I didn’t realize that we’d be flying over Cuba on Southwest on the way to and from our Jamaica All Inclusive Resorts in Montego Bay. So it was a little surreal to actually fly over this communist country that I only knew of through history books and watching the news.
The thing that really struck me was that, from the air, it just looked like an absolute tropical paradise.
How is it possible that a beautiful island with similar natural resources to its many neighbors could be in such economic and political turmoil?
I don’t have the answers but I do have some pictures that are just spectacular.


This was one of our many, many free trips on Southwest Airlines thanks to the Southwest Companion Pass. While the Companion Pass is the best deal in loyalty programs right now, some of the recent Southwest changes have us concerned about the future of the airline.

Williams Island, The Bahamas
As a bonus on this flight, we were able to get a great view of the Bahamas. Williams Island was clearly visible off the tip of North Andros.

While we’ve not visited Cuba yet, this view of the Bahamas reminded us of our budget trip to Grand Hyatt Baha Mar in Nassau.
Flying over Cuba on the way to Jamaica
We’ve now had 2 trips to Jamaica to stay at 3 different All Inclusive resorts in Montego Bay. On both trips, we flew over Cuba on the flights to & from Montego Bay Airport.
Our stays were at:
- Hyatt Zilara Rose Hall
- Secrets St James
- Zoetry Montego Bay
We had a great time in Jamaica at these resorts. But our brief trips though Cuban airspace was an experience that I will not soon forget.
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