Cuba is romantically characterized as a land of intrigue and glamour for good reason. Just 90 miles off the coast of Florida sits a nation that served as a Cold War chess piece in the 40-year match against the USSR and USA, a nation that remains one of the few communist experiments still under cultivation—or perhaps more aptly stagnation, and a nation that encapsulates the allure of classic cars, sumptuous mojitos, and a destination frozen in time.
Truth is, it was never all that difficult to get to Cuba. Americans have been going for decades – by the tens of thousands per year via Canada, Mexico, the Caribbean, or Central America.
Now it is even easier – you can even use your frequent flyer miles to get there.
Cuba was on my travel wishlist since I was in high school – perhaps even going back to childhood when I would hear Ricky always talking about Cuba on I Love Lucy. The opportunity finally arose thanks to a Christmas raffle while I was working for Star Alliance. The prize was an economy class ticket on Avianca-TACA to any destination served. That opened up a lot of possibilities – Madrd perhaps? Buenos Aires? Santiago?
Then it hit me. Havana. Done.
Booking required a bit of acrobatics on the part of TACA – since I was originating the United States, two tickets had to be issued, one round-trip from Los Angeles to San Jose, Costa Rica and the second ticket between San Jose and Havana. This is no longer an issue.
Tickets issued, I contacted an Award Expert client in Florida who has become a friend over the years and travels frequently to Cuba. He put me in touch with his contact person in Havana, who set up a driver to meet me at Jose Marti International Airport in Havana.
I booked a room in family home (Casa particular) in Havana online using hostelworld. The cost was only $9/night. It is little surprise that Cuba does not have any American hotel chains (yet), but the hotels that are available are very pricey yet lacking in luxury and amenities. That is part of the charm, no doubt, but I saw no reason to spend $250 on a hotel when I could get a more authentic experience staying in a spare bedroom of a family.
The purpose of the trip was to explore further the Cuban Aviation Industry. Cubana always fascinated me and I was determined to get on an aging Russian aircraft while I was there. Stay tuned for the adventure that turned out to be.
Cuba fit the cliché in so many ways, yet I was thrown several curve balls that permanently altered the way I viewed the nation. This report will recount my time in Cuba and showcase the paradoxical charm and loathsomeness of this enigmatic place.
Read more of my Cuba trip report:
Planning a Trip to Cuba
Los Angeles to Havana in TACA Economy Class
Visa Requirements for Visiting Cuba
Day One in Cuba: A Tour of Havana
Day One in Cuba: An Evening Surprise
Day Two in Cuba: Accused of Being An American Spy!
Day Two in Cuba: Escorted Flying
Day Two in Cuba: The Juxtaposition of Two Cubans
Havana to Los Angeles in TACA Economy Class
10 Tips for Visiting Cuba
Why You Should Visit Cuba Now