A riding vacation can be a lot of fun. But first, you should think about what you really enjoy in a vacation. Do you want tropical temperatures? Great views? Fast pace? Fancy accommodations? A particular breed of horse? Lots of non-horsey options for your family?

Galloping on Rossbeigh Beach, Ring of Kerry Trail Ride in Ireland

Riding Skills
Next, you should honestly evaluate your riding skills. As we all learn at some point, "the more you know, the less you know". You should be very clear and honest with yourself about your skills when you sign up for a trip. Avoid summing it up with a phrase like "advanced rider"; give specific details about your riding history. Have you ridden for two years or thirty? Do you ride once a week in a ring on a school horse or do you own 10 horses and do weekend camping trips? All variations are fine to enjoy a riding vacation, but the guide must know which horse would suit you best to make you AND the horse happy. This also means you have to be honest with your weight as well. It's fair to the guide to stay within 10 years and 10 pounds. Being honest means a 4' 10" woman that prefers a quiet horse doesn't end up on a 16.3 hh draft cross that loves to gallop.

Riding Style
Another key point is whether you ride English or Western, and if you're willing to try something new. Few of the trail rides have jumping, and if they do, they would have a "go-around"; so even if you ride English, you don't have to worry about leaving the ground unless you want to. Remember that taking a vacation means opening yourself up to new experiences, scents, tastes and cultures, so riding in a different type of saddle, especially if it's the local style, can be part of the fun. Of course a few lessons before you go may be just the confidence boost you need if it'll be a new riding style for you. Also keep in mind that you should make it clear if you're afraid of heights, cannot live without air conditioning or have special dietary requirements. These types of details are key factors in choosing a vacation that will please you best.

Be Flexible
Bear in mind that all trips may not have all the options you're looking for, so you should be willing to compromise and decide which one or two factors are the most important for you. And consider that you're riding horses that live in the countryside, so accommodations will lean towards guesthouses and B&Bs. Fancy hotels tend to be located in cities, where horses aren't much fun to ride. There are 5 star resorts that also have equestrian packages, but generally offer lessons and rarely have trail riding.

Viewing the Hippo on the Big 5 Safari ride in Africa

Another factor to consider is when you can travel. If you're a teacher, for instance, and can only take a vacation in the summer, you'll have to deal with higher flight costs and more sold out dates. If you're more flexible but want to see the peak of lavender in France, then you would have to go from late June to early July. Obviously this is not a very big window. The rainy season in Costa Rica is August to the end of October, so you can't ride when the rivers and roads are flooded. But right after that, the fields, trees and flowers are at their most lush and beautiful.

Since you'll be in an area you may not have visited before (yes, this could be the west coast instead of the east, or India instead of Indiana), you should be gracious to your host and try new things. If you don't eat meat and dinner is a BBQ, for instance, explain your dietary habits quietly and don't make a big deal of local traditions that don't conform to your beliefs. If they drink tea with whiskey, try a sip for fun. I was willing to try a pastis in France and found it wasn't to my liking, so I shared it with another rider. If the only toilet facility is an outhouse, well, that is just part of the adventure! Some of your best stories back home will come from the new things you experience while traveling.

Ask When Necessary
When on the trip, don't be shy — ask the guide for anything you might need. They can't help if they don't know. A band-aid, tampon, extra crackers, or something for an upset tummy are all reasonable requests. Even a different horse if you're unhappy. The guides do an incredible job matching horse to rider (when you're honest with your experience level), but are also happy to change to make sure you're having a good time.

Packing
You should pack for the climate, and bring layers. Don't go crazy with fancy outfits, find out if even one is necessary, and if so, bring just that one. Your luggage will have to be transported by staff each night, so they appreciate it if you don't over pack. You should also not get carried away with jewelry, laptop, cell phone or video camera. Anything that is left in the luggage has the potential to be stolen. Not that this happens often, but why take the chance? If you bring a camera along for the ride, figure out how you can carry it without damage. A small fanny pack with a washcloth to pad it might work fine, or sometimes the guide will supply saddle bags — but find out before you go. And in either instance, you should bring along plastic bags in case it rains.

For riding, just two to three pairs of riding pants are enough for the week. Paddock boots with half chaps are the most comfortable for the trail and the easiest to pack — some riders wear their boots right on the plane! You will need all your toiletries, as pharmacies are few and far between, and you won't be likely to find your favorite brand. Also remember that you may not have internet access in rural areas, and you need a special plan if you want to use your cell phone overseas. It's easier to buy a calling card to use while you travel. But this is vacation after all — leave the emails, Facebook and Twitter until you return home — vacation is time to relax and unwind.

Monkey Puzzle Trees on the Pioneers of Patagonia Ride in Argentina

Lots to Choose From
The good news is that the horseback riding companies that offer a variety of trips will be able to help you with all these options. They can take your skills and desires and give you a few perfect choices so that you can experience the vacation of a lifetime. Of course, once you've tried one, you'll be very tempted to try another!

Lynn Webb is President of Hoofbeats International, an enterprise offering riding vacations around the world.