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How to Book a Flight to Cuba

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I took my first trip to Cuba in January, immediately after President Obama announced an easing of prior travel restrictions. There was a lot of confusion that day — charter companies didn’t know how to respond to the new rules, and most of them were sold out anyway, so I decided to travel via Grand Cayman. The extra travel time added by the layover wasn’t ideal, but I got there (and had an amazing time), and that was what mattered.

There were (and still are) many challenges to visiting Cuba, like no easy way to book flights online, and no ATM withdrawals or US credit card use on the island (MasterCard and Amex are in the process of setting up shop there, so that should be less of a concern moving forward). However, it’s now clear that the US government is no longer very invested in keeping Americans off the island, and has essentially opened up travel for almost everyone.

Technically pure tourist visits aren’t approved, but there are 12 very broad categories that allow you to basically approve yourself for a trip — meaning you don’t need to apply for a license from the Office of Foreign Assets Control (OFAC). With fewer hoops to jump through, I decided to again look into booking a seat on a direct charter flight for my second visit.

There are a number of charter options for reaching Cuba from the US.

I enlisted the help of expert Cuban luxury travel agent Johnny Considine from Esencia Experiences, who was instrumental in helping me book a charter flight from Miami to Santa Clara (so I could explore Trinidad), with a return trip from Havana to New York (JFK). It was only $65 to upgrade to first class, so I figured why not splurge!

I booked my flight with a company called AC Journeys (more formally, Anthropologie Consulting, LLC). My contact there (company president Jose Pineda) sent me flight options to choose from, and I simply gave my approval for the one that worked best. I then had to send in a scanned copy of my passport along with a signed reservation form to affirm that my visit to Cuba is for journalistic purposes.

In total, I paid $1,014 for my flights in first class (more on that experience later). That’s not cheap, but considering it was actually less than what I paid to fly by way of Grand Cayman last time, I was content. The one thing I wasn’t content with was the request to arrive a full four hours prior to the flight. I managed to negotiate that down to a little over three hours (for my first flight), but it’s still a lot earlier than I would get to the airport for just about any other flight. Add that to the list of reasons I’ll be celebrating when the Miami Centurion Lounge finally opens.

I can’t emphasize enough how much easier it was having an agent to book everything. While it’s not the cheapest option, it takes the stress out of the trip to have everything prepaid. I definitely recommend both of the services I used, and if you’re looking for a high-end Cuba experience, you should feel free to email John Considine at Esencia Experiences or Jose Pineda at AC Journeys for assistance. Tell them I sent you, and they may be able to help you get even better deals and service.

Image courtesy of Shutterstock.
You can fly direct to a number of Cuban destinations, including Santiago de Cuba to see the Castillo de San Pedro de la Roca. Image courtesy of Shutterstock.

If you’re not necessarily looking for luxury or you just need flights, there are plenty of other options. Cuba Travel Services offers flights from New York, Miami, and Tampa to a number of Cuban cities. A. Nash Travel is a full-service Canadian agency that I haven’t used personally, but comes recommended by Lonely Planet and Moon guides to Cuba. There are plenty of others:

  • ABC Charters offers service from Miami or Tampa to Havana, Cienfuegos, Santa Clara, Holguín, Camagüey, and Santiago de Cuba.
  • Vacuba offers service to all of the above, as well as Manzanillo.
  • Marazul offers service to Havana, Camagüey, and Santiago, and Santa Clara.

If you’re determined to plan your own trip, CheapAir is now offering non-stop flights between the US and Cuba that you can book online. You’ll need to certify that your trip complies with one of the 12 categories of authorized travel. You can always apply and get a license, but it seems unnecessary since there are so many cultural/religious reasons why you’d want to visit Cuba, like the famous Cuban Art Biennale coming up in May.

I’m excited that Cuba is becoming more accessible, and I think it’s a great time to go. I’ll be posting more about my experiences on this trip in the coming weeks, and I look forward to hearing from those of you who have had the chance to visit, or who are planning to travel there soon. For more on what to do and where to stay in Havana, check out these posts:

What To Do and See in Havana, Cuba
Hotel Review: Hotel Occidental Miramar in Havana, Cuba
Where and How to Book Hotels in Havana, Cuba

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