Answers to Every Question You Might Have About Traveling to Cuba

What you need to know to book and plan your trip to Cuba.

Answers to Every Question You Might Have About Traveling to Cuba

Holly Wilmeth

As most travelers are well aware, for the first time in 50 years, it’s possible to fly from the mainland United States directly to Cuba. No longer do travelers have to book a charter flight through a travel agent or do the dance of flying to Cuba via Cancun or Canada. That translates to more money in your pocket—and more time on the ground.

The reality is that planning a trip to Cuba is complicated: The visa process is fuzzy (although not as challenging as you might think), hotels are expensive, Internet is not a given, and money is a puzzle. If you want don’t want to sweat over it, put your travels in the hands of an experienced travel consultant, such as Lauren Maggard with Jet Set World Travel, who has been planning bespoke trips to Cuba for the past seven years. Outfitters can also cut through the red tape: Both Insight Cuba and Intrepid offer off-the-beaten path group tours of the country.

However, if you want to plan your own trip (yes, it’s possible) or simply want to understand the nuts and bolts of traveling in Cuba, here’s what you need to know.*

Where can I go?

On July 28, JetBlue announced that it would launch its inaugural flights from Fort Lauderdale to three Cuban cities (Camagüey, Holguín, and Santa Clara) on August 31, making it the first American airline to kick off its commercial flights. To celebrate (and win travelers away from competitors), the airline dropped ticket prices to $99 each way. You’ll have more options in early September: Six airlines—including JetBlue—will offer flights to nine Cuban cities, with direct flights to the capital of Havana expected to start in November.

The bulk of the flights—many of them dailies—will depart from the East Coast, including four Florida cities (Miami, Tampa, Fort Lauderdale, Orlando) although there is one West Coast route from L.A.

How do I get a visa?

Getting a Cuban travel visa, called a tourist card, is easier than you might think. If you travel with an outfitter, or book via a travel agent, they’ll take care of it for you. But they are relatively simple to acquire on your own. A step-by-step guide:

1. Book your plane ticket: When you purchase your ticket, you’ll have to choose from 12 approved categories of travel. Most travelers will fit best in the “people-to-people” educational category, which sounds daunting, but—as of last year—really just requires you to visit cultural sites and keep a “log” of your travels (see #3). And, yes, If you fly commercial, you can use miles to purchase tickets, and you’ll accrue miles on every flight.

2. Apply for your visa: Once you’ve purchased your ticket (and it must be a round-trip ticket—no one-way rides), it’s time to think about your visa. Applying through a third-party operator like Cuba Travel Services (CTS) is easiest. (American Airlines has partnered with CTS to connect travelers with visa applications 30 days before they travel.) Visas through this service cost $85, take at least four weeks to process, and can either be FedExed to your address or picked up at your departure airport’s will-call. If you’re flying through Mexico or Canada, visas can be purchased in the airport or on the plane for $20 cash. (It’s not yet clear if that option will be available to American travelers on the new, direct commercial flights. If in doubt, check with your airline.)

3. Log it: If you’ve applied for a people-to-people license, keep all of your receipts and a diary of where you went (including cultural sites like museums and national landmarks) and who you spoke to in the off-chance you get audited by the Cuban government after you return to the United States (which, our sources say, is almost laughably unlikely).

What do I need to know about the flight itself?

1. Mind your luggage: The current weight restrictions for travelers flying to Cuba (on a charter flight) are 44 pounds for checked luggage (but you can pay $2/pound to go over) and a 20 pounds for carry-on. It’s not clear at this time if that will change.

2. Check in (extra) early: You may be required to sign an affidavit at the airport.

3. Have your credit card at the ready: There may be a Cuba departure tax of $25, which you’ll be able to pay by card.

4. Keep an eye on your email: Watch for any last-minute flight schedule changes. Although routes have been tentatively approved by the DOT, a representative for American Airlines said it’s possible that times will shift slightly, once commercial flights get that final stamp of approval.

*Note to travelers: Although everything appears to moving smoothly, direct flights are still subject to final DOT approval . . . which means things can still change. But we hope not.

What if I want to cruise there instead of flying?

