling the world in pursuit of adventures on horseback. She is pictured with a friend on the Fall Colors of Vermont Ride.

Related: South Algonquin Equestrian Trails

Related: The Land of the Long White Cloud Ride

Check out more Holidays on Horseback.

More by Shawn Hamilton

Main Photo: A river crossing on the day ride from Boundary Hut, New Zealand, on The Land of the Long White Cloud Ride with Wild Women Expeditions.