The wheels of my plane lift off the ground, my stomach drops into my shoes, and through the window, I watch Los Angeles International Airport drop away. I’m off. My next adventure has begun—and this one’s special.
I’ve taken a lot of flights in my life, but not like this one. At the other end area city and a country that have been locked away from Americans like me for over half a century.
I’m on the way to Havana, and I honestly can’t quite believe it.
Welcome to Cuba
Take a look at Cuba on a map. You’ll notice it’s really, really long. You don’t go around Cuba—you go across it. It’s 15 provinces cover nearly 40,000 square miles, and it’s an incredible 750-mile journey from one end to the other.
And I really do mean “incredible.” Lonely Planet describes it perfectly—Cuba is “old-school cool”.
Havana’s streets and buildings are so iconic they need little introduction—but the rest of the island is just as appealing. It’s neither touristy nor backwater-remote and features an amazing variety of landscapes, from savannas and tropical plains to mountainous coastlines and picture-postcard Caribbean beaches. Many of its towns and cities are centuries old. It’s located at the edge of one of deepest sea trenches in the world, and the coastal sea life is beautiful and unique.
So, banish any expectations that you’re going to “see Cuba,” unless you’re planning to actually move here and take your time exploring its wonders. This island is far too big to see in one short trip.
It also has a steep learning curve for new visitors. That’s what I’m a little nervous about, as I feel the plane start to descend. But thankfully, I’ve done my research.
Normally I’d say you can get away with limited knowledge of the place you’re traveling to. Normally I’d say you could improvise, learn things first-hand, make it up as you go.
But not with Cuba.
A solid knowledge of the way Cuba works is vitally important for new visitors. This is still a country that doesn’t look kindly on travelers straying outside the rules, lacking the right paperwork, and getting into any kind of bureaucratic trouble that’s entirely avoidable with a bit of advance planning. If you decide to improvise, this beautiful, welcoming island can quickly turn into a real hassle.
Tips for Traveling to Cuba:
- Credit cards and other bank cards are rarely accepted—and you can even have access to your account restricted by your bank because Cuba-based scams are so common.
- Under Cuban law, every foreigner must pay for their accommodation unless they are good friends with a local (which has to be proven with the right documentation, photographs etc).
- If you take dollars and intend to exchange them upon arrival, expect to lose money—there’s a 10% penalty on top of the normal exchange rate, dating back from 2004 when the American dollar was officially taken out of circulation by the Cuban government. There have been recent talks to drop the 10% charge, but right now, it’s still in effect.
- Frustratingly, it’s hard to acquire Cuban currency outside of the country, so you’ll probably have to bring dollars anyway.
- There are two national currencies: the Cuban Convertible Peso (CUC), and the Cuban Non-Convertible Peso (CUP). At the time of writing, in mid-2017, $1 will get you exactly one CUC and 26.5 CUPs. Learn the difference if you want to avoid getting shortchanged by scammers or prevent yourself accidentally handing over a CUC instead of a CUP.
- All visitors to Cuba must have travel insurance, and you may be asked to show proof of it.
- Internet access is far from guaranteed and should not be expected, although WiFi is becoming slightly more common as the economy shifts to cater for tourists. That said, a trip to Cuba might be a good chance to disconnect and go off the grid for a little while.
- You can now import up to $400 of goods from Cuba back to the U.S. (including up to $100 of Cuban cigars). But beyond that, the authorities are leery of foreign entrepreneurial and commercial tourism activity in the country outside of strictly enforced boundaries.
- As always, beware of scams and faked-up “authentic” experiences. (This is a good reason to take a reputable tour—they’re wise to the wrong kind of “self-employed commercial activity,” and will steer you away from the crooks and scammers.)
Of course, all this is presuming you even get into Cuba in the first place. And if you’re a United States citizen, that’s still a tricky business.
Can Americans Travel to Cuba?
For decades, the answer has been an emphatic “no” (not legally, anyway). But thanks to the Obama administration easing restrictions in 2014, this fabulous country is finally opening up to American domestic travelers like me.
Americans can now fly directly to Havana (like I’m doing right now) but it’s the early days in the great thawing of relations between Cuba and the U.S., and the reality of travel to Cuba remains messy.
