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Since regulations prohibiting travel to Cuba were relaxed in January, U.S. travelers have been clamoring to visit—though trip planning takes some determination. Senior digital editor Laura Dannen Redman went step by step through the process with Traveler aviation correspondent Barbara Peterson, answering all the questions she—and you—might have.
LR: I want to go to Cuba to cover the Havana Biennial, running May 22–June 22. I’m a journalist, so I fall under one of the 12 categories of U.S. traveler allowed to visit now. My dates are flexible. So…what should I do first?
BP: Will you be traveling as part of a group or as an individual? If it’s the former, dozens of companies specialize in what’s known as “people to people” packages and like most organized tours, you’d be part of a group that is going for a designated purpose—humanitarian, research, or cultural—that meets the legal requirements.
The good part is that they’ll take care of the paperwork—obtain a visa (good for 30 days), get you on a charter flight from the U.S., and book a hotel room, all rolled into the total price. Prices vary, though we found trips that range from three to nine days for under $3,000.
I’d really rather go as an individual. Any problem with that?
No, since you're already authorized to go under the new rules, and you don’t need to be in a group to buy a seat on a chartered plane. But remember, tourism is not a valid reason to visit Cuba and you must be able to document that you are there for the approved purpose. Spend too many hours sunning on the beach or sipping mojitos, and you could run afoul of U.S. enforcers. Under rules spelled out by the Treasury Department’s Office of Foreign Assets Control, you’re supposed to keep all documents related to your trip—a schedule, a record of appointments, receipts, and so on—for up to five years in case you get audited.
What kind of documents do I need for my trip?
Basically, the Cuban government requires that you possess a passport that’s valid for at least six months beyond the dates of travel, proof of health insurance coverage, and a visitor's visa.
Embassy re-openings are still in the works. How do I actually get a visa?
Consider working with a charter operator to get the ball rolling; a few of the bigger companies are Cuba Travel Services, Marazul, and ABC Charters, which asks you to download a travel affidavit affirming you meet the Treasury requirements. But when Traveler's Cynthia Drescher talked to Brian Kelly, founder of ThePointsGuy.com, about his trip to Cuba in early January via the Cayman Islands, Kelly had an easier experience: “Procuring my visa took literally a $20 bill and a smile from a Cayman Airways ticket agent; [Cuban immigration] didn't even ask for the reason for my visit when going through. They saw the tourist visa and asked if I wanted a stamp and I was in.”
Do I need to get a visa before I book my flight?
That depends. If you’re planning to fly via a charter flight from the U.S., you can fill out the visa application form at the time of booking, as well as the affidavit. If you’re taking scheduled airline flights via a third country, such as Mexico, as Kelly says above, you may not need a visa until you’re actually halfway there and checking in for your Cuba-bound flight.
Isn’t flying through a third country kind of dodgy?
Until very recently, it was—an unknown number of U.S. travelers skirted the ban on travel to Cuba by going that route. Now, though, as long as you’re following the rules in every other respect, the question of how you fly there is really up to you, according to a Treasury spokesperson I talked to last week.
Is there any way to do an apples-to-apples comparison of all flights and fares, both charter and scheduled airline, by date? Are they listed in any search engines or booking sites like Expedia or Priceline.com?
Not yet. After the rules changed in January, Kayak.com announced that it would list flights for informational purposes, though you can’t book through the site or see the availability of seats. Cheapair.com also lists some options. As of yesterday, there were dozens of flights via Copa, Cayman Airways, and Aeromexico via a third country, some with extended layovers. You'll likely end up doing your own legwork or go through a travel agency who can help. Brian Kelly worked with tour operator AC Journeys to research charter flights.
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I hear that JetBlue has charter flights—what’s that all about?
JetBlue just announced it will begin flying weekly non-stops on Fridays, starting July 3, from its hub at JFK to Havana, in cooperation with Cuba Travel Services. The planes and crews will be JetBlue’s, but keep in mind that JetBlue can’t sell the tickets because U.S. airlines are still prohibited from operating scheduled flights to Cuba. The seat inventory and sales are all under control of the charter operator. There's a growing number of charter flights leaving each week from the U.S. to Cuba, most of them from south Florida, and prices range from around $400–$500 round-trip from Miami and about $850 from New York. American Airlines flies from Miami and Tampa; Sun Country already has a weekly flight on Tuesdays from JFK. The Transportation Department lists public charter filings on its site.
If I’m a journalist but my husband isn’t, can he still go with me?
A lot of us might want to go with someone, but the Treasury Department takes a dim view of family members tagging along if they don’t qualify under the rules.
What if my husband goes on, say, a humanitarian project?
He would be able to go, but he has to have documentation with him of his (approved) mission like you do. Per my Treasury contact, "An entire group does not qualify for the general license [authorizing travel] merely because some members of the group qualify individually." A spokesperson for Customs and Border Patrol added that "it is the responsibility of all returning residents to declare if their travels have taken them to Cuba. Such travelers must be prepared to present lawful authorization for Cuba-related travel to CBP officers upon request."
Flights are booked. Do I need special permission to book a hotel or Airbnb if I’m not going with a group?
No, though you’ll have an easier time of it if you work with a travel agent or Cuba travel specialist who can open doors. Havana hotels are packed right now—On Cubamagazine reported in April that Old Havana hotels were nearly booked solid. Travelerhas worked with Cuba specialists Adam Vaught at GeoEx and Tom Popper at Insight Cuba. The Points Guy worked with Johnny Considine of Esencia Experiences, who bills himself as a "luxury concierge.” A. Nash Travel in Toronto also books a lot of travel to Cuba. The other advantage of using these guys? You can pay themwith your credit card.
How much U.S. cash should I bring, if any?
In theory, you can now use your American credit card; in practice, very few establishments accept them, according to The Points Guy. Amex and MasterCard say they're working on it, but that won't help if you're going soon. Plan to bring plenty of cash and prepay whatever you can—hotel, rental car, etc. If you have a foreign credit card, that might work; Kelly's traveling companion when he went in January used her Spanish credit card.
What kind of souvenirs can I bring home, if any?
You can bring up to $400 worth of goods, including $100 worth of tobacco and alcohol products (combined).
Can I use Wi-Fi there?
According to reports from recent visitors, Internet is very difficult to access in Cuba, aside from at the larger Havana hotels; expect to disconnect from your devices—and plan accordingly.
Is there a way to get to Cuba I haven't thought of?
If you can wait until later this year, go by cruise ship. Traveler'sPaul Brady reports that "the 48-passengerPanoramawill let travelers explore Cienfuegos, Cuba before embarking on a seven-night sail to Havana. The new offer, from International Expeditions, makes its first departure late this year and is operated as a legal, people-to-people trip open to any American visitor."
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