How to Plan an Unforgettable Trip to a Long-Forbidden Island

It’s more than a trend. It’s a small tsunami.

American travel to Cuba increased by 77 percent in 2015 after Presidents Barack Obama and Raúl Castro signaled a rapprochement in relations between their respective countries last January. Further easements on travel restrictions ahead of Obama's landmark visit to the Caribbean island this March mean that number will only climb in 2016.

Though the embargo remains in place, the most important news for American travelers is that they can now apply for people-to-people travel visas as individuals—a welcome alternative to the supervised group tours that have been the primary legal means of visiting Cuba for years. 

Cue visions of a multicultural melting pot of a country offering unspoiled natural beauty and bottomless mojitos. Pretty much the perfect scenario for a vacation. 

Strike that word!

There are quite a few things Americans need to know about visiting Cuba, and the first one is that their stay will not be an aimless, wander-and-flop getaway. (Ordinary tourism remains verboten.) What it will be, however, is rich in new sensations and enriching encounters.

Whether you're planning to go solo or as part of a group, here are eight rules of thumb to keep in mind as you plan your trip.

1. Tourist is a dirty word.

The foremost thing to understand is that for most Cubans, the words “tourist” and “American,” when shaken and stirred, evoke bad memories. Bitter memories, in fact, of the pre-revolutionary era, when U.S. interests essentially controlled the island’s economy—including rum production, gambling, and other money-laundering businesses that flourished before 1959—and hence its politics. (See "How Mass Tourism Will Change Cuba.")

So the Cuban government—wary of a sweaty, rum-slugging, selfie-snapping norteamericano tourist tsunami—stipulated that most American travel to their island must be for one purpose and one purpose only: people-to-people interactions that deepen one's appreciation for Cuba and its people.

This is why group tours have long been packed with activities that promote cultural learning—such as visits to schools or artist studios—and facilitate encounters with everyday Cubans.

American travelers who wish to travel to Cuba independently can now do so, but they must mark a box on their visa application to denote which of a dozen authorized “people-to-people” travel categories—including visiting close relatives, academic coursework for credit, and religious pursuits—their trip falls into.

The general feeling among those in the know is that it’s “don’t ask, don’t tell” in terms of officials ensuring that individuals meet the people-to-people requirements. But it certainly can't hurt to keep track of personal interactions with locals as well as efforts to learn about Cuban culture and history as you go along.

You'll also need to retain all receipts related to your trip for a full five years when you get home. So there's that.

2. Flexibility is important.

If this seems like a general travel truism, it’s really true in Cuba at the moment.

After more than five decades of communist rule, the Cuban economy is in tatters. Stuff just doesn’t always work. The electricity is out. The restaurant is out of your menu choice. The hotel or B&B you’ve booked into cancels your reservation at the last minute or transfers you to less appealing digs.

In fact, all of the above happened to me last November when I traveled to the island on a group tour. I expected to encounter electrical brownouts, even blackouts. But I was surprised to feel the effects of food rationing so quickly—admittedly, in a very insignificant way—when a café in La Habana Vieja wasn't able to serve me a mojito.

“Mint isn’t always available,” our guide said by way of explanation. Indeed, there was nary a sprig available at the farm market we visited the next day. (Apparently, some bartenders grow their own mint to ensure a steady supply.)

We did, however, get to see the food-rationing system in action: One section of the market presented fruits and vegetables for sale, while a separate area was reserved for locals to pick up their rations of flour, beans, meat, and other staples.

Later, on a group excursion to the beautifully preserved colonial city of Trinidad, it took me longer to accept the fact that our group had been bumped from the nice guest house we’d paid for into a dumpy alternative.

I’m still not sure exactly why this happened (and you probably won’t either, unless you speak fluent Spanish and are adept at reading between the lines), but I shrugged it off, even though my fleabag motel days are behind me.

Bottom line: If you're not willing to roll with unexpected—and often inexpicable—changes, you're probably not going to enjoy your time in Cuba.

3. Cash is king.

As a result of the embargo, only a few banks across Cuba are equipped with ATM machines that allow withdrawals from U.S.-based bank accounts. Likewise, most restaurants, homestays, and hotels—excepting major chains serving international travelers—won’t (or really can't) accept U.S. credit or debit cards, either.

