Here’s the catch with those new U.S. flights to Cuba (and how to get there anyway)

Cuba Capitol
Update on July 12, 2016: The U.S. Department of Transportation has awarded several airlines with flights to Havana and the rest of Cuba. The story has been updated to reflect recent news.

Update on March 15, 2016: The Obama administration has further relaxed the travel ban on U.S. citizens. While Cuban tourism is still illegal, Americans can now take part in people-in-people trips independently, without joining a certified tour group. Travelers will still need to visit for educational purposes, and keep records of the trip for five years, but it’ll be difficult to enforce, i.e. you probably won’t get in trouble for relaxing on a beach. The following article has been edited to reflect recent changes.

On February 16, 2016, the United States and Cuba signed an aviation agreement that could see up to 110 scheduled commercial flights between the two countries. Most U.S. carriers expressed some form of interest in offering service, and some rushed to the front of the line. Even President Barack Obama, who’s pushed for easing of sanctions, announced that he plans to visit the island nation in March. In July, the U.S. Department of Transportation gave approval to eight airlines to service Havana from various cities across the U.S. The DoT had already awarded six airlines with routes to other cities in Cuba, in June.

So, can you finally put Cuba at the top of your travel destinations? Well, not so fast.

Despite the easing of sanctions since the U.S. restored diplomatic relations in 2015, many travel restrictions for U.S. citizens still apply – chiefly you still cannot yet visit Cuba as a general tourist. While Alaska, American, Delta, JetBlue, Southwest, United and a few smaller carriers have all been awarded routes, they still need to negotiate deals with the Cuba’s aviation administration, and the first flights may not start until the fall.

But the opening of commercial air traffic is the latest indication of thawing tension between the two countries. The trade embargo has limited commercial flights since the 1960s, but today, some U.S. airlines are allowed offer chartered direct flights. But to hop on one, you need to meet the 12 legally permitted categories of travel, set forth by the Department of the Treasury’s Office of Foreign Assets Control and explained below. Those who don’t meet these qualifications often find alternative methods of visiting Cuba, often connecting in another country.

Even visitors who are permitted to enter Cuba legally face pricey airfare. But the aviation agreement could solve that as airlines compete for customers’ business (although the travel embargo rules still apply, and the number of flights will be capped).

Once U.S.-Cuba relations are fully restored, you can expect the tourism industry to explode in this once forbidden destination. When – and if – that happens is still up in the air. The outcome of the presidential elections could affect the future of U.S.-Cuba relations.

Ready to go now? Here’s what to know about traveling to Cuba.

Why would you want to go?

Cuba has a rich culture and history, and is home to nine UNESCO World Heritage Sites. Some people argue that now is a good time to visit before it opens up to general tourism and U.S. commercialism. But, as mentioned, getting there isn’t straightforward or cheap.

Getting there

Before the U.S. and Cuban governments reached the aviation agreement in February, some anxious airlines had already indicated they plan to apply to fly the routes. American Airlines, which flew approximately 1,200 chartered flights to Cuba in 2015, said in a statement it “looks forward to submitting a Cuba service proposal to the Department of Transportation in the coming weeks,” and plans to make its Miami hub the primary gateway, with 10 flights a week to start. With the huge Cuban population in Miami, it’s easy to see why American is eager to offer flights. Alaska, Delta, Dynamic, Eastern, Frontier, JetBlue, Silver, Southwest, Spirit, Sun Country, and United also released similar statements and proposed routes.

Cuba Flight

The agreement calls for 110 flights to be allocated to U.S. carriers, but only 20 will be to Havana, Cuba’s capital. The rest will be divvied among nine other airports.

Currently, American, Delta, and JetBlue are among a handful of U.S. carriers that offer chartered flights to Havana, and they must be booked through a charter provider. You can book a flight independently through, which is currently the only online travel website to sell charter flights to Cuba. The airlines themselves do not offer the option of booking through their websites, and all travel must fall under one of 12 categories (see below).

Since the aviation agreement, the DoT has approved several routes. American Airlines, Frontier Airlines, JetBlue Airways, Silver Airways, Southwest Airlines, and Sun Country Airlines were awarded routes from Miami, Fort Lauderdale, Chicago, Minneapolis/St. Paul, and Philadelphia, to nine Cuban cities: Camagüey, Cayo Coco, Cayo Largo, Cienfuegos, Holguín, Manzanillo, Matanzas, Santa Clara, and Santiago de Cuba.

The more heavily contested routes, however, are to Havana. Alaska Airlines, American Airlines, Delta Air Lines, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, and United Airlines will service Havana from Atlanta, Charlotte, Fort Lauderdale, Houston, Los Angeles, Miami, Newark, New York City, Orlando, and Tampa and Havana.

