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Historic First U.S. Flight to Havana: My Unforgettable Trip to Cuba During Castro's Passing

Bleary-eyed from an early wake-up, I arrived at the departure gate ahead of my 7:30 a.m. Monday flight to Cuba, eager for the historic events ahead. As the first direct U.S. commercial flight to Havana in over 50 years, the excitement was palpable—rumors of free snacks proved true.

After savoring a croqueta de jamón, boarding commenced. In celebration, passengers received Cuban hats, certificates, and U.S./Cuba flag pins as souvenirs.

The trip gained even greater significance that weekend: Fidel Castro had passed away. While Miami's Little Havana celebrated, Havana observed nine days of mourning with a music ban—and rumors of an alcohol ban. I was determined to enjoy a mojito before leaving. Castro's ashes were on display upon arrival, drawing global attention. Even before takeoff from Miami, NBC's Lester Holt sat beside me, set to broadcast NBC Nightly News from Havana. After skirting the Florida Keys and a brief southward turn, we touched down in Havana.

As a seasoned traveler to over 70 countries, Cuba stands out as uniquely captivating. Millennials take note: reliable cellphone data is scarce and costly; Wi-Fi requires $4 one-hour scratch-off cards from government hotspots, identifiable by clusters of phone-glued locals.

In this socialist nation, the government controls key supplies, impacting tourist restaurants. Black markets help, but demand from a 4,000-passenger cruise ship can deplete menus quickly. One spot I visited was already missing half its options upon my arrival—I ordered swiftly.

Havana essentials include staying in a casa particular—privately rented rooms or apartments offering authentic immersion and local insights, bypassing government hotels. Since March 2016, Airbnb simplifies bookings. Opt for residential Vedado or vibrant Havana Vieja to directly support Cubans.

Historic First U.S. Flight to Havana: My Unforgettable Trip to Cuba During Castro s Passing

Photo from Flickr by Joe Ross

Don't miss Fusterlandia, artist José Fuster's mosaic-transformed neighborhood on Havana's outskirts. His free-to-visit home gallery funds community projects.

Among my fondest memories: navigating Old Havana on foot with a paper map, wandering streets rich with centuries-old tales. Havana felt remarkably safe for solo miles-long strolls.

Note: U.S. tourists must select one of 12 travel categories (broadly defined; I was never questioned). Exchange euros, not USD, to dodge the 10% airport tax—options like euros, Mexican pesos, or Canadian dollars work.

Havana's charm, quirks, and welcoming people make it a must-visit. With changes likely ahead, book soon for this evolving destination.

Mark Jackson is a blogger and deal finder at BradsDeals.com, with travel experience in 70+ countries.

Lead photo by Lena Wurm / Shutterstock, Inc.

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