“There are wonderful places to stay in Havana with five stars, but the demand is high,” said CTN sales agent Javier Arevalo. As he flipped through availability at Havana's most luxurious hotels—the Saratoga, Iberostar, and the Melia—he found slim inventory through the month of October.

Consider a Cruise
Pursuing a project in Cuba has unparalleled logistical challenges. All staff need to be hired through a government-run agency that charges hoteliers roughly $700 a month per employee—but keeps a majority of that sum for itself. Bonuses for employees who deliver good service are strictly forbidden, which means there’s little incentive to provide a five-star hospitality experience. What’s worse, supplies on the island are limited in quality and availability, and business owners are prohibited from importing what they can't buy locally.

There’s one categorical exception to all these rules: cruises.

The leader thus far is Fathom, a volunteerism-oriented cruise line owned by Carnival, with weeklong itineraries that dock in Havana, Cienguegos, and Santiago de Cuba. The cabins on the 704-passenger Adonia are brand new, with floor-to-ceiling windows and balconies and access to numerous hot tubs on the pool deck.

Starting in January 2017, there will be an even more alluring option for luxury-seekers: yacht-based cruises with Ponant. The itineraries are still being finalized, but the company says the seven- and eight-night voyages will stop in Havana and Santiago and sail on the 64-guest flagship, Le Ponant. The cabins are small but sleek, with nautical-inspired décor and satellite phones (which are especially handy in disconnected Cuba).

Check Airbnb
Hotels around the world are afraid of Airbnb’s competition, but in Cuba, home sharing came first.

“Cubans have been opening their doors to all types of travelers from all over the world for more than 20 years through the country’s existing cases particulares (private homestays) network,” said an Airbnb spokesperson, who claimed that the company is learning more from Cuban hosts than the hosts are learning from Airbnb’s hospitality experts.

Rooms in private homes—beautiful ones—can cost as little as $44 and offer an opportunity to connect with locals in meaningful ways. And thanks to a transparent booking system and satisfaction guarantees, many of the question marks associated with hotels simply don’t apply. It’s one of the best options for discerning travelers, both in Havana and beyond.

Wait Out the Rush
If you can resist the temptation to book the first commercial flights out of the U.S.—they depart on Aug. 31—you might find it worthwhile.

For one thing, overcrowding has become an issue. Even before Obama approved independent trips this March, the country had already seen a record-breaking million travelers in the first quarter of the year. One report by the New York Times discovered that some travelers were sleeping in taxi drivers’ back seats for lack of better options. So waiting for Cuba to put finishing touches on some of its 50,000 planned hotel rooms may not be a bad idea.