How to Fly to Cuba From America Right Now

Without routing through another country first.

bySean Evans|
How to Fly to Cuba From America Right Now

Last week, the U.S. Department of Transportation picked the six U.S. airlines that won the rights to operate up to 90 round-trip flights per day to Cuba. American Airlines, Frontier Airlines, JetBlue, Silver Airways, Southwest, and Sun Country Airlines all received the go-ahead to begin flying from hubs like Miami, Fort Lauderdale, Chicago, Minneapolis and Philadelphia starting in the fall. But what if you don’t want to wait until scores of Americans overrun, and subsequently ruin, the forbidden isle? Until recently, the norm was to jump off through Mexico, Canada or the Bahamas. But even though the major airlines haven't yet begun flying to Cuba yet, you can fly directly to the island nation next week—with zero oversight from the U.S. government—thanks to a pair of companies.

The first is a Miami-based charter outfit called Xael Charters, who runs flights to and from Havana, every day except Wednesday. They can typically get you on a private charter on an MD-80 jet two or three days after you inquire. While U.S. and Cuba relations have relaxed, until those aforementioned airlines start up service, you’re supposed to meet one of 12 reasons for visiting. Tourism isn’t among the dozen, but Xael is quite willing to work with you to find a category for you to squeeze into.

For example, “research” is a valid option. To satisfy that wonderfully broad requirement, all you need is a note on company letterhead, with a loose, plausible itinerary tangentially related to your business. It needn’t be specific, a representative assured us. Who checks to see if you’re telling the truth? “Oh, no one,” the rep laughed. “This is self-certifying. We don’t call anyone and no one ever gets denied.”

Sven Creutzmann/Mambo Photography/Getty Images

Cost for the roundtrip jaunt from Miami is $419, plus an $80 fee for the Cuban visa. For additional fees, Xael will book your hotel room, in-country travel, and can arrange tour groups for you.

Your second option is Cuba Travel Services. The Miami to Havana flights depart daily, or you can fly direct from New York City on Tuesdays and Fridays, Tampa on Thursdays on Sundays or Los Angeles on Saturdays. They also advise you of the legitimate reasons for travel, in greater detail, but the woman manning the phones said you don’t have to submit anything to anyone. “You should keep an itinerary of where you went and what you did, in case OFAC audits you,” she said. That alphabet soup stands for Office of Foreign Asset Control, the federal watchdogs for the U.S. Treasury. They have the right to check into your trip up to five years later, the woman explained. How often does that happen? “Before Cuba opened up, a little bit. Now? Never.”

The cost for a three and a half hour direct flight from JFK airport is $849 and you’ll spend an additional $85 for the visa at the airport. There’s also a $25 Cuban departure tax that you pay in advance for at JFK. (Cuba Travel Services will also book you a hotel, with nominal administrative fees of only $10 per person.) That fare is not exactly cheap, but it is direct and there’s a huge added bonus. “We use JetBlue planes,” the woman said, and you get all the typical JetBlue amenities—snacks, TV, et cetera. You can even upgrade to an Even More Space seat for an additional $125. The best part? You can book directly online.

As for what to do when you land in paradiso, check out our Gearhead’s Guide to Cuba.