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How to travel to Cuba (Yes, you can!)

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A couple dances in Cuba.

“I’d love to go to Cuba — but the sanctions are back on, so I guess I can’t,” a friend of mine opined recently after perusing my Instagram pics of the trip to the famed Caribbean island over New Year’s.

This is not an uncommon sentiment.

Ever since President Trump reinstituted trade, commercial and economic embargoes against Cuba in 2018, American travel to the country has dropped precipitously — but you can still go. In fact, airlines like Jet Blue, Delta, Southwest and American Airlines have direct flights from cities like New York City, Boston and Miami to Havana on a regular basis.

But it can be tricky.

Enlarge ImagePeople hang out near the ocean in Havana.
People hang out near the ocean in Havana.Annie Wermiel

“We are getting questions every day from confused travelers wanting to understand and adhere to the travel rules,” CubaCandela founder and CEO, Chad Olin said.

Olin — whose company runs luxury tours to Cuba — registers his guests under the “Support for the Cuban People” travel category, and has created a guide to traveling in the country.

As the guide notes, “’Support for the Cuban People’ is authorized by general license. This means you do not need to request permission from the US government or obtain any physical document from the US government at any time. A general license is based on the honor system, however, the US government reserves the right to audit your travel, meaning they can request that you provide your legal itinerary and receipts.”

This means that when you go to Cuba — you’re not lounging around all day, you will have to have a full-time schedule of “supportive” events.

That means you should “buy services from Cuban entrepreneurs, such as home rentals (Airbnb), meals (private restaurants called paladares), transportation services (taxis) and cultural activities (Airbnb experiences); Participate in enriching cultural activities of your choosing from 9 a.m. – 6 p.m. daily. … Avoid sitting on the beach all day — you must engage with the local people of Cuba.”

Enlarge ImagePeople walk down a street in Havana.
People walk down a street in Havana.Annie Wermiel

But it doesn’t have to be exhausting. Olin’s guide notes, “For self-guided travelers, we recommend that you book a rental home on Airbnb because that automatically qualifies as supporting a Cuban entrepreneur (the homeowner). Then, we recommend that you eat two meals per day (lunch and dinner) in privately owned restaurants called paladares. When traveling around Cuba, use taxis operated by Cuban entrepreneurs.”

Visitors also have to “engage in meaningful interactions with the Cuban people” as well as keep a copy of their schedule and receipts for five years … just in case.

Many people opt for a company like Cuba Candela because, due to the sanctions, Americans are not allowed to spend money at Cuban government-owned businesses listed on the Restricted Entity List (which means much of Old Havana) — and you can’t use an ATM or credit cards in the country. So, if you go on your own, come armed with a boatload of cash — if you run out, there’s nothing you can do.

Also remember that, because US citizens are not allowed to be “tourists,” there won’t be a lot of free time.

“If getting to know the local people is not your typical style of travel, or if you simply want to lay on the beach for a week, consider another destination,” Olin said.

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