That’s why I’m taking this trip. I want to test the process for myself, explore a few of the sights, and find out firsthand what it’s like to travel to Cuba as an American.
The first step is learning the most important rule of all.
Dear Americans Traveling to Cuba: Remember, You’re NOT a Tourist
Technically speaking, tourism to Cuba from the United States is still as illegal as it ever was.
However, I'm here on an “educational trip,” which means I’m not technically here as a tourist. This is how Americans like me can legally travel to Cuba.
The 2014 loosening of sanctions was accompanied by a new ruling on the types of trips American citizens were allowed to take into Cuba. There are now 12 categories:
- Family visits;
- Official business of the U.S. government, foreign governments, and certain intergovernmental organizations;
- Journalistic activity;
- Professional research and professional meetings;
- Educational activities;
- Religious activities;
- Public performances, clinics, workshops, athletic and other competitions, and exhibitions;
- Support for the Cuban people;
- Humanitarian projects;
- Activities of private foundations or research or educational institutes;
- Exportation, importation, or transmission of information or informational materials; and
- Certain authorized export transactions.
In the words of U.S. Senator Jeff Flake, “almost every American should be able to travel to Cuba under one of these categories.”
However, the one I recommend you focus on is (5)—an educational trip. To be eligible, you have to show evidence that you’re planning to meet the locals and follow a varied cultural itinerary.
If you’re booking your trip without using a tour operator, you’re going to have to work really hard to assemble an itinerary that meets these requirements.
It can be done. But it’s also an enormous headache.
The other huge benefit of taking a tour is the traditionally obvious one: you’ll be guided towards lots of amazing stuff. Many travelers visiting Cuba independently never see much of what the country has to offer, due to poor travel planning and a travel infrastructure that’s appropriately lacking.
Sadly, it’s all too easy to take a flight to Havana, go out drinking in Havana, bake yourself brown on the pristine beaches of Varadero, and see nothing of the real Cuba. (That’s not an adventure. That’s a missed opportunity.)
Thankfully, this itinerary will get me up close and personal with the best of Cuba—it's a tour that's designed specifically for solo travelers in their 20's and 30's. I’m skipping the big, soulless hotels and staying in privately-owned bed & breakfasts (known as Casa Particulars) as part of the tour package, and I’m heading out of Havana, to cigar-making Viñales, and the well-worn streets of Trinidad.
Before You Travel to Cuba, Learn Its Fascinating, Frustrating History
My 737 drops toward Havana. Butterflies flap in my stomach. I know I’m entering a very different Cuba than the one I learned about growing up in the States—but the history is strong here, and just a few years ago, this trip would get me arrested.
In 1960, Fidel Castro’s new government nationalized American-owned oil companies within Cuba and refused to compensate their (former) American owners. In response, the United States imposed a fiercely aggressive trade embargo, essentially locking the country away from the reach of American businesses, including tourism.
For fifty years, the only way into Cuba if you were an American tourist was indirectly and illegally.
After the fall of the Soviet Union, Cuba’s Communist government started to encourage self-employment—but it wasn’t really until 2011 that the first Cubans really started to embrace homegrown entrepreneurship. With Raul Castro as the ruling power and Castro taking a backseat, combined with an easing of restrictions for self-employed workers, Cuban nationals (mainly in the big cities) began to open their homes as businesses.
Leaving behind relatively badly-paid jobs in local government, many people have opened B&Bs and restaurants to cater for the increasing numbers of “educational travelers” (henceforth referred to as tourists).
The average Cuban working for the government makes the equivalent of $10 per month. Many of these entrepreneurs make well over that in a single day. This means those who own restaurants or rent an apartment are often far wealthier than the doctors and lawyers in Cuba.
The Cuban people have gotten a taste of capitalism over the last several years, and quite understandably, they want more. Equally understandably, the government remains defensive—but things are improving all the time.
For a street-level view of what it means for locals to be self-employed in Cuba, read this lengthy but fascinating piece.
It’s an exciting time to travel to Cuba—if you know what you’re doing, of course.
Scenes From a Beginner’s Travels to Cuba
My nine-day tour focused on the side of the island west of Havana—starting in the capital, moving into the green mountains and tobacco plantations of Viñales, and stopping off in the beautiful colonial-era town of Trinidad before circling back to Havana for the flight home.
