Flying to Cuba, The New Way

Flying to Cuba, The New Way

Miami International Airport, 7:30 a.m., Sunday morning. I step up to a kiosk, scan my passport and answer a few questions. A few minutes of work and I have my boarding pass. I step into a short line, and after a brief wait my pass is stamped and I'm sent on my way. Total time spent? Fifteen minutes.

Now that might not seem like a particularly quick check-in process to you, but in my world this was blazing fast. Quicker than quick. Ludicrous speed. For this was no ordinary flight, but my first commercial flight to Cuba from the United States.

I've been going to Cuba since 1996, and I've been there every year since 2010, taking as many as three trips in one year. I've always been able to go legally as a journalist, but my only options from the U.S. used to be charter flights. The flight from Miami to Havana takes all of 46 minutes in the air, but getting in the air via a charter used to take an enormous amount of time, with an arcane and unpredictable series of challenges that wasted hour upon hour.

Allow me to describe how these flights used to work. If my flight was scheduled to depart at noon, I would get to the airport at about 7:30. The first step was to find the counter for the charter, which was never easy. There would typically be a line of people standing in front of their bags, with no one from the airline in sight. I would join the line, and wait. And wait. After 30 minutes (if I was lucky), someone from the airline would show and begin preparing.

At some point—perhaps 8:30—people would move from their bags and line up in a new spot. More waiting. Then I would finally be called to the counter to begin checking my paperwork. This would begin the march through a gauntlet of counters, checking different papers here, paying different fees there, and finally emerging much, much later (perhaps at 10?) with my boarding pass.

I'm certain these flights are the reason for half of my gray hairs.

Journey over? Not quite. After a bite to eat I would move toward the gate and get comfortable. This would be the time to watch a movie as I waited for the arrival of the gate staff. If I was lucky, the flight boarded around noon. If I was a bit unlucky, it would leave an hour late. Some delays stretched far longer, including the time when I was told that there was no crew for the flight.

My longest delay had me spend a solid 12 hours in the airport, and by the time I arrived in Havana it was evening and I was in desperate need of Cuban rum. Not a fun day. I would wind up in Havana feeling like I had been on the losing end of a fistfight. Coming back was more of the same. I would plan a minimum of four hours for connection time in Miami for a flight back to New York and end up spending quite a bit of time at the airport.

Not today. Not any longer. In 2016 the Obama Administration removed the restrictions on commercial flights to Cuba, beginning with provincial cities. In November, the first commercial flight from the U.S. in some 50 years landed in Havana, opening the door to regularly scheduled flights via American Airlines, JetBlue, Delta and a host of other carriers.

Today my flight—American Airlines 1447—took off right on time and landed early. I didn't check a bag (baggage claim can be a nightmare in Cuba) and I was in my hotel in Havana at 11:30 smiling from ear to ear.

As I write this blog, sitting in the Casa del Habano at the Melia Cohiba Hotel, puffing away on a Partagás Serie E No. 2 (our No. 3 cigar of the year) I couldn't be happier. What used to take a day took only a few hours. It's a new day for flying to Cuba.


"Another nightmare you may yet to experience. If your checked bags do not arrive, missed connection or whatever, be aware. I have had items stolen from my delayed bags in HAV twice, even though the bags were locked. I could describe in detail but just let me say that a pointed steak knife can pick the zipper. Yes, the zipper, not the lock. This is at the main international terminal. The customs staff are of absolutely no help. " —March 3, 2017 08:55 AM
"Hi David, as a U.K. passport holder, can I use the flights from USA and am I subject to the questions and procedures as a USA citizen. Keep the Cuban info coming. Thank you" —February 28, 2017 11:26 AM
"Best flight to Cuba: Private charter out of Lauderdale to negotiate originating the Today show from Havana. Best flight from Cuba: The private GE jet to Miami and then to NY. " —February 27, 2017 17:56 PM
"After being on two of those Charters with you, 2012 & 2014, we went there in December on Southwest from Tampa. Great article because you perfectly described our feelings. Wish you would've written it before we went because we checked luggage and waited over two hours for it to come up. Going later this week and will definitely only use carry on. BTW, I'd avoid Miami at all costs. " —February 27, 2017 16:51 PM
"I'm flying back on that Delta flight myself so I hope I have the same type of trip as you. Thanks for reading and thanks for the comment. " —February 27, 2017 16:13 PM
"David I just got back from Cuba via JFK straight to Havana on Delta. The entire process couldn't have been better. When I returned to NYC it was the quickest trip through customs ever. I was very pleased with the ease of travel. Looking forward to heading back! " —February 27, 2017 16:07 PM
"Yes, I jammed a heroic amount of clothing into my carryon, which threatened to burst at the seams. I nearly threw out my back hoisting it into the carry on bin. All good in the end. " —February 27, 2017 15:33 PM
"Hello! If you didn't check any clothes, all packed up smartly in your carry on? Enjoy your Festival my friend! Wish I'm there next year. IG: @cigars4soul" —February 27, 2017 14:49 PM