How to Travel to Cuba on a Charter Flight

Dec 21, 2015

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Since travel restrictions to Cuba were eased last year, airlines and charter services have connected Havana and the rest of Cuba to cities around the US for the first time in decades. Over the past year, US-based airlines have slowly been rolling out service in the form of charter flights, but this week the US Department of State announced that airlines could begin scheduling regular service, which might launch as soon as 2016.

While there aren’t any regular commercial flights operating regularly between the countries just yet, travelers willing to jump through a few hoops can certainly reach Cuba booking through a charter. You won’t be able to search for a ticket with tools like Google Flights, but you can find independent services flying to Cuban destinations. Moreover, these charter flights aren’t eligible to earn miles, but that could change once regularly scheduled service begins flying to Cuba.

Cuba is more accessible than ever. Photo courtesy of Shutterstock
Cuba is more accessible than ever. Image courtesy of Shutterstock.

At present, there are still a few rules for Americans visiting Cuba. First off, your trip must fall within 12 eligible categories, including family visits or humanitarian projects. Most of the airlines have a complete list with some background on Cuban sanctions located on their websites. In spite of these travel requirements, Cuba is still quite accessible and visiting is certainly in the realm of possibility for interested travelers.

If after all of this you still want to visit Cuba from the US, the best place to start is by contacting a charter service. Each company seems to operate a bit differently, but there are quite a few similarities between them. First off, you’ll have to select a service that flies from a city near your home (more on that in a bit). If a flight isn’t operated from your home base, you’ll have to arrange your own travel on a separate itinerary to meet the charter. Most of the flights fly nonstop to Havana, but there are certainly other destinations you may want to visit in Cuba, such as Santa Clara or Holguín.

Holguin is one city connected to the US with charter flights.
Holguín is one city connected to the US with charter flights. Image courtesy of Shutterstock.

It’s possible to search for flights through the individual charters, although it’s a bit different than a normal airline website. Flights are listed in chronological order showing every flight that is operated — think train schedule rather than This means it can be a bit clunky to find exactly the flight you’d like to travel on. Additionally, flights aren’t scheduled too far in advance, so it can be difficult to plan a trip more than two or three months before you plan to travel.

Once you decide on a charter service to use and the particular flight you’d like to fly, you’ll have to complete an application or travel affidavit that must be approved for your visit. Information included in travel paperwork seems to vary a bit, but it mostly asks for the reason of your visit, personal information and legal release forms. This shouldn’t be an issue for most travelers and isn’t quite the barrier it may seem to be.

Many (if not all) of the charter services will process the visa for you. Once this paperwork is approved and you’ve submitted your visa information, planning is mostly over and you’ll just have to arrive at the airport ready to fly!

Traveling to Cuba could become much easier in 2016. Image courtesy of Shutterstock.
Traveling to Cuba could become much easier in 2016. Image courtesy of Shutterstock.

As I’ve said, each charter service seems to have some slightly different rules, so be sure to plan ahead and take note of individual policies to ensure everything goes smoothly before and during your trip. Some services say that this process can take up to 60 days, however, others recommend planning a month in advance of your trip (perhaps more if you’re traveling during a busy season, like spring break). In addition to flights, many of these charter services can also arrange housing accommodations and activities.

Keep in mind that traveling to Cuba on a charter flight can be quite expensive. Tickets in February via Cuba Travel Services on its charter flight between New York and Havana cost more than $800 round-trip, and that’s not including the $85 visa fee. An alternate and more cost-effective method is to travel to the island through a third country, such as Mexico or Canada. Air Canada, for example, has flights bound for Havana departing from Toronto. Aeromexico and Interjet also have flights departing from Cancun. In addition to the rules for traveling to Cuba, the US Department of Treasury’s regulations must be fulfilled for Americans returning home. This includes a $400 limit on souvenirs brought back from Cuba, as well as a $100 limit on cigars and alcohol.

Ultimately, traveling to Cuba is certainly in the realm of possibility for many Americans. While there are a few restrictions, they’re broad and an itinerary can be planned with the rules in mind. For many travelers, the biggest barrier to entry might be the excessive cost, especially for a flight that’s an hour from Florida and can’t be booked with points and miles (at least not yet).

