Midnight in Havana. The ride from the airport stretches out in a kind of darkness not often found in a city of two million. A bleary series of doors open, spilling light over sleeping dogs, before slamming shut: Every casa familiar, Cuba’s equivalent of a hostel, is full. The last time I visited Cuba, in 2009, the idea of making a reservation was laughable. Now, U.S.-Cuban relations are thawing, and the driver jokes his country has become like Noah’s Ark. “The Americans are coming in pairs!”

Eventually, a nice couple from Colombia agree to share the floor of their room with me. In the morning, the sea sprays over the malecan, where teenagers drink off-brand Coke and play Taylor Swift, looking toward Miami. The port bustles with news of ferries arriving from the U.S. Vendors squabble over a spot to sell cigars to the influx of tourists. “Socialism o muerte,” proclaim the billboards. The city, like October leaves, is in a wispy in-between state, where you can see what has been but also what’s coming.

Outside of Havana, the contradictions grow. I’m headed to Viñales, a sleepy town on the country’s mountainous western tip, where flat-topped, sheer-sided, limestone cliffs tower over the country’s tobacco region. The magotes, as they’re known, used to provide shelter for runaway slaves; now, the mist-cloaked valley is one of the few places on the island where you’re allowed to hike without a guide. In these hills somewhere, there’s rumors of a healing spring, los Aquaticos, whose magical waters purportedly fix ailments of all kinds.

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The bus threads out of the city, past roaring 1950s Fords and aging Soviet Ladas till we reach the sleepy roads of Viñales, where a dirt path forks onto acres of tobacco fields, the young plants pushing out of the red earth. There’s several trails that slope up to meet the limestone cliffs, through a dim cave and out onto the other side, where rock climbers are scaling the wall. Viñales has world-class sport climbing, but locals’ lack of equipment and its far-flung location has so far kept the routes uncrowded.

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But in short order, I’m lost. In Cuba, there’s no Googling directions, no GPS coordinates, not even a map. This trail is not made for hikers; it’s the only access to dozens of tobacco farms, whose owners rely on it daily. Crossing the valley, the path splinters into dozens of intersections. The island holds some of the best outdoor adventures in the Caribbean-from amazingly pristine reefs to biking to sport climbing-but beyond Havana, traveling in Cuba can require some extra preparation. You should visit–and you should visit soon–but here are a few things that are helpful to know before you arrive.

The time to visit is probably now. For Cubans, change is exciting, but if you’re an American tourist who’s privileged enough to be nostalgic about a lifestyle that’s been preserved by deprivation, you should probably already have a plane ticket. In Viñales, a town with one main street that stretches half-dozen blocks, entrepreneurs are already planning to build a 100-room hotel. Change, when it comes, will come quickly.

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Bring all the money you plan to spend in cash. The economy is still cash-based, and you will only make your life difficult if you try to use an ATM or rely on a credit card.

For that matter, bring all the gear you hope to use. Cubans are incredibly resourceful, and have a genius for giving all sorts of odds and ends a second life. But you don’t want to be trying to buy a carabiner or even a pair of hiking boots here. Odds are, you won’t be able to.

Water is essential to life, but on the island, it’s often easier to buy rum. While that sounds delightful in principle, in the middle of a sweaty day of climbing, it’s less pleasant. You can purchase water bottles, but they might not always be in stock. A Steripen or a little bleach goes a long way. (Or, if you’re lucky, you can opt for a fresh juice. Many enterprising farmers have built shade shelters and traded hoes for crushing fresh oranges for thirsty tourists.)

Be willing to be flexible. There are Lonely Planet guides for Cuba, but it’s one of the few places left where they aren’t that helpful. If you’re not too determined to arrive at a set destination, you’ll have more fun. A popular phrase here, resolver, encapsulates the Cuban ethic of making do-if you’re open to doing the same, you’ll find beauty in all sorts of unexpected places.

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Photos: Simon Matzinger, Doug Kaye

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