Rules About American Travel to Cuba Have Changed Yet Again

havana cuba
Photo by Karel Miragaya
Cuba has become like that significant other you can never quite seem to break up with. They push you away, only to pull you back. Then you push away, but they reel you back in again.

For decades, U,S. citizens couldn’t go to the island nation. Then, in 2015, President Obama relaxed restrictions on American travel to Cuba so some of us could.

Now, some of us still can, but not as many as before. The bottom line is that President Trump would like to make it very difficult for you to get to Cuba. The Washington Post reports he’s looking “to steer economic activities away from the Cuban military, intelligence and security services … and encourage the government to move toward greater economic freedom.”

But, what does this mean in practical terms? Let’s unpack it for American travelers.

First, while “tourism” to Cuba is technically restricted by the embargo, Americans can still legally visit. There’s an entire niche within the travel industry — including cruise lines, commercial flights, big-name hotel brands, Airbnb, and dozens of tour providers — with an active, vested interest in accepting and working with American travelers to facilitate their visits to the island. However, under the new regulations, planning a visit to Cuba now requires a few additional hurdles.

The caveats are more like speed bumps than insurmountable roadblocks of red tape. In broad terms, individual visits to Cuba will, for the most part, no longer be allowed. Visitors must be able to prove to the U.S. government’s satisfaction that their itinerary includes meaningful daily interaction with locals in an effort to directly bolster the Cuban economy through private enterprise (and not the Cuban military). The U.S. government’s interest here is that American travelers are not patronizing businesses owned by the Cuban military. Unfortunately, the list of banned businesses — including many restaurants and hotels throughout the country — is extensive and not always clear. The only easy way to satisfy this is to plan your trip with a group tour as they ensure that your entire itinerary is above board.

If group travel tours aren’t your thing, it’s still possible to book an individual trip to Cuba. You must first fall under one of the 12 authorized categories of travel to Cuba. For the everyman, the only viable categories are as a journalist (for, say, bloggers), or for educational or religious activities (both of which are vaguely defined). However, individual travel to Cuba under even these three categories can be tricky. On your return to the U.S., you’ll need to prove to Customs and Border Patrol that you had daily, meaningful interactions with Cuban locals. What this means in practical terms is almost impossible to define. Individual travelers will be much more heavily scrutinized in this regard. To dodge any potential conflict by unknowingly staying at a government-owned hotel, travelers are best served by crashing at casa particulares. Most of these are basic Airbnb rentals that involve renting a room or an entire apartment directly from a Cuban citizen.

It’s worth noting that anyone with existing travel plans to Cuba will not need to cancel their trip. Although the new regulations went into effect in November, administration officials have confirmed that the revised ban will not impact anyone who’s already booked a flight, cruise, or tour.

Feature image by Karel Miragaya.

Travel

10 Reasons to Visit Norway in 2019

The picturesque ruggedness of Norway is just part of the appeal of what may arguably be one of the most beautiful countries on the planet.
Travel

21 Best Travel Books to Inspire Your Next Adventure

Get out of town ... or just go to the library. Travel books simulate the sensations of sailing, sightseeing, and setting out to explore.
Auto

All the Presidents’ (Coolest) Cars: A Look at How the POTUS Rolls

The presidential state car serves as a reflection of technological progress, the style of the time, and the stark realities of safety and security concerns.
Travel

Win a Private Island Getaway for You and 7 of Your Closest Friends

Bring the entire squad on an ultra-luxe Belizean getaway worthy of a one-percenter.
Food & Drink

Heading to Hawaii? Make Your Reservations at Manta Restaurant to Eat Big Island Beef

How can cattle raised in Hawaii stand-up to beef carefully coddled for years in Japan, Australia, and the mainland U.S.? Pretty damn easily, that's how.
Living

Detroit’s Shinola Hotel Has Us Feeling Right At Home

With stylish guest suites and a social “living room,” the Shinola Hotel honors the Motor City’s past while looking to a bright future.
Living

The Jamaican Villa Where Ian Fleming Created James Bond is for Rent and It Is Amazing

You can vacation at the birthplace of secret agent 007, complete with butlers to make your martinis.
Travel

The Best Travel and Adventure Documentaries on Netflix Right Now

If you're reading this, you're staring at a screen. Wouldn't you rather be exploring a different part of the world than the Internet?
Outdoors

4 of the Most Dangerous Hikes in the World

You'll need a healthy dose of fear and a desire to push your self to the edge — just not over it.
Travel

‘App in the Air’ Could Help Travelers Survive the Next Government Shutdown

It's like an airport survival kit in your pocket. It will be handy long after the government shutdown ends (again).
Travel

The Palms Casino’s Newest High-Roller Suites Have a Bowling Alley and Whiskey Room

The Hardwood Suite is a basketball-centric masterpiece, while the Kingpin suite is a bowling bro's paradise.
Travel

Celebrate Your Single-ness This Valentine’s Day with a Cheap Vacation

Contiki is looking to make solo celebrations even better with deeply discounted travel packages for Singles Awareness Day.
Auto

PlugVan Converts Most Vans Into Full-Fledged Campers in 5 Minutes

Your van can be backcountry-ready for the weekend and back to work Monday morning.
Travel

Enjoy a Different Kind of Island Life at this Private Scottish Escape

Eilean Shona is a self-described, lakefront “Neverland” where visitors are encouraged to appreciate the lost art of sitting still and doing nothing.