Explore Cuba: Travel + Leisure’s Top Destination of 2025

Travel to Cuba: Milestones in Tourism

When iBestTravel sent writer Gary Shteyngart and photographer Frederic Lagrange to Cuba in January 2015, there was little way of knowing just how rapidly, or dramatically, things would change for the country. Shteyngart reported “flying into one Cuba and out of another.” He had arrived just as the Obama administration made major moves to re-establish diplomatic relations.

By the time Shteyngart’s approved “people-to-people” tour dispersed, Americans could (more or less) visit the country on something of an “honor system.” Lagrange’s pictures capture a similar story: a place preserved in amber, on the verge of a huge cultural shift.

iBestTravel is always seeking out the next, great places to travel, and it just so happens that the most intoxicating destination in 2015 lies just 90 miles south of Key West, Florida. It’s really no surprise that Cuba has earned the title of Destination of the Year. After all, it’s been forbidden fruit for American travelers for more than half a century—Cuba is the only country the U.S. has ever banned its citizens from visiting. It wasn’t until this time last year that the Obama administration significantly eased travel restrictions.

Exploring Cuba: A Traveler’s Paradise

Spurred by traveler enthusiasm for an accessible Cuba, airlines and cruise companies have scrambled to offer a way in. It happened quickly; the allure of the island’s time-capsule qualities—like antique Ford Fairlanes and Buick LeSabre convertibles growling down cobblestone streets—may fade fast, even if the Che Guevara portraits on Havana’s Art Deco and colonial façades remain.

Key Milestones in Cuba’s Tourism Development

December 17, 2014: Obama’s Plan

The Obama administration announced plans to restore diplomatic relationships between the U.S. and Cuba. In doing so, President Obama made travel ever easier.

January 16, 2015: Rules Ease Up

Straight, lounge-on-the-beach tourism is still prohibited, but new rules made it possible for Americans to travel to Cuba without applying for a license, so long as the trip remained within 12 pre-approved, and rather vague, categories. Best of all? Americans can now bring back up to $400 in souvenirs, and $100 of that can be rum and tobacco.

March 1, 2015: Credit Cards Accepted

MasterCard unblocked usage to Cuba, allowing American credit card holders to use plastic on their travels.

March 4, 2015: Conan Arrives

Conan O’Brien aired a one-hour special, Conan from Cuba. The comedian, donning a white linen suit, got drunk at the Havana Club Rum Museum, attempted to dance the rumba, and learned to roll a Cuban cigar.

April 2, 2015: AirBnb Arrives

Over 1,000 Airbnb listings in Cuba appeared on the home rental site—and the number has easily doubled since. With a major lack of hotel infrastructure, the country’s existing network of casas particulares (guesthouses) is crucial for accommodating the influx of travelers.

April 15, 2015: Online Booking

CheapAir.com became the first booking site to sell tickets for flights to Cuba.

May 6, 2015: Ferries

Four passenger ferries got the “thumbs up” from the U.S. to begin trips between Florida and Havana.

May 29, 2015: Open for Business

Cuba may still be under a U.S. economic embargo, but it dropped off the State Sponsors of Terrorism list this summer. Now, private companies and banks can do authorized business with the country.

July 3, 2015: JetBlue in Havana

JetBlue made its first flight from New York City to Havana, becoming the first major U.S. carrier to make the trip.

August 14, 2015: Embassy Opens

John Kerry helped celebrate the reopening of the U.S. embassy in Havana, marking a significant diplomatic milestone.

September 17, 2015: Verizon Dials In

Verizon announced that it would become the first U.S. wireless company to support roaming in Cuba, allowing travelers to text, make calls, and use data.

September 21, 2015: The Pope Visits

On his way to the U.S., Pope Francis made a pit stop at the Cuban cities of Havana, Holguín, and Santiago—highlighting the significance of renewed relations.

December 12, 2015: LAX to HAV

American Airlines began operating nonstop flights between Los Angeles International Airport and José Martí International Airport in Havana—the only domestic carrier to offer nonstop service between the West Coast and Cuba.

December 16, 2015: Commercial Air Travel Resumes

For the first time in over 50 years, the U.S. and Cuba agreed to resume regular commercial air travel, making it easier and more affordable for both U.S. and Cuban citizens to fly between the two nations.

The Culinary Scene in Cuba

Cuba may not have any Michelin stars yet, but its culinary scene is blooming, thanks in part to privately owned paladares serving everything from ropa vieja to lechita—a seafood dish in a broth of coconut milk, tomato, garlic, and spices—attracting interest from master chefs.

Planning Your Trip to Cuba

American tourism increased significantly this year, and the demand for accommodations is soaring. A number of new hotels are in the works, including options that will provide modern amenities such as Wi-Fi.

Conclusion

There’s no better time than now to visit Cuba—while the country still maintains the rough, faded quality of a vintage photograph. Cuba’s must-see cities are likely to change rapidly, including Trinidad and coastal Baracoa. Already, luxury resorts and multimedia art spaces are springing up across the country.

Whether you choose to arrange your own travel plans or opt for an organized vacation, this captivating destination promises to enchant, entertain, and surprise—even the most seasoned travelers.


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