Valid entry

Until general tourism is permitted, currently visitors must have a legitimate reason for entering Cuba. Per the U.S. Treasury, they are:

  • Visiting family
  • Humanitarian projects or to provide support to the Cuban people
  • Official business of the U.S. government, foreign governments and certain intergovernmental organizations
  • Journalistic activities
  • Professional research
  • Educational activities by persons at academic institutions
  • People to people travel
  • Religious activities
  • Public performance, clinics, workshops, athletic or other competitions and exhibitions
  • Authorization to provide travel services, carrier services and remittance forwarding services
  • Activities of private foundations, research or educational institutes
  • Exportation of certain Internet-based services

Eased sanctions have made travel to Cuba possible for more U.S citizens, but that doesn’t mean everyone is allowed to enter freely. Even if you meet the criteria, you still need to apply for a visa. Fortunately, it isn’t expensive, and charter agencies can handle the application on your behalf.

If you want to explore Cuba now, but you don’t have any actual reason other than personal enjoyment, your best bet is to look at the person-to-person travel option. You can sign up for a supervised cultural tour with a set itinerary (via a certified agency), or go on your own. If you go with the former, on the tour, you get to see the country’s landmarks and interact with residents from all walks of life, and tour packages are all inclusive minus airfare and other fees. National Geographic Expeditions is one tour provider, but it’s pricey: Tours start at $6,000, and 2016 tours are already waitlisted. Another option is Exodus Travels, which offers tour options that start at around $1,300.

Cuba has a rich culture and history.

Another option is to fly through a gateway, such as Canada, Mexico, or the Bahamas, which could sometimes be cheaper, albeit longer. Legally, your travel still needs to fall under the aforementioned categories before you’re issued a visa. However, because passports aren’t stamped and you only need to sign an affidavit stating your travel meets the requirements, some visitors have been able to enter Cuba through this route. With that said, recent easing of person-to-person restrictions will make this option less attractive, in our opinion.

Since U.S. citizens aren’t required to seek permission beforehand, it’s easier to slip under the radar. However, if someone is audited and found to have entered illegally, it could result in a heavy fine or even imprisonment. We recommend finding a legitimate reason (some of the 12 categories are vague enough that you can find a legal purpose) and avoid the trouble. However, the relaxing of rules is making it harder to enforce.


Once you land, don’t expect your smartphone to work. Cuba’s cellular network is restricted to 2G – no data, just voice and SMS. But you will need a Cuban SIM card and an unlocked GSM-based “dumb” phone. Verizon and Sprint customers have roaming service for its customers, but it’s costly.

Since you won’t be able to pull up information on the fly, you will need to carry paper documents, including maps.

Wi-Fi hotspots are limited, as is Internet access, in general (although that’s changing). If you do find one, it would most likely be a pokey dial-up connection. If you are staying in a hotel with reliable access to the Internet, it’s best to get the information you need before heading out. And if you’re lucky to find fast Internet, you could access Netflix to kill some time, but why would you when you have a whole country to explore?


Although American Express and MasterCard announced theirs cards can be used in Cuba, it is not widespread. Few businesses in Cuba are able to accept credit or debit cards, and the cards have to be issued by a bank that can process those transactions (the list does not include any major banking institutions).

Cuban Cars
Jeff Zurschmeide/Digital Trends
Jeff Zurschmeide/Digital Trends

Cash is king, but because the Cuban peso isn’t traded globally, you can’t exchange for it stateside. Plus, U.S. dollars face a 10-percent penalty and 3-percent fee when exchanged. To avoid the penalty, you could exchange your dollars to euros or another currency that’s accepted first (check the exchange rates to see where you can get the best deals), and then exchange those funds for Cuban pesos. Because of the penalty and fee, it’s unlikely Cuban businesses will accept U.S. currency directly.


Hotels are common in Cuba, but they aren’t abundant. Even though U.S. citizens are banned from vacationing there, Cuba has a booming tourism industry and receives visitors from Europe, Canada, Latin America, and even China. It’s reported that 3.5 million tourists visited Cuba in 2015, and it’s expected to grow. This places a strain on Cuba’s infrastructure.

Once U.S.-Cuba relations are fully restored, you can expect the tourism industry to explode.

If you aren’t booking through an agency, one colorful option is to search for “casas particulares,” or private homestays, via Airbnb. Last April, the company announced it was bringing the sharing economy to Cuba, since Cubans are permitted to rent out to tourists per a 1997 ruling. While these accommodations are modest, you get to interact with ordinary Cubans who would most likely share their stories and tips, so you can get the most out of the trip – through their eyes. After all, that’s the appeal of Airbnb.

Getting around

Public transit in Cuba could be considered antiquated. There are horse carriages and pedicabs that will get you around if you aren’t pressed for time. Buses can be overcrowded, and there are ferries that travel between ports. For the most part, you’ll most likely rely on walking or catching a taxi. Fortunately for you, it will probably be the most unique taxi you’ll ever ride in.

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