Here’s a list of charter flights to Cuba:

American operates charter flights to Cuba. Image courtesy of Shutterstock.

American Airlines operates 23 weekly charter flights from Los Angeles, Miami and Tampa to a number of destinations within Cuba. At present, travelers are unable to earn or redeem AAdvantage miles on flights to Cuba because they’re charter flights. American’s charter services are flown by four firms: ABC Charters, Cuba Travel Services, Marazul and Xael Charters Inc.

Destinations include:

  • Camaguey
  • Cienfuegos
  • Havana
  • Holguín
  • Santa Clara

Los Angeles (LAX) – Havana (HAV) on American Airlines

Details — American’s charter service from Los Angeles is one of the newest flights to Havana from the US.

Miami (MIA) – Cuba on American Airlines 

Details — Miami is one of the biggest gateways for Cuba-bound Americans. AA has chartered flights to cities including Havana, Santa Clara, Holguín and more.

Tampa (TPA) – Cuba on American Airlines 

Details — Like Miami and other cities in Florida, Tampa is a big origin for Cuban travel. Most of Tampa’s flights on AA are seem to be bound for Havana, although a few fly elsewhere.

JetBlue has flights to Cuba from three cities in the US. Image courtesy of Shutterstock.

JetBlue Airways, like American, has a strong presence on flights to Cuba, specifically from its East Coast focus cities. In fact, the airlines share charter companies ABCCuba Travel Services and Xael Charters Inc. However, while AA recently expanded to the West Coast, JetBlue only offers flights from Florida and New York. Additionally, JetBlue advertises its usual experience, complete with free snacks and drinks and DirecTV.

New York (JFK) – Havana (HAV) on JetBlue

Details — JetBlue’s JFK-HAV service was one of the first announced after the easing of restrictions and was one of the first to depart from New York.

Fort Lauderdale (FLL) – Havana (HAV) on JetBlue

Details — While American is the biggest carrier operating flights to Cuba in Miami, JetBlue launched its charter service in nearby Fort Lauderdale.

Tampa (TPA) – Havana (HAV) and Santa Clara (SNU) on JetBlue

Details — Tampa is JetBlue’s only US origin with two destinations in Cuba.

TPG flew Sub Country on his flight to Cuba.
TPG flew in a Sun Country aircraft Cuba Travel Services on his flight to Cuba.

In addition to the major airlines operating flights to Cuba, a number of companies also operate charters independently. Here are alternatives if you’d prefer to book directly with a charter service:

Airline Brokers Co.

Fort Lauderdale (FLL) — Havana (HAV) — operates weekly

Miami (MIA) – Havana (HAV) — operates daily

Tampa (TPA) — Havana (HAV) — operates weekly

Airline Brokers Co. also has less frequent flights to:

  • Camagüey
  • Cienfuegos
  • Holguín
  • Manzanillo
  • Santa Clara
  • Santiago de Cuba

Choice Aire (operated by Swift Air)

Fort Myers (RSW) — Havana (HAV) — operates Friday and Mondays

Miami (MIA) — Havana (HAV) — operates every day except Tuesday and Saturday

Gulfstream Air Charters (Operated Aruba Airlines)

Miami (MIA) — multiple destinations in Cuba — operates daily

HavanaAir (operated by Eastern Air Lines and Air Key West)

Miami (MIA) — multiple destinations in Cuba — operates daily

Key West (EYW) — Havana (HAV) — operates Monday, Wednesday and Friday

Island Travel and Tours (operated by Swift Air)

Fort Myers (RSW) — Havana (HAV) — operates every day except Tuesday

Miami (MIA) — Havana (HAV) — no published scheduled

Orlando (MCO) — Havana (HAV) — operates Wednesday and Sundays

TPG flying to Cuba.
TPG flying to Cuba.

Final Thoughts

In spite of the barriers and difficulties associated with Cuban travel, a trip is still very much possible for American travelers. If you’re not interested in flying through a third country like Canada or Mexico, a charter might be the best option — especially if you’re based in a city with charter flights. Ultimately, however, this trip is going to take a bit more planning and cost more than other similar trips you might take to the Caribbean or Latin America. But for many travelers, the unique Cuban experience is well worth the trouble.

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