Meticulously equipped for every conceivable discipline of horsemanship, the sprawling Equestrian School at the Gleneagles (the surrounding trail network included) offers the riding world’s equivalent of an Ivy League education. Or at least a quickie version thereof; few guests stay more than a week. Extracurricular activities include spa-going, biking, loch-hopping and dignitary-spotting.

For more information: The Gleneagles

By day, trot through nature sanctuaries, tribal villages and sheep-induced traffic; by night, trot out your best maharaja impression. Most accommodations are classic heritage hotels—converted forts, palaces and rawlas (“small mansions of erstwhile nobility”) still owned by Indian aristocracy.

For more information: Ghanerao Safari Tours

With the eco-posh Urubamba Villas as your home base, you’ll take daily rides through the Sacred Valley of the Incas, where—if you head up-mountain in almost any direction—you hit the 17th century in about 45 minutes (think: ruins, agrarian villages and an exceptionally high llama-to-human ratio). Of course, the guides (who, together with your housekeeper/chef, make up your staff for the trip) will keep you on track.

For more information: Inkaterra Custom Equestrian Tours

With the eco-posh Urubamba Villas as your home base, you’ll take daily rides through the Sacred Valley of the Incas, where—if you head up-mountain in almost any direction—you hit the 17th century in about 45 minutes (think: ruins, agrarian villages and an exceptionally high llama-to-human ratio). Of course, the guides (who, together with your housekeeper/chef, make up your staff for the trip) will keep you on track.

For more information: Inkaterra Custom Equestrian Tours

Its 10-million-euro renovation scheduled to debut right about now, the resident Equestrian Centre and Hunting Lodge boast—among other claims to fame—the Virtual Horse (Ireland’s first full-sized, simulated steed), 300 new jumps built by Wilson Bros. (the Nicklaus and Fazio of horse courses) and 21 miles of scenery-saturated bridleways. The castle itself has been remodeled, too, and reopens in June as a members-only retreat (but you can become a member for 3,000 euros a year, helipad use included).

For more information: Castle Leslie Estate

These are custom-designed, with options ranging from a sprinkling of horseback rides to exclusively equestrian safaris. And while the location is negotiable as well, some of the best places for horseback game-gazing are in East Africa: Ol Malo, Lewa Downs, Singita and Grumeti, to name a few. Micato can also arrange for you to play polo (a popular sport in Kenya and Tanzania).

For more information: Micato Horseback Safaris

On rides of two to four days, you’ll reenact parts of the Corps of Discovery expedition (had it involved feather beds in pre-pitched tents and multi-course meals on the impeccably set tables, of course). And we’re pretty sure Lewis and Clark didn’t wind down with the Apres Adventure Couples Massage or the Four Paws Double Therapist Massage, but either treatment is a great way to reenter “civilization” (i.e., the Paws Up wilderness lodge) post-pack trip.

For more information: Paws Up Outfitters

A glorious example of conspicuous consumption, this valley is filled with centuries-old, outsized, wealth-heralding chateaux. Even the backdrop—a blend of sunflower fields, vineyards, forests and rolling hills—is immodest. What to do with all this brazen beauty? Ride through slowly, pausing for winery breaks, riverside picnics and butler-orchestrated massages.

For more information: Cross Country International’s Chateau-to-Chateau Trail

Sensory overload is a significant risk on this six-day ride: You’ll be surveying Mount Kenya, the Lewa Plains, the Ngare Ndare Forest and countless outsized representatives of the animal kingdom (giraffes, elephants and hartebeest, to name a few). But there’s also ample opportunity for mental palate cleansing—over poolside Pimms, say, or even better, an in-room massage.

For more information: Abercrombie & Kent Lodge-to-Lodge Ride

If you don’t play polo already, you may want to take it up for the improbability factor alone here: Sitting at the base of the Great Wall is an equestrian center-cum-polo grounds where you can participate in the sport of kings with one of their relatives. China’s Jordanian ambassador (part of the Hashemite Kingdom’s royal family, and the polo center’s self-appointed coach) will be happy to have you, and will adjust the teams—a rotating cast of local characters—accordingly. Between your Sunday and Wednesday games, canter alongside the Great Wall, sections of which can be reached only by riders (or exceptionally determined hikers).

For more information: Great Wall Kempinski