You definitely can! Here are a handful of your options:

1. For do-goodersFathom, the impact-focused sister brand of cruise giant Carnival, was the first company allowed to sail for Cuba (the first cruise launched earlier this year). During the weeklong voyage, the 704-passenger ship stops in Havana, Cienfuegos, and Santiago, while immersive “people-to-people” focused excursions color the journey. Starts at $2,095

2. For extroverts
Starting in January 2017, small-ship cruise line Grand Circle will offer an 11-night Cuban journey that stops in seven vibrant cities. “Local” is the emphasis on this itinerary: Daily excursions include meetings with Cuban baseball players, lunches in private homes, and even casino (Cuban salsa) lessons. Starts at $7,095

3. For sailors with a taste for luxury
On its 11-day land-and-sea journey around Cuba, travel outfitter Abercrombie & Kent places a high emphasis on style. Passengers arrive in Havana via chartered jet and spend the remainder of the trip cruising around the island in a 58-person luxury sailboat. Educational lectures and classes aboard the ship supplement immersive tours in Havana, Santiago, Trinidad, and Punta Frances. Starts at $9,995

4. For nature-seekersThe 11-day land-and-sea journey with National Geographic Expedition covers many of the same cultural sites as other tours. But that’s only half of the experience. Passengers are given the opportunity to speak with Cuban naturalists about the island’s unique ecosystems, as well as to go diving or snorkeling with local preservationists. Starts at $9,500

Do I have to get special health insurance?

According to all the legalese, the Cuban government requires travelers to show proof of insurance to enter the country. U.S. policies don’t cover Cuba, but you can purchase inexpensive plans through reputable insurers for as little as $2-$3/day. You can also purchase a policy at the airport once you land in Cuba for about $25. OK, now that we’ve done our legal due diligence, we’d like to add that none of the AFAR staffers who have traveled to Cuba (some of whom have traveled there multiple times) has ever been asked about insurance. So do with that what you will.

How far ahead should I book?

At least six months in advance if you want to book a hotel instead of a casa particular. Hotels are filling up fast—and prices are rising.

Once I’m there, how do I get around?

It all depends on where you are and where you want to go.

I want to fly from one end of the island nation to the other: You have one option, Air Cubana, which offers both international and domestic flights. A two-hour jaunt from Havana to Santiago de Cuba starts around $250.

I want to take a bus from city to city: Viazul’s clean, air-conditioned buses are one of the cheapest ways to travel longer distances in Cuba. For example, the 145-mile trip from Havana to Cienfuegos costs about $20—and about 5.5 hours of your time.

I want to take a train: Our Cuba pros say: Just don’t. Unless you like sloooooooow travel. If that’s your speed, you’re looking at 15-20 hour ride (b.y.o. food and beverage) to get from Havana to Santiago de Cuba with a schedule that’s as capricious as the wind. The good news? It’ll only set you back $43.

I want to have my own wheels: It’s doable—and fun!—although expensive and requires patience (road signs are minimal and highways aren’t lit at night). Average rental car prices range from $70-$150/day, the cars are small (think KIAs or a Geely, a goofy-looking car that you should definitely google), and gas is close to $5/gallon. You can book in advance through Air Cubana or a third-party operator like Cuba Travel Services. Keep in mind that you can pay for your car in advance with a credit card, but you will most likely have to pay for insurance and other extras in cash. Bring more than you think you need.

I just want to get from Point A to Point B in Havana (including the airport): Take a peek at your options in the slideshow below.

Where should I stay?

Though there are no major U.S. hospitality chains in Cuba (yet), there is certainly no shortage of comfortable hotel options for travelers looking for something streamlined and familiar. If you chose to go the hotel route, however, keep in mind: Last-minute doesn’t really fly here. Most require that guests book at least two nights prior to their stay, but we recommend making reservations far, far earlier than that (like six months earlier). Rooms are in major and constant demand, especially during the high seasons (November to March, and July to August).

For a Havana spot with some history, there is always the Hotel Nacional de Cuba, which has been open since 1930. If you’re on the hunt for fantastic views and modern amenities, however, we like the Saratoga, as well as Parque Central.

Casa Particulares

Before renting out a room in a foreign city was cool, Cuba had casa particulares. Previously, the only accommodations available to travelers were large state-owned and operated hotels. But in 1997, the government passed a law that allowed Cubans to turn their private residences into bed and breakfast–like homestays. These days, thousands of houses around the country welcome travelers with vibrant and homey places to rest their heads.

The experience of staying in a casa particular offers up a taste of local life that you would otherwise miss in one of the larger hotels. Since the system is less than streamlined, however, what you get and what you pay depends on where you stay—though most prices tend to hover at around $40 a night. Some casas are villas, some are full apartments, and some are simply shared rooms. Likewise, the amenities can vary greatly; some offer breakfast, lunch, and dinner for an added fee, some have bartenders on their rooftop terraces, and some are relatively bare bones.

