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48 Hours in Havana

Updated: Feb 20, 2020


There’s just something about Havana. 90 miles south of the Florida Keys,

the enigmatic Republic of Cuba has long been a forbidden fruit for Americans. Bearing decades of contention and embargoes between us vs. them, what do we really know about the sovereign state? You know, besides the cigars and rum, Che and Desi? Does Cuba live up to the hype, or is it just another Caribbean isle with the added allure of political naughtiness? Call me Eve, but I wanted a bite.

Since the establishment of open lines for communication by the late Obama era, the subject matter of American tourism in Cuba has read like an old flame never truly left behind; two steps forward, one step back- it’s hot, it’s cold, it’s… complicated. With all the clutter surrounding the circumstances that warrant travel to Cuba, the latest restrictions put into place by our current administration, and what charters can go where, it’s enough to make one’s head spin. Yet still, you might as well chant “¡Viva la Cuba!” because the particulars are surprisingly stable and effortless, and getting there is only as complicated as one makes it. With the aforementioned in mind, as I was about to commence my Cubano rendezvous, two probing questions stood to be addressed; is Cuba really worth all the fuss, and does a destination wedding hold a place there? Spoiler alert: the all-encompassing TL;DR verdict is in, and it’s a resounding hell yes.

Havana had 48 hours to win my heart, and it wasn’t without its hurdles to do so. For starters, I’d need a tourist visa and itinerary that conformed to one of eleven approved categories of travel, as set forth by regulations within the Office of Foreign Asset Control. Then, once on the ground, my American credit and debit cards would be non-operational; in Cuba, I am only as rich as the cash I have on hand. From there, for reasons above my comprehension, a vast number of luxury hotels appear on the United States’ restricted list. Even Wi-Fi wouldn’t come by easily, and it would be audacious to roll the dice and enable cellular data roaming in Cuba, unless I was feeling keen on some post-travel sticker shock. Silly me, I went in a bit of a Negative Nancy, but it turns out I was just a Foolhardy Fanny. So how exactly did an island 780 miles long ultimately command my adoration? Smoke and mirrors? I think not. Oh Havana, how do I love thee. Let me count the ways.


Enter Cultural Cuba, which for descriptive labeling purposes is a destination management company geared specifically to customized luxury (and legal) travel to Cuba, but I find this categorization to be mildly misleading. If Superman were truly just another fella sporting hipster frames, doing his nine-to-five in Metropolis, then I suppose you could call Cultural Cuba a [yawn] “destination management company”. I like to think of them as more like that friend of a friend who knows all the right people and places. Someone to name drop; someone with the kind of connections that money can’t buy. Having Cultural Cuba at your side isn’t just an amenity. I’d argue to say that when it comes to navigating the edifying archipelago, the Florida-based company is downright essential to the experience. As for weddings, they moonlight there too at the top of their game, in a way that no destination wedding planner could possibly rival. Just ask Usher, whose wedding Cultural Cuba had seamlessly planned and orchestrated with just 48 hours notice.