This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.
Update: Some offers mentioned below are no longer available. View the current offers here.
The first time I went to Cuba, I booked a last-minute hotel from A. Nash Travel, flying via Grand Cayman and buying a $20 tourist visa there. My second time around, I enlisted the help of Cuba-based luxury travel agent Johnny Considine from Esencia Experiences, Miami-based Jose Pineda of Anthropologie Consulting Journeys and Miami-based travel agency Cuba Travel Services, who all played a role in booking my Sun Country charter flights to Cuba.
TPG Photo Editor Julio Gaggia and I flew two of these charters—one from Miami (MIA) to Santa Clara (SNU), and another from Havana (HAV) to New York (JFK)—and while we didn’t find much in the way of creature comforts, we did love the luxury of flying nonstop from the United States.
The collective base fare for each itinerary cost $699 per person, but I also purchased first-class upgrades for each flight—$65 per person for MIA-SNU and $250 per person for HAV-JFK—bringing the total to $1,014 per person. Knowing we’d be waiting about a half-hour on the ground before each take-off, I figured that these low upgrade costs were worth being comfortable on our relatively short flights. I paid with my Chase Sapphire Preferred to earn 2x on general travel expenses, even when charged through a travel agent.
I wanted to earn some points for the flight as well, but no dice. Cuba Travel Services’ poorly managed rewards program is supposed to give you points every time you fly charter flights, employing an app called Spot On to help you track your account, but when I downloaded the app and tried signing up for the program, I encountered a “no funciona” error—I’ve since reached out to Cuba Travel Services to voice my frustration.
Miami (MIA) to Santa Clara (SNU)
At Miami International Airport (MIA)
We were told to meet Jose Pineda in the lobby of Terminal E four hours before our 1:45pm flight, but I pushed back because I thought this was ridiculous—we weren’t even checking bags. Jose then agreed to let us meet only three hours early, but even this was totally unnecessary. Check-in and security at MIA were both a breeze, so we had lots of time on our hands before we finally took off.
Sun Country flights don’t come with any lounge access, but there’s a Priority Pass Lounge at MIA’s Concourse F called Club America—a place so basic that they don’t even give you bottled water. You and a guest can get access to this lounge with the Priority Pass Select benefit from your Citi Prestige, but if you’re traveling with a companion using the Priority Pass Select benefit from your Platinum Card, The Business Platinum Card from American Express OPEN , or Mercedes-Benz Platinum cards or your Priority Pass membership, I wouldn’t spring for the $27 guest fee—I don’t think it’s worth it for the cookies and fountain soda.
On Board MIA-SNU
Boarding the 737-800 went smoothly, and by the time they closed the door only two of the 12 first class seats were filled…by us. Arranged in a 2 x 2 configuration, these blue-leather-upholstered recliner seats with 37-39 inches of pitch and 21 inches of width were certainly comfy—and looking back at the packed-to-the-gills coach cabin of 150 seats, I felt even better about spending that extra $65 per seat for first-class upgrades.
The very friendly cabin crew was Miami-based, and made us feel very at home while we enjoyed a leisurely drink during our one-hour flight.
At Abel Santamaría Airport (SNU)
Interesting fact: After going through immigration in Cuba you need to go through a metal detector again, I assume so they can see if you’re bringing in any banned electronic equipment—like walkie talkies.
Our Cuban tourist visas were prepaid by our agents so immigration was a breeze—we simply said we were in Cuba as tourists, and it worked like a charm. However, I’d recommend having all itinerary/plans printed ahead of time, because you won’t have cell access to bring up emails if you’re questioned on your trip. This is actually a good rule of thumb to follow in any international country; I’ve been interrogated the most in Canada and the UK.
There’s not much in the way of passenger services at SNU, but we easily found the helpful Cuba Travel Services desk where we picked up our travel vouchers and affidavits for our return to the US (more on these later).
Havana (HAV) to New York (JFK)
At José MartÍ International Airport (HAV)
On my first trip to Cuba, I had access to Cayman Airways’ “super exclusive” VIP Lounge at Havana’s airport, but with Sun Country we once again had no lounge access. Unfortunately, HAV doesn’t have much in the way of food, so you’ll want to eat before you go.
You’ll also want to arrive at the airport early, even if you’re flying first class, as there’s no first-class check-in lane, just a bunch of check-in agents for various charter flights. We waited in a check-in line for about 20 minutes, but at least security wasn’t that bad.
On Board HAV-JFK
Our flight aboard this second 737-800, with the same first-class config and seats, was blissfully uneventful. We were, however, served a simple meal of a chicken salad with dried cherries, as well as a rustic roll, crackers and cheese and a piece of cake. Nothing fancy, but it was tasty and relatively healthy. (There’s protein in cake, right?)
Our flight was 4 1/2 hours long and had no WiFi, so in case you didn’t pack your own entertainment, it’s good to know that for flights over three hours, Sun Country provides handheld DigEPlayers with 7-inch screens, based on availability. Pre-programmed with movies, games and music, these are complimentary for first-class passengers, and cost $8 in coach (or $12 for those traveling from Minneapolis-St. Paul).
At John F. Kennedy International Airport (JFK)
The affidavits we’d picked up in Santa Clara were forms explaining the reason for our trip, and were meant to be presented to anyone in authority who might have asked us why we went—though no one ever did. Returning to New York JFK, I went through Global Entry with no issues at all; apparently, no one cared that I’d just been to Cuba. (I hope you feel differently when I share more trip reports next week!)
This wasn’t what I’d call a glamorous experience, but I definitely enjoyed being able to upgrade so cheaply to first class and fly into a smaller Cuban airport like Santa Clara. Sun Country flies from MIA, JFK and Tampa (TPA) to Havana, and also flies from MIA to Cienfuegos (CFG), Holguin (HOG), Santiago (SCU) and Camaguay (CMW), as well as Santa Clara (SNU). Other charters available through Cuba Travel service are offered by American Airlines, and starting July 3, once-weekly JetBlue flights from JFK to HAV will be offered via the agency, as well.
The true luxury was in having nonstop flights that didn’t require connections in other countries, as is the case with carriers like LAN, Copa and Virgin Atlantic. On Cayman Airways, for instance, I had to fly from MIA to HAV through Grand Cayman—and though it’s not that far from Miami or Havana, it added hours to what should have been a very short trip.
Happily, JetBlue has just announced that beginning July 3, it will begin flying nonstop from JFK to HAV once a week, making it another nonstop option that can be booked through Cuba Travel Services. To learn more about making flight arrangements through travel agents or booking your own charter flights though an online travel agency like CheapAir, be sure to see my recent post on How to Book a Flight to Cuba.
And rest assured, you’ll love visiting this beautiful island country. NEW INCREASED OFFER: 60,000 Points TPG'S BONUS VALUATION*: $1,200 CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners *Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.
NEW INCREASED OFFER: 60,000 Points
TPG'S BONUS VALUATION*: $1,200
CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners
*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.
Know before you go.
News and deals straight to your inbox every day.