To avoid headaches, either book and pay in advance or bring a mountain of cash to convert to Cuban pesos upon arrival. 

Tip: A 10-percent surcharge is typically applied to U.S. dollars at the exchange counter, so you’ll get better bang for your buck with euros, Canadian dollars, or pound sterling.

4. Group travel has its advantages.

Though independent travel is at last permitted, consider your options carefully before scrubbing the idea of a group trip. In fact, an organized tour may be the best choice for first-time visitors to Cuba, non-Spanish speakers, and those unused to traveling outside of their comfort zone.

Molly Danner, a program director at National Geographic Expeditions, says travelers book with them because “they want to visit Cuba in a meaningful, more immersive way.”

Tour operators not only take care of logistics, they can also avail themselves of long-standing relationships at local hotels and restaurants, thus minimizing "guest turbulence."

Danner points to National Geographic's renowned international experts and knowledgable guides as additional selling points for their trips. In a fast-changing country like Cuba, she says, local guides ensure that last-minute snags don’t morph into disasters.

For more experienced and intrepid travelers, planning an independent trip allows more time for free-form exploration or to simply relax. But that doesn't mean booking charter fights and local accommodations will be a snap. 

If you're looking for something that falls somewhere between a full-on group tour and an independently organized trip, small travel agencies are increasingly cropping up to fill that gap.

Katherine Reifler, a 24-year-old medical student in Chicago, planned her bare-bones trip with a boutique online operator called Locally Sourced Cuba Tours.

Though it was technically a “group” tour, in reality the company simply eased the pain of reserving local homestays and transportation, while Reifler was in charge of her meals and entertainment. “They were incredibly helpful via email,” Reifler says. “[They also] answered all my questions about visas and travel insurance.”

5. Expect—and embrace—the digital detox.

Instagrammers, Snapchatters, and compulsive texters be warned. You will not have cell phone service in Cuba.

Cuban citizens are not allowed to have private access to the Internet. Wi-Fi is nearly nonexistent outside of major hotels, and even there, you’ll need to pay for service (unless you’re a guest with a pass code) and the connection will almost undoubtedly be slow. Internet cafés are available, but rare.

The government has recently set up Wi-Fi hotspots on several Havana street corners and in major tourist centers such as Trinidad. To use them, you’ll need to shell out a few pesos for an official data card.

6. Consider traveling via a third country for better airfare rates.

Until commercial airline service between the U.S. and Cuba resumes in late 2016, travelers are stuck with expensive charters from American soil. 

Even after commercial flights from the U.S. are in place, some experts predict that if demand remains high enough, fares may not be much lower than charter flights (which are currently running at an average of $700 per round trip). Eventually, though, most believe prices could drop by half following the initial surge.

In the short term, though, a good option for bargain seekers is to consider traveling to Cuba via a third country, such as Mexico, where some flights are 20 percent cheaper than from the United States. 

7. Cuban airports can be bottleneck zones.

Upon arrival, strained airport infrastructure and lackluster service thanks to years of communism make for potentially lengthy flight delays and baggage claim lines.

Departures are another story. Passengers don’t have any control over delays—or access to information—as I discovered on my recent trip, when I waited more than three hours for my flight to leave an airport in central Cuba. And since it was a charter, I had no recourse when I missed my connecting flight in Miami.

Lesson learned: Make sure to give yourself at least four hours of time for stateside connections.

8. Keep your mental door open.

Your waitress at the chic paladar (independently owned restaurant) may be an architect, your taxi driver an aerospace engineer. In planned economies like Cuba’s, a high level of education doesn’t necessarily amount to earning more money.

Interesting conversations abound, if you’re open to them (being able to speak basic Spanish helps). Cuba has one of the world’s highest literacy rates—98 percent!—thanks to policies implemented after the 1959 revolution. Everyone goes to school, and arts and music education is readily available to all (hence the vibrant music and contemporary art scenes).

Author Pico Iyer said it best. “For centuries, Cuba’s greatest resource has been its people.” For Americans, traveling to the long-forbidden island brings that sentiment to life, vividly.

Ceil Miller Bouchet is a freelance travel writer based in Chicagoland. Follow her on Twitter and Instagram @CeilBouchet.