Traveling to Cuba Legally In My Lifetime

Interesting old building in Cuba. Photo courtesy of

For years I have dreamed of traveling to Cuba. My desire may have originated with the movie Havana, which starred Robert Redford, but since then I have become even more intrigued upon seeing photos of streets filled with 1950’s and 1960’s era cars and hearing stories of the wonderful music that emanates from bars and cafes on every street.

I have seriously considered entering Cuba via Mexico, the Bahamas, or Canada, as Americans have been doing for years, but just never pulled that together. Three years ago, I even booked a tour through a firm that had obtained legal permission to travel to Cuba under the auspices of a “cultural exchange program” but then had to cancel that trip for personal reasons. So when I read that the rules regarding Cuba travel had been eased, I was excited.

Previously, rules imposed by the Treasury Department only allowed Cuban-American to travel to Cuba once every three years to visit qualifying relatives and to spend no more than $50 a day. The definition of a relative was narrow – including only parents, spouses, or siblings. The bill that President Obama signed into law now permits Cuban-Americans to travel to Cuba to visit close relatives for an unlimited period of time once every 12 months and to engage in travel-related transactions at the maximum per diem rate in effect at the time of travel, which is currently set at $179 per day.

Since I am not of Cuban descent, traveling to Cuba legally is not yet a possibility for me, however I have hopes that the travel ban will soon be completely lifted.. Havana will likely never again be the hotspot of gambling, nightclubs, and hedonistic lifestyle that it once was, but the beaches are still exquisite, the hotels full of old-world charm, and the music as vibrant as ever. While I may be harboring a romanticized picture of the country, I’d sure like the opportunity to find out in person. I, for one, am really looking forward to the day when all travel restrictions will be lifted.

Typical old car on the streets of Cuba. Photo courtesy of

5 thoughts on “Traveling to Cuba Legally In My Lifetime”

  1. I’ve been thinking a lot about Cuba, too. 🙂 Would love to one day visit, especially whichever shore gets the best seashells rolling in 😉


  2. It seems so inconsistent. Surely there are despicable nations on the planet that might warrant such a law, but I struggle to believe that Cuba is one of them.

  3. In my youth I was so puzzled by Guys and Dolls, where they take an evening trip to Havana…

    When I was a teenager the first airline hijackings were good natured jaunts to Cuba and I imagined being lucky enough to be among them.

    Time now for change, I think. Not Guys and Dolls, not hijackings, but grown up converse amongst neighbours.


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