Traveling to Cuba as an American is easier than you think—if you read this guide first

The vintage look.
The vintage look.
Image: Reuters/Stringer
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Raul and Barack held an awkward press conference, Travel & Leisure named it “destination of the year,” and all of a sudden, everyone’s talking about visiting a mysterious communist time capsule that’s long been considered off-limits.

I’m talking, of course, about Cuba.

America’s collective wanderlust for a small island 90 miles south of Miami has recently become so great, in fact, that Cuba is reportedly running low on beer. Yet even as the relationship between Havana and Washington DC sputters back into motion, reliable travel information remains difficult to come by. I discovered this the hard way after recently traveling to the island myself. Extracting useful nuggets from the vortex of meandering travel blogs, cranky message boards, and dense government documents was a frustrating and ultimately unhelpful scavenger hunt.

As a result, I planned almost nothing before I got on the plane. Luckily for me, US citizens currently enjoy a comparably simple process. It’s a vibrant, fascinating country brimming with some of the most generously spirited humans I’ve encountered. Every curious and compassionate traveler should have access to the experience. Still, there are a few important things I wish I’d known in advance. (Note: many of these tips assume the reader and/or their travel buddies have some proficiency in Spanish.)

Get your tourist visa at the airport.

It takes about three minutes. As of 2015, Americans are allowed to visit Cuba if the reason for their trip falls into one of 12 categories. These categories are designed to be ambiguous and all-encompassing. They include things like “support for the Cuban people” and “public performances.” You’ll sign an affidavit at the airport declaring why you’re going, and if you have a connecting flight in another country, you can buy your visa there for around $25. If you opt for one of the few direct charter flights from the US, most of the airlines will process the visa for you.

Bring double the amount of cash you think you need.

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Image: Ryan Welsh

Then double that amount. Though some reports say otherwise, American credit or debit cards simply don’t work in much of Cuba. Some people recommend bringing euros, British pounds, or Canadian dollars rather than US dollars because they aren’t subject to the same transaction fee. Personally, I had good luck exchanging US dollars with my taxi driver’s daughter. It all depends on your Spanish language skills, comfort level asking locals for advice, and ability to identify swindlers).

If your confidence level is low, change a small amount at the airport and then look for one of the official cash exchanges, called Casas de Cambio, S.A. (CADECA), which can be found in every major town. The LA Times has a good primer on the two Cuban currencies and the merits of bringing euros vs. dollars.

Pack granola bars.

And a first aid kit. And extra toothpaste. And hot sauce. And anything else you could possibly fathom needing in a pinch. The effect of the embargo is strikingly palpable. Convenience stores are rarely stocked, it’s difficult to find places to purchase food during long treks from city to city, and shops that sell even basic household goods are difficult to find. Pack light, but pack mindfully. A friend who recently returned from a similar trip also recommended bringing personal items—t-shirts, baseball caps, pens—you won’t regret gifting to amicable locals you encounter along the way. “I lost quite a few items in the name of diplomacy and was quite happy I did,” he told me.

Only book one night at a hotel in advance.

It’s good to have a destination in Havana to tell your taxi driver upon arrival at the airport. But beyond that, it’s much more interesting (and inexpensive) to make plans on the fly. Once you’re situated, opt for staying at a family-owned casa particular rather than a hotel. The accommodations are usually clean and lovely, breakfast is often included, and it’s a wonderful opportunity to connect with Cubans. Don’t try to book them before you leave the US, though: While many casa particulares do list their spaces on websites like Airbnb, Cuba’s unreliable internet makes it almost impossible to secure a place online. Instead, look for the signature casa particular sign and check out the available rooms in person.

Make your own itinerary.

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Image: Carly Schwartz

Many reputable travel publications still recommend booking pre-arranged tours through third-party agencies. But if your travel habits are anything like mine—I describe myself as “a spontaneous backpacker who still likes to have nice things”—it’s not worth the cost or constraints. You’ll want to get lost in Cuba’s languid and friendly labyrinth, chatting with new friends, sipping rum on the Malecón, and dancing with street jazz musicians. And if you do choose to embark on an adventure to a seaside colonial town, do it on your own terms.

Once you arrive, it’s not too hard to find your way around, with a little patience. Moreover, violent crime rates in Cuba are incredibly low, so it’s generally safe to wander. That said, don’t seek help from the street hustlers, known locally as jineteros, who approach you with a big smile and an offer to help find a good place to stay or eat. They’re everywhere, and are pretty much guaranteed to be selling a lower-quality experience for a higher price.

Ride in cars with strangers.

Rather than relying on the sluggish government-sponsored bus company to cart you from city to city, take colectivos, the iconic 1950s cars that now operate as underground taxi companies. Colectivo drivers will often crowd outside bus terminals offering cheaper rates, and sometimes you can bargain the price down even further. Casa particular hosts can help, too. And don’t be afraid to share with other travelers, even ones you’ve never met before. One of my most magical Cuba memories was cramming into the back seat of a clunky Ford, windows rolled all the way down, and zooming down the highway discussing international politics with newlyweds from Barcelona and Latvia.

Unplug, abandon your expectations, and embrace the confusion.

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Image: Carly Schwartz

Cuba is a country full of contradictions. The country’s healthcare system is widely considered a model for the rest of the world, but doctors make as little as $35 a month. Crime is virtually nonexistent, but government dissenters are regularly rounded up and arrested. There’s a burgeoning countercultural scene, but most of the public art is pro-Castro propaganda. And it’s true what they say about internet being scarce: if you purchase a Wi-Fi card from a street vendor, you may be able to get spotty service at some public parks and hotel lobbies, but it’s hardly worth the hassle. It’s best to let go of your preconceived plans and expectations and just go with the flow.

Bonus tip: Buy your cigars at the airport duty-free shop.

If a nice guy approaches you on a street corner in Havana and tells you he can get you a box of cigars wholesale from his friend who works in a factory, chances are he’s lying. Even if he tells you he’s studying engineering at the university. Even if he takes you to a jazz show first and then buys you a cup of coffee. Even if he fills the pages of your notebook with his favorite travel recommendations and teaches you local slang. Even if he brings you directly into said friend’s living room. Those Montecristos aren’t real, damnit.