Eight Secrets You Need to Know Before Traveling to Cuba

Cuba's Calling

Photo by Benet J. Wilson

Editor's note: This post has been updated to reflect the new proposed travel rules to Cuba announced by President Donald Trump on June 16, 2017.

In 2016, the U.S. Department of Transportation approved six domestic airlines to begin scheduled flights to Cuba from Miami, Fort Lauderdale, Chicago, Philadelphia, and Minneapolis/St. Paul. CheapAir.com has offered eight tips for travelers who still want to visit the island nation.

The carriers that won service to Cuba are American Airlines, Frontier Airlines, JetBlue Airways, Silver Airways, Southwest Airlines, and Sun Country Airlines. But since that announcement, Silver Airways and Frontier Airlines have ended their flights to Cuba, while other carriers are cutting some flights.

The five U.S. cities that will receive new scheduled service to Cuba are Miami, Fort Lauderdale, Chicago, Minneapolis/St. Paul, and Philadelphia. The nine Cuban cities are Camagüey, Cayo Coco, Cayo Largo, Cienfuegos, Holguín, Manzanillo, Matanzas, Santa Clara, and Santiago de Cuba (see more details here). 

Online travel agency CheapAir.com began offering charter flights from the U.S. to Cuba in April 2015. Since then, access to Cuba flights has been expanded, making it much easier for travelers to book their flights a much simpler proposition from virtually anywhere in the country, including:

Alaska Airlines    

LAX to HAV                1x daily


American Airlines    

MIA to Cienfuegos     1x daily

Charlotte to HAV        1x daily

MIA to HAV                4x daily

MIA to Holguin           1x daily

MIA to Santa Clara    1x daily

MIA to Camaguey      1x daily

MIA to Varadero        1x daily


Delta Air Lines             

ATL to HAV                 1x daily

MIA to HAV                1x daily

JFK to HAV                 1x daily



FLL to Camaguey       1x daily

FLL to HAV                 2x daily, 1x on Sat

JFK to HAV                 1x daily

MCO to HAV               1x daily

FLL to Holguin            1x daily

FLL to Santa Clara      1x daily


Southwest Airlines   

FLL to HAV                 2x daily

TPA to HAV                1x daily           

FLL to Santa Clara      1x daily

FLL to Varadero         2x daily


United Airlines      

Houston to HAV         Sa

EWR to HAV              1x daily

Despite the proposed travel changes, the actual process of getting to Cuba has been streamlined and made simpler in terms of logistics. Procurement of the Cuba travel card (what many people call a visa) and obtaining Cuban health insurance were confusing for a lot of travelers in the past. Now, these items (as well as the $25 exit tax that you have to pay when leaving Cuban soil) are included when you book your flight with a U.S. airline.

Travelers will still face unique accommodation quirks in Cuba, where the demand for quality hotels does still outpace the supply and standard available. One excellent accommodation option is to book casas particulares. Casas particulares are privately run, and therefore a better choice to stay compliant with U.S. rules prohibiting payments to government businesses. You can book them direct on the Internet or through Airbnb.

“It’s human nature that when you’ve been told so long that you can’t go somewhere, it’s exciting when you can go to a formerly forbidden place,” said company president Jeff Klee. “Travelers want to get to Cuba before there’s a Starbucks on every corner.”

People who have been there talk about it being frozen in time, said Klee. “It’s one of the few places in the world that haven’t been Americanized, so that is still appealing to travelers,” he said.

“My sense is that the U.S. airlines want to get their foot in the door even though that much demand isn’t there yet,” said Klee. “It still isn’t legal for U.S. citizens to go to Cuba just because they want to go, even though it’s not being enforced much,” he said. 

As long as travelers self-select a valid license, they won’t run into problems. The honor system is still in place and at this point, CheapAir.com isn't hearing of any further reversals in policy at this time. Just be sure to keep an itinerary consistent with your reason for travel, and keep a record of it with you when re-entering the U.S.

Below are the eight steps for travelers who want to travel to Cuba, as shared by CheapAir.com.

1. Qualify yourself for travel. Review the 12 permitted reasons for travel to Cuba and determine which license allows your visit (Under the Trump Administration changes, individual people-to-people licenses are no longer valid).

2. Book your flights. 

3. Arrange accommodations. As more people travel to Cuba, the island’s infrastructure is racing to keep up. CheapAir.com recommends loking at the Cuban version of the bed & breakfast – a Casa Particular, which can now be booked on Airbnb.

4. Decide on an itinerary and determine your transportation needs. For some people, an introduction to Cuba might mean hanging out in Havana for a week. You don’t need a car, since taxis (both official and unofficial) are all you might require for getting around. Having a car in Cuba is worth a splurge if you want to get out of Havana. Travelers can book a rental car from the U.S. The limited number of Cuban rental car companies are in high demand and command a high price, so prepare to spend two to three times what you might spend in the United States for a week.

5.  Plan to bring lots of cash. American banks are still not synced up to the Cuban banking system, meaning no ATM access for U.S. citizens. And most businesses won’t accept credit cards, so make a budget and plan to bring 30-40 percent more in dollars or Euros than you think you’ll need. Also, the Cuban government charges a $25 fee from each visitor upon exit, but most charter flights collect the fee upon departure from the U.S.

6. Research your trip thoroughly. Cuban museums and cultural attractions are set up as they are the world over, so you’ll want to have a plan of attack on how to organize your activities and keep a list of hours of operation and holidays that could affect those plans (you may not have an internet connection there to confirm the hours after you arrive). Keep your receipts for cultural activities to demonstrate your visit was filled with “authorized travel activities.”

7. Take care of the red tape. Travelers need two documents – the Cuban “tourist card” and proof of Cuban health insurance. In some cases, when you buy a direct charter flight through CheapAir, its charter partners will help you procure the tourist card. If you buy a flight that routes you through another country (like Panama or Mexico), you’ll pay for the tourist card in the airport as part of the check-in process. The Cuban government requires travelers to purchase Cuban health insurance. Should a traveler need to see a Cuban M.D., they’ll be covered. Cuban health care is respected around the world and their insurance is under $10 a day. If you don’t have it before you land in Cuba, you’ll be required to buy it in the airport before being admitted into the country.

8. For dining, experience paladar culture. Paladares are “unofficial” restaurants operated by citizens. They used to be quite secretive, and speak-easy style in people’s living rooms. But these days, there is more of a mutual understanding between the government and the restaurants. 

The jury is still out on the long-term relationship with Cuba, but at the moment these seem to be the only policy changes that the government plans to enact. Travelers who qualified under the “individual, people-to-people educational license” and purchased a flight or hotel before the announcement on June 17, 2017, are grandfathered in and can continue with their plans without fear of penalty.

EDITOR'S NOTE: Please follow my travel-related magazines on Flipboard: Best of About Travel, a joint curation venture with my fellow About Travel Experts; and Travel-Go! There's Nothing Stopping You, all about the passenger experience on the ground and in the air. You can also find my travel-related boards on Pinterest and follow me on Twitter at @AvQueenBenet.

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