Travel to Cuba, Demystified

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Written By DanielHaldeman

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There’s no doubt: Cuba has us hooked. Since the beginning of the New Year, any US traveler with a passport has been seduced by this mysterious and “forbidden” destination. But beyond visions of pristine beaches and unlimited boxes of cigars, let’s be real…how does this actually work? A quick internet search about travel to Cuba leaves US citizens confused as to how they can actually get there and what they can do, legally. One thing is very clear: you cannot go to Cuba and just sit on a beach. Period. But all is not lost! Finding the right expert can ensure you make the absolute most out of your experience in Cuba all while remaining above board. We chatted with a few travel professionals who helped shed light on how you can maximize your sultry Cuban vacay.

“Technically Americans still cannot go to Cuba as tourists,” says David Lee, a travel advisor and Cuba specialist with SmartFlyer. “That being said, we are able to ‘customize’ itineraries to create a private trip that is tailored to the specific interests of our clients while still meeting the OFAC requirements for legal travel.”

Before You Go

First, the rules. There are still regulations for US travel to Cuba. Your trip purpose must fall into one of 12 approved categories for travel, which can be found here. Some of the categories most pertinent to US travelers are religious activities, educational tourism, athletic training and the People-to-People category, which is the most popular category. This deals with meaningful exchanges between US citizens and Cubans, and is what most of the group tour companies offer when advertising trips to Cuba.

Do I Have to Go on an Educational Tour?

Technically, yes. “American travelers to Cuba need to be on some kind of tour, which can consist of as few as two people,” says Diane Mullahy, a Cuba specialist with Travel Leaders. “But a program can be customized geared to their desires, whether they are foodies, history buffs, art lovers, photographers, etc.”

Will my vacation be on a coach bus with 25 other people?

The fear with People-to-People exchanges is that the itineraries will be rigid, the groups will be massive and that the experience will be robbed of authenticity. But if you’re smart about the way you plan, you can make your trip to Cuba as intimate as possible all while playing by the rules. A group can be as small as you want it to be, but prices will go up considerably. “It’s not the flight that matters or necessarily the lodging,” adds Lee. “But you will need a full-time guide and driver. It is totally feasible for two people to go to Cuba, it just depends on your budget. One of the benefits is a more flexible itinerary catered to what interests you most. We can make changes on the fly. Travelers won’t feel like they are on a big bus tour with a rigid itinerary and all of these heavy restrictions. The biggest benefit is special access. There are places, sights and tours that the large groups simply cannot enjoy due to the size of the group.””

“We can book private jets, private tour guides and suites at hotels. VIP seating on Havana Air from Miami is also an option,” says Mullahy. “It is just required that there is at least one cultural exchange each day.”

Can I fly there from the US?

Yes. It is now possible to fly to Cuba from the United States. That said, these are still charter flights that cannot just be booked online like a regular vacation. “You have to book these through a travel service provider or through someone who sells Cuba,” says Lee. “Also, these flights are not leaving dailyfrom all locations yet,except Miami which has multiple daily flights. That is changing fast as more routes are added from more US cities.” In addition to flights from Miami, JFK has opened up charter flights and Atlanta and Chicago are looking to come onboard, as well.

What’s Hot?

Cuba is a country frozen in time and is rich with culture, history and art. Yes, there are beautiful beaches, but that’s not why you should be visiting Cuba. “The beach isn’t why Americans should be going there and going as soon as they can,” says Lee. “Eventually a visit to the Cuban beaches will be like going to the Dominican Republic or the Bahamas. But it’s Havana you have to see.”

Havana must be the first stop of any traveler. The city pulses with vibrant colors, historic architecture, the famous classic cars and a nightlife that often doesn’t heat up until 1 am. Be sure to visit Casa Fuster, the residence of artist Jose Fuster, which is a mosaic kaleidoscope of colorful tiles and wacky architecture. Also not to miss are Ernest Hemingway’s home, as well as Havana’s famous cigar and rum factories, and flea markets. One of the most unique highlights of Cuba are the paladares, which are private restaurants that range from storefronts in the center of town to literally one- or two-table establishments tucked into someone’s home kitchen. With private groups it is much easier to visit these smaller paladares. In fact, Lee suggests skipping government-run restaurants altogether and finding the best food in the paladares.

“One of my favorite things to do with clients is explore the off the beaten path locations frequented by an ever growing new class of Cubans entrepreneurs, musicians and artists, you won’t find many tourists in these locations, which range from highly stylized lounges hidden in old mansions to massive bars/art galleries, indy film and performance art venues built inside a renovated old factory,” he adds.

So…can I just go sit on a beach?

Sort of. Cuba has stunning beaches, and some wonderful all-inclusive hotels that sit directly on them. You are going to want to go. It’s all about how you handle it. An American cannot check into an all-inclusive, lather on the tanning oil and bake in that beautiful Caribbean sun. “That being said, if I have a group that wants to see the highlights of Havana and then wants a few days at the beach, we can do that,” says Lee. “We might have on our itinerary an information session with someone from the fishing industry, or a marine biologist. There has to be something cultural about it, but you can have your beach vacation.”

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