This winter, I want to do something different with the family that’s a little more adventurous than lolling on the beach in Anguilla or downhilling at Beaver Creek. We’re not very sporty, mind you, but we do like the occasional hike. Every travel agent tells me that all the great warm-weather destinations are already booked …

A Family-Minded Adventure Seeker

I’m with you on the Caribbean. And while you would never call me an adventure-travel fanatic, I occasionally like to move beyond my comfort zone. How do I decide among all the new and wonderful places to go? Gray & Co. is hands down the most experienced adventure authority in my little black book; the company specializes in families and small groups. I would trust founder Cari Gray with the life of my firstborn—and, in fact, I have. It was Gray herself who took me and my then 13-year-old son hiking through the tea plantations outside Beijing. On that same trip, she arranged for Zachary to play basketball with a high-school team in Xi’an after our private viewing of the famous Xi’an terra-cotta warriors. There was also a three-day biking sojourn through Provence with my wife, where our days inevitably ended at wonderful châteaus and vineyards that weren’t in guidebooks. For a decade now, she has been in charge of active trips all over the world for power players like Tom Brokaw and financier Herbert Allen III. Gray & Co. is ideal for family, friends, and small, like-minded groups. I have given Cari’s name and private phone number (416-998-4082) to my closest friends. Enough said?

Hand of the Desert, the symbol of Atacama Desert, in Chile.

Come the end of October, Gray’s advice is to give the Peloton, your trainer, the treadmill, and the Caribbean a break. Head to South America to bike, paddle, and explore without jet lag. Right now, Chile, Uruguay, and Argentina are the places to be, as those countries are in the thick of spring and summer from November through April. The food is great, and the same goes for the hotels. But act fast. “The great places, even in South America, are well on their way to being booked through the spring,” warns Gray.

If it were up to Gray, she would send you to all three countries over the course of two weeks in one seamless, extravagant itinerary of jaw-dropping waterfalls, amazing wines, desert landscapes, days-end massages, and glorious candlelit dinners in the middle of nowhere. But that involves a very ambitious agenda—both financially and time-wise—that only Gray & Co. could manage.

The Singular Santiago Lastarria Hotel is located in the heart of the city.

Let’s start with Chile. The first stop for any Chilean adventure is Santiago. Be happy and stay at the Singular—a centrally located boutique hotel with a downtown vibe. The next morning, catch a two-hour Latam Airlines flight to Calama and head into the Atacama Desert. Spend your days hiking in cactus forests and lunar-like landscapes, swimming in salt lakes, and soaking in hot springs, admiring thousands of flamingos and geysers along the way. Check into Tierra Atacama, Explora, or the amazing Awasi Atacama, and give yourself at least three to five nights in order to adapt to the Aspen-like altitude.

The spectacular surroundings at Vik Chile.

If you prefer to stay at sea level and avoid issues of altitude altogether, there’s another alternative in the heart of Chilean wine country that’s only two hours by car from Santiago. The spectacular Vik Chile is so cool, so modern, so unlike anything else—the wine and food are wonderful, and you’ll wish all hotels could be so superbly run.

A relaxing guest room at &Beyond Vira Vira Hotel.

Further south is the Chilean Lake District, where the &Beyond Vira Vira Hotel is the ideal base camp for a few days of fly-fishing, volcano hiking, and spectacular scenery. Nearby, Tierra Chiloé Adventure and Spa Hotel on the island of Chiloé is known for fjords, ancient wooden Jesuit churches (now UNESCO-preserved), rain forests, marine life, and biking.

A pool with a view at the Singular Hotel Patagonia.

Patagonia, a region shared by both Chile and Argentina, is probably the Golden Fleece for many would-be adventurists, and it’s only about a two-hour flight from Santiago. The Singular Hotel Patagonia near Punta Arenas is a distant neighbor to Awasi’s stunning high-end retreat overlooking rocky Torres del Paine National Park. Expect roaming pumas, bubbling outdoor hot tubs, and the best naturalist guides in the business. A far cry from what you’ll find this winter at either Anguilla or Beaver Creek.

Richard David Story is a veteran travel writer and editor based in New York