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How to Travel to Cuba Now

by Jeralyn Gerba
Street scene in Habana Vieja. Photo by Jeralyn Gerba.

CUBA – Cuba. It's rough around the edges, nostalgic, romantic, and on every traveler's lips these days. The latest round of incremental restrictions (on financing exports, shipping products) were lifted by the United States government on January 27, 2016, but the two countries have a long way to go until relations are as "normal" as they are with other countries. What that means for the conscious traveler? Due diligence and planning ahead.

Smoothing Out the Wrinkles: Cuba and the United States

According to the U.S.-Cuba Trade and Economic Council, there are a number of things the Cuban government has done or has agreed to do since President Obama's announcment about the ease of restrictions to the island nation in 2014. The ones that relate specifically to travelers include restoring diplomatic relations, reopening embassies in Washington and Havana, authorizing roaming agreements with Verizon and Sprint, expanding exports, and opening lodging operations to Airbnb. A pretty big deal!

The Long View and a Word of Caution

While Cuba has raised its flag on U.S. soil and diplomats mingled at the State Department for the first time in decades, huge challenges remain. The United States still has a trade embargo against Cuba and a controversial military presence at Guantanamo Bay. To be clear: It's not all jaunty fedoras and icy mojitos on the other side. Cuba is an authoritarian state. Perceived threats to authority or general dissent are routinely met with repressive responses: surveillance, detention, interrogation — of both Cuban citizens and foreign visitors. Human rights conditions aren't good either: The government limits freedom of expression and peaceful assembly. Longstanding policies (and grudges) will have to come to an end before full relations can be restored.

It is undeniable that travel to Cuba is on the rise. No doubt you've heard plenty of people talk about visiting "before it's too late" — before the well-worn patina is replaced with shiny new emblems of the flood of capital and global connectivity.

Engagement, Not Estrangement

Here's how to get five steps closer to Cuba:

Contrary to the media hype, tourist travel in the typical sense is still not allowed. All trips must be "purposeful" and must fall under one of twelve types of general travel licenses (i.e. religious, academic, arts-based). This used to be a really lengthy and daunting process that took months. Now, under the new regulations, travelers can self-certify, marking a box on their application to denote the purpose of the trip and creating a schedule of activities related to their category of travel. Give yourself 8-12 weeks to secure all your details (lodging, itinerary, paperwork) for a great trip. See our Cheat Sheet for more details and explanation.

Once you have received the green light for a general license, make sure your passport is up to date and you obtain a visa from the Cuban Embassy in Washington D.C. or consular offices in New York City. As of this writing, the Cuban embassy website had a lot of dead ends and broken links. (Your best bet is calling and talking to a human.) The path of least resistance is working with a travel agent or third party who can take care of the paperwork for you.

JetBlue, United, and American will fly direct ... eventually. Until then, you'll have to take a charter from a main airport hub like NYC or Miami. Tickets are pricey, and there's a weight limit on luggage, but it's pretty straightforward and easy, though there are extra costs you can't get around. Like having to buy non-U.S. medical insurance before entering Cuba. You can obtain a temporary policy at immigration at the airport.

Hotels are government-run, often expensive, and a little run-down. The fact that Airbnb is up and running is a major game-changer, as being able to book casa particulares (private homes) puts the power directly into the hands of Cuban individuals. If you have something very specific in mind (like a private swimming pool or a hotel suite), a travel agent or a third-party fixer can be a great asset here.

Enroll in STEP in case of an emergency (the embassy will be able to send you alerts and warnings; family will be able to get in touch), and check out the State Department's Consular Affairs for pertinent info you may need while traveling.

Travelers can bring back $400 worth of goods to the U.S., including up to $100 in alcohol and tobacco products. ATMs and credit cards for Americans are in the works, but who knows how long it'll be until American banks can offer reliable services. As it turns out, cash is universal.

Cuba is an incredible place, and the gray areas only add to the adventure. As I was told before I visited a few years ago, "Have a fun and slightly surreptitious time."


Government Sites
Cuban Embassy in Washington D.C.
Bureau of Consular Affairs at the U.S. State Department
U.S.-Cuba Trade and Economic Counsel, Smart Traveler Enrollment Program (STEP)

Tour Operators and Fixers
Esencia Experiences (the excellent Spain-based agency helped Fathom get to Cuba)
Cuba Travel Network
Cuba Travel Services
Smithsonian Journeys
Times Journeys


Fathom Guide to Cuba

We make every effort to ensure the information in our articles is accurate at the time of publication. But the world moves fast, and even we double-check important details before hitting the road.