Luxury Travel

The Secrets to Booking a Luxury Trip to Cuba

Hint: It’s all about managing expectations.

How to Plan a Vacation in Cuba

The Hotel Inglaterra has been one of the best places to stay in Havana since it opened in 1875. Its colonial façade and bright neon signage fit right in with the nearby capitol building and Gran Teatro, and its guest book includes such famous names as Cuban national hero José Martí.

There’s just one catch: The property is stuck in time, just like the rest of Cuba. You’ll have to pay $312 a night for what looks like a Holiday Inn, albeit one with pretty terracotta-tiled floors.  

In the six months since independent travel from the U.S. was officially whitelisted, tour operators have introduced itineraries and major airlines (such as American and Jet Blue) have scheduled their first flights into Havana. By the end of the year, the Inglaterra will be rechristened as part of Starwood’s Luxury Collection, becoming the company’s second hotel after a Four Points by Sheraton opened earlier this year. 

Street scenes from Havana
Street scenes from Havana
Source: cazenove + loyd

But when it comes to hotels in Cuba, there’s almost always a catch, just as there is at the Inglaterra—and that problem isn't likely to go away soon.

Just ask Leo Ghitis, owner of one of Costa Rica’s most luxurious hotels, Nayara Springs. When he was approached to open a property in Havana, he took the first flight out. “I received a tremendously warm welcome,” he said about his meetings with the minister of tourism and top government officials. “But even after getting the red carpet treatment, I had to decide to postpone my plans,” he said, citing major infrastructural limitations.

That doesn't necessarily mean you have to settle for mediocre accommodations should you choose to visit. Despite the island's many challenges, comfortable and beautiful options do exist if you know where to look. And if you play your cards just right, a five-star trip to Cuba can be well within reach.

 

Don’t Go It Alone

The rooftop pool—a rare amenity—at the Hotel Saratoga
The rooftop pool—a rare amenity—at the Hotel Saratoga
Source: Hotel Saratoga

Just because you can buy a plane ticket and fly to Havana with your significant other doesn’t mean it’s the best place for a spontaneous getaway.

“Many of the larger reputable hotels in Havana are reserving their rooms only for big group trips of 40 to 60 travelers,” said Melissa Biggs Bradley, founder and chief executive officer of Indagare, a members-only travel company that has been coordinating trips to Cuba since 2011. The reason, she says, is that they “prefer to sell a few big blocks of rooms instead of one-off reservations,” which results in little availability for independent travels.

There are other benefits to going with a group, aside from having an organizer who can help you navigate all the required paperwork. Bradley advises DIY travelers that bookings made on many hotel websites can get bumped or cancelled by the tourism authority—often without warning. Plus, she says photos can be misleading; a perfectly nice-looking hotel may be subject to frequent water shut-offs or power outages. (Those who aren’t members of Bradley’s organization can book luxury trips via Ker & Downey and Cazenove + Loyd.)

A suite at the Hotel Saratoga
A suite at the Hotel Saratoga
Source: Hotel Saratoga

If you’re dead set on going without a group, book through Cuba Travel Network, which guarantees all its reservations by selling rooms from preassigned blocks. But plan on booking at least three months ahead.

“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

Ponant's flagship yacht, which will begin sailing to Cuba in January 2017
Ponant's flagship yacht, which will begin sailing to Cuba in January 2017
Photographer: Guillaume Plisson/PONANT

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.

A stateroom on Le Ponant
A stateroom on Le Ponant
Source: PONANT

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

The Havana Sea, one of many beautiful options on Airbnb
The Havana Sea, one of many beautiful options on Airbnb
Source: 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.

Rose de Ortega, another standard-setting Airbnb listing in Havana
Rose de Ortega, another standard-setting Airbnb listing in Havana
Source: AirBnB

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

Vintage cars in Havana
Vintage cars in Havana
Source: cazenove + loyd

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.

Infrastructure will also get better with time. A key example: Wi-Fi availability.

Ghitis, the hopeful hotelier, described deep frustration at the quality of Wi-Fi on each of his recent visits: “It can take several hours, literally, to be able to see your e-mail,” he said. “If you remember when AOL started with dial-up, that’s what it’s like. And you get disconnected every one or two minutes.”

That’s if you’re lucky, he claimed—most hotels don’t have Wi-Fi at all. This problem is being phased out: Last month, the country began installing its first public Wi-Fi hotspots across the island.

Street scenes in Havana
Street scenes in Havana
Photographer: Eliana Aponte/Bloomberg

None of this means that Cuba’s stuck-in-time character is in danger of disappearing overnight.

“Cuba’s not going to change tomorrow—or in two years,” said Cuba Travel Network's Arevalo, a lifelong local. But he’s optimistic about what his country has to offer. “People are already going to Cuba, loving it, and wanting to go back again and again. We’re busy every day, and we’re thankful for that.”

Havana by night
Havana by night
Source: cazenove + loyd
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