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Cuban American flags CubaAround midnight on my last night in Cuba, my travel buddy and I rumbled toward our hotel in a 1951 Chevrolet cab with the driver and his girlfriend, whom we’d become friendly with. Along the Malecón, Havana’s seaside esplanade, we spotted a group of locals hovering around a large fish that someone had caught and hauled onto the sidewalk.

But when we stopped to snap a few photos, it was evident that the sea creature isn’t a fish, but a shark. Exhausted fishermen struggled to hoist the four-foot body of the predator onto a bike taxi to sell at market; a few feet away, teenagers circled around the severed head, touching its fearsome teeth and screaming with skittish delight.


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In a way, that scene – at once chaotic and colorful, raw and wild – helps illustrate a visit itself to this island nation, which has been all but off-limits for U.S. citizens over the past five decades. But, thanks to policy changes passed by the Obama administration earlier this year, the average U.S. citizen can now travel there legally, without the hassle of sneaking through Mexico or Canada, and the fear (and fines) of getting caught.


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I was lucky enough to be among the first groups of American tourists to legally visit Cuba since 2003, when the Bush administration effectively shut it down, and our eight-day trip made headlines in both countries. Our group of 30, who traveled with New York-based operator Insight Cuba, was greeted by television crews both in Miami and in José Martí International Airport in Havana.

a classic car in CubaAs I wrote in a previous post, the new U.S. regulations require that travel must be “person-to-person” through a licensed operator. So it wasn’t much of a surprise that our itinerary, which included five nights in Havana and two in the charming colonial city of Trinidad on the southern coast of the country, was packed with activities designed for interaction with locals. Among them were visits to a maternity ward (which several in our group said felt too invasive), a rural medical clinic, and a community project of Afro-Cuban artists, which I found fascinating because of its connection with the religion of Santería.

Not surprisingly, the unspoken message running through the itinerary was how socialism and former President Fidel Castro’s regime are responsible for the country’s achievements, such as nearly a non-existent illiteracy rate and universal healthcare. And even as hectic as it was, the itinerary provided a good starting point for on-your-own exploring (and gave me a greater appreciation for free time).

Havana Local In CubaIndeed, as is often the case with group trips, some of my most memorable experiences came outside the van and off the schedule: a conversation about living in Spain with an overalls-wearing Havana native over a glass of sugar cane juice; listening to intoxicating Afro-Cuban jazz in an underground bar; being invited into a family’s home in Trinidad, and hearing about their struggles raising a severely disabled daughter.

And, of course, seeing that crazy shark scene unfold on the Malecón.

See my Cuba Libre slideshow for more images from the trip, and check out An American in Cuba (Legally): Part 2, where I discuss specific travel tips for Cuba.

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