There are plenty of ways to book before touching down in Cuba (which, given the high demand, is strongly recommended). In addition to the recently unbanned Airbnb Cuba, there are a few websites, such as My Casa Particular and Cuba Booking Room. If you’re a risk-taker, you can also wing it—many hosts stay offline and prefer to gather guests by advertising their homes at busy transportation hubs. Keep in mind that not just anyone can be the proprietor of a casa particular—homes that have been registered with the government, as required, are identified by a sign outside. Also, it’s not unheard of for travelers to book one casa online, only to show up and be led to another. Don’t be alarmed; it’s not entirely a scam. But you just might not get what was advertised.

How do I pay for things?

Once you land in Cuba, your credit cards are useless for nearly every purchase. Bring lots of cash and exchange it at the airport. You’ll get hit with a hefty exchange fee (at least 10 percent), but there’s no way around that. Just estimate how much you’ll need and carry back-up $20s in the event your predictions were off.

The money you’ll get from the vendor will be in CUC, pronounced like “kook” and often referred to as dollars, as well. The easy part is that one CUC is equal to one U.S. dollar. The not-easy part is there is an additional currency to watch out for: pesos.

CUC are generally used only by tourists and locals purchasing nicer things. Meanwhile, most Cubans carry pesos (CUP), which you need to divide by 24 to convert to USD. You probably won’t encounter these unless you eat at a hole-in-the-wall restaurant or buy a bus ticket, as you’ll likely get change back in pesos if you pay with Cuban dollars. To get rid of them, you’ll probably have to make another similar purchase because most hotels, nicer establishments, and currency exchange offices will refuse to accept pesos.

What about the ’ol Internet dilemma?

Honestly? Your best bet is to think of your time in Cuba as an unofficial digital detox. Verizon customers are the best off, although Wi-Fi is spottily available.

Is it safe to drink tap water?

No, unless the home has a well (this goes for ice as well). It’s relatively easy to find bottle water: Keep an eye out for TDR, Cimex, or El Rapidito stores. In Havana, you can buy large water bottles from a stand on the bottom floor of the department store at the corner of the Malecón and Avenida Paseo.

How do I buy water and other indispensables?

There are no one-stop-shop places like Walgreens in Cuba. The quickest route to basic necessities in Havana is heading to the shops in a high-end hotel. You’ll be charged a lot. For more reasonable prices, try the local department store mentioned above (it’s at the corner of the Malecón and Avenida Paseo). Sundries you may have forgotten at home or avoided packing, like toothpaste and sunscreen, can be found upstairs in the grocery. Sorry, Crest and Coppertone devotees: You’ll probably have one choice for whatever you need and it will likely be either in Spanish or an unfamiliar Eastern European language.

Can you give me a flirting 101?

Flirtation is second nature to Cubans. As a New Yorker visiting Cuba for the first time, I was tempted to flip the bird at several cat-callers on the streets of Havana. But after numerous visits to the island, it’s become clear that the playful attitude of Cubans is their way of coping with what can be an arduous day-to-day. My advice? Have fun with it! As long as they’re not aggressive, there’s nothing wrong with an occasional “where you from, mami?” or a twirl on the dance floor.

That isn’t to say there aren’t weirdos out there. Sex tourism is real in Cuba—both men and women, especially from Europe, have created demand for paid partnership—so make sure your new friend isn’t expecting cash or a visa from your romancing. Solo women should use common sense: Don’t bring strangers to your Airbnb, don’t go out alone with a big group of guys, and don’t allow anyone to pressure you to pay for all of the drinks. Most Cubans are very excited to make a yanqui friend and will quickly make you feel welcome. And you never know where that might lead! —Alex Palomino

What do I need to know as an LGBT traveler?

LGBT progress in Cuba is hard to qualify. On the one hand, trans politicians have been elected to office, and the government offers free gender reassignment surgeries. On the other hand, gay men were persecuted in concentration-style camps in the ’60s and “publically manifested” homosexuality, however that may be defined, remains illegal. Most locals will tell you that they have no problem with gay people—quite the opposite, that they accept them. But if you are traveling with a same-sex partner, it’s a good idea to avoid physical contact in public. You’ll be hard-pressed to find local same-sex couples who are affectionate on the streets.

As for gay bars, they exist but mostly serve for tourists. Gay locals often attend parties that are promoted by word of mouth instead. The same goes for gay male dating apps: Sign on and you’ll find a grid of Brits and Australians on vacation.

What if something goes really, really wrong?

Head for the reopened American embassy in Havana. You can register before you travel, and it’s worth walking by to snap a photo even if you don’t need to go through the doors.

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