As is befitting for an education-visa-based trip, this tour was packed with fascinating activities. You get the chance to roll cigars, cook local food, hike the hills, snorkel off the coast and even have a quiet moment with Che Guevara at his mausoleum in Santa Clara. I couldn’t have asked for a better introduction to this unique, complicated country.
But however you decide to enter Cuba, don’t expect to be able to wander off-script like you would as a normal tourist—because remember, you’re not a tourist, right?
Havana is Effortlessly Cool
Wandering the streets of Old Havana is like wandering through an archived version of the 1950’s.
I know that sounds trite. But wait until you’re here, watching the old Detroit classics roll up and down the streets as if time has frozen.
The buildings and roads in Havana Vieja tell the story of Havana’s history. Once a beautifully-maintained and economically thriving city, it’s clearly suffered over the last 60 years. Buildings lie abandoned and neglected alongside classical, still-lovely architecture. The cars tell a similar story—but the oldest American cars are a part of the charm and character of Havana. It wouldn’t be the same without them.
There is a welcoming energy in the streets of Havana, and happiness on the faces of the locals I meet. They seem kind and proud. Their tough, good-natured Cuban spirit shines through, and it’s utterly charming.
To see Cubans letting their creative side out, get yourself to Fusterlandia, a suburb on the outskirts of Havana that’s covered in brightly-colored tile art (if you’re familiar with Rio de Janeiro, imagine the Selaron Steps on steroids).
It’s the work of Jose Fuster, a local artist determined to brighten up this formerly impoverished neighborhood. (Admission is free, but if you want to make a contribution, there’s plenty of artwork for sale.)
Viñales is Surprisingly Mountainous—and it Smells Great
Just a few hours outside of Havana, you’ll find the sprawling mountain region of Viñales, with enormous hump-backed limestone hills more suggestive of Thailand or Vietnam than the lush plains you might be expecting from somewhere only 90 miles from the Florida Keys.
Most travelers come to Viñales for the cigars.
At a tobacco plantation, I watch a young man wrap tobacco leaves into cigar shapes, blindingly fast. It’s surprisingly uncomplicated-looking, but I’m not seeing the full story here. Many Cubans prefer to dip their cigar in honey to give it a more complex and tastier flavor (a tradition made famous by Cuban revolutionary Che Guevara).
Along with tobacco, this whole region makes its living from fruit, vegetables, that famous Cuban coffee, and fish. In 1999, the whole valley became a UNESCO World Heritage Site—and it’s not hard to see why.
This is the other Cuba, well away from Havana and still working out how to make the most of new tourism opportunities. It’s a big country, but tourism is usually confined to the cities, missing the rolling plains that make up most of the land, and the mountain ranges along its spine (particularly the Sierra Maestra in the southeast).
Trinidad Is A Handsome, Enchanting Colonial Town Built For Your Feet
I walk alone through partially lit streets, tripping occasionally on the uneven cobblestones because I’m drawn by the sights and not concentrating on my feet. Children play in the distance. Stray dogs trot past. Music booms. It’s a hot day, but the colorful colonial architecture is giving me plenty of shade to hide in.
If long, sinew-stretching walks are your thing, the colonial town of Trinidad will tick all your boxes.
Sure, there are beaches and SCUBA diving lessons to take in Trinidad. There are salsa lessons, waterfall hikes, nightclubs, and museums aplenty.
But this is a sleepy corner of the Caribbean, and sometimes all you want to do is allow yourself to be led by your feet—and I recommend you put aside the time to do exactly that.
Cuba Wants Americans to Come and Explore!
This country is amazing. From the yesteryear architecture and road traffic of Havana, across the rolling tobacco fields of Viñales and through the labyrinth of cobbled roads called Trinidad, everything I saw felt like an invitation to see more.
Yes, there are challenges to overcome—but this country hasn’t been so open to American visitors for half a century, and if you pick the right people to guide you, it’s far less of a hassle than you’d expect from reading alarmist or over-cautious reports in the news media.
Cuba is wide open right now. And it’s waiting for you.
A Word On Availability
While I work hard to keep my posts up to date, the situation for travel to Cuba for Americans is a hot topic right now and possibly subject to change.
Just a few days before this post was published, the Trump administration announced it was considering imposing tighter restrictions on travel to Cuba.