The Travel Detective

How U.S. Citizens Can Travel to Cuba

Locations in this article:  Havana, Cuba

In 2014, Barack Obama announced that he and Cuban President Raul Castro had begun the process of normalizing relations between the two countries. Part of that agreement included lifting some of the travel restrictions for United States citizens, which would allow them to travel between Cuba and the U.S. for the first time since 1963. However, for many Americans, there are still more questions than answers.

So who can actually go to Cuba? Just about any American can go—if they go on a cruise ship and follow the Treasury and Commerce Department regulations. What are those? A traveler has to sign an affidavit saying that he or she is going under one of twelve approved, sanctioned ways—people to people, education, research, journalism, etc. Most people pick people to people.

But in June of 2017, President Donald Trump announced that he would be tightening travel restrictions, eliminating individual people-to-people and educational trips. These visits had been previously defined by travelers having “meaningful conversations” with Cubans—or visits to places where they could learn about Cuban life and culture, while exploring Cuban cities on their own. The Trump administration will require travelers to book a trip with an official tour operator—and those will include cruise ships and commercial airlines that comply with the new policies.

Of course, if you fly to Cuba on carriers like American, Delta, JetBlue, or Southwest, you’ll need a hotel room. The influx of American travelers to Cuba has left rooms in short supply, because the Cuban infrastructure has just not caught up with the additional demand for accommodations.

But cruise ships don’t need a hotel. They’re their own floating hotels. As a result, from two to seven thousand people a day are roaming the streets of Havana—coming ashore in ports that can barely accommodate even one ship.

On one trip, I sailed on the Carnival Paradise from the port of Tampa. Then, about 18 hours after leaving Florida, the ship arrived in the iconic Harbor of Havana, sailing right past El Morro.

The new regulations will likely have little impact on ships like the Paradise because passengers sign up for structured shore excursions before disembarking the ship. They can choose to experience the sights and sounds of Havana, or explore the country’s colonial past—or even visit the famed Tropicana night club, which was a favorite watering hole of Ernest Hemingway, Marlon Brando, and even John F. Kennedy.

There are lots of cruise lines sailing here, like Regent Seven Seas, Norwegian, Royal Caribbean, Azamara, Lindblad, and even luxury yacht line Groupist.

With so many cruise lines visiting the island, there are itineraries lasting just a few days—and others that are more than a week long—and they’re at every price point. You can go to ports such as Cienfuegos, Santiago de Cuba, and Trinidad.

But of course, the most popular remains Havana. It’s a city that famously still feels as though it’s trapped in the 1950s and conjures up notions of romance, adventure, art, music, tropical daiquiris—and of course, Ernest Hemingway—who lived and wrote here for nearly two decades.

As a matter of fact, one of Hemingway’s favorite hangouts was El Floridita, which also claims to be the home of the daiquiri. To avoid any confusion, there’s a handwritten plaque on the wall making it clear where he preferred his drinks.

I’ve been coming to Havana since 1978—nearly 40 years. That makes me one of the lucky ones. I’ve seen all the changes—and I’ve seen the things that haven’t changed. One of the things I do every time I come here is visit a place that’s been here since the 1930s—the Hotel Nationale, once owned and operated by mobster Meyer Lansky.

Why? For a very important family reason. Back in 1947, my parents actually honeymooned here, and a couple of years ago, I found their room number. I got the hotel to open the door, went into the room, and guess what? Other than the legacy touch tone phone and the color TV set, nothing had changed. It’s part of the beauty that still remains in Havana.

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By the Peter Greenberg Worldwide team for