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48 Hours in Havana

Updated: Feb 20


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.

A quick direct flight from New York’s John F. Kennedy International Airport, the actual getting to Cuba part was a cinch. I’d made zero effort up to this point, as my visa and particulars had already been arranged on my behalf by Cultural Cuba. I was set to go under the “Support for the Cuban People” category of approved travel, and if it sounds like I was headed into an itinerary packed with tiresome goodwill checkpoints, I’d advise you guess again. A broad category which essentially decrees that a traveler must engage in activities that result in meaningful encounters with Cuban civility, culture, and enterprise, independent of its authorities, it is almost as though one is being challenged to relish the experiences that await.


Straight off the plane, I’d joined the group I’d been traveling with to meet the first of many friendly faces we’d come by on the island. Our stellar and affable guide, Alain Rubio, greeted us from the arrivals hall with a beaming smile and hearty welcome. He is one of 17 individuals that make up Cultural Cuba’s staff on the ground in Havana. Alain is a walking Wiki for everything that pertains to the region, and all of which he speaks is wholly fascinating. Curiously, for someone who had only learned to speak English during his years in university, his diction and inflection is so clear and familiar sounding, I’d have gambled he hailed from New York, and lost dearly.

Our first stop was a brief but worthwhile one, as we’d made our way to the Head Start Pre-School for Disadvantaged Students, a small school run by convent nuns for children aged 2-5 coming from challenging home environments. This item on the day’s program is just one of the many optional offerings afforded by Cultural Cuba, whose custom crafted itineraries are suited to meet the interests and desires of its clientele. While it may not top the list of priority encounters for all vacation goers, I’d found the experience of engaging with the school’s sweet-as-pie children and dedicated administration to be one that is food for the soul. My group had come set with trinket donations of crayons and more, for which the establishment hosting us was supremely grateful.


Afterward, we’d headed to San Juan Bar & Grill, a popular eatery in Old Havana where tourists are noticeably absent. A gem by local standards, it’s one of the many places Cultural Cuba has sourced as the anti-cookie cutter place to be. Joined by the company’s owner and founder, David Lee, we’d eagerly kicked off a weekend to remember. A sumptuous spread of authentic Cuban fare lined the table, but not before each of us got behind the bar for a cocktail mixology lesson. Personally, I’d gone for the extra long pour, and the outcome was delightful.

It wasn’t long before I’d begun to take notice of the unusually special highlights Cultural Cuba has to offer. Around the time we were invited to peruse Amos, a photography studio run by Alex Castro (the son of Fidel Castro) and Ramses Batista (of no relation to Fulgencio Batista), and chat intimately with the pair, I’d realized that the experience laid before me was not your run-of-the-mill visit to Cuba. Mr. Lee, whom I suspect would never go by such a formality, is only able to extend such a unique opportunity because of his kinship with the studio’s artistically inclined owners. In lighthearted jest, I’d dubbed David a local celebrity, as he seems to know and be loved by all, but I also recognize that it is not unrelated to the crucial ingredient that makes his company’s secret sauce. When he’d founded Cultural Cuba nine years ago, among the first to do custom, private, and legal travel to the country under Support of the Cuban People, it was built upon a commitment to forging strong ties with the community, and a love for its uniquely vibrant culture. The team’s passion is abundant and translates into immersive one-of-a-kind experiences for its travelers. At the Amos studio, we’d gained keen appreciation for its vast collection of striking photography, and learned of the impact the workshops they provide to local Cuban youth has had on its community.


On to the VIP section of Fabrica de Arte Cubano (or as us English-speaking folk would say, Cuban Art Factory), where we’d enjoyed a divinely eclectic assortment of dishes at Paladar Tierra. Situated in a former oil factory turned multifaceted venue for art, music, cinema, and nightlife, it is the heartbeat of Havana after dark. Composites of contemporary spaces, both intimate and grand, send the locals flocking to the hottest destination in town, where you really get a sense of the accessibility art and talent has here in Havana. A labyrinth of intrigue, it hosts a hipster warehouse atmosphere that seems like something Brooklyn wishes it could pull off. In one nook, a jazz quartet plays tunes that emit smooth and sultry sounds while elsewhere upstairs, a famed local artist stands in proximity of his exhibition. Around the corner, an open-air terrace anchors one of many full-scale bars, as indie films captivate an audience in the gallery beside it. The expansive concert stage complete with a mezzanine would be enough to make the Cuban Art Factory a place of interest, but it’s in the multidisciplinary design that makes it a destination not to be missed. Along one of the perched galleries, a limited edition print had caught my eye, and I was enthralled by the opportunity to own it at a reasonable cost. The kind woman tending to the post offered to have it framed and delivered to my hotel at my convenience, and the jaded New Yorker in me regrettably wondered if I could trust it. I’d then been met with a proper lesson about the Havana honor system, because as we’d discussed payment options, she’d suggested that I pay her via PayPal after I’d returned to the United States with the piece some days later. That’s just the way trust and civility goes down here in this great land.

We’d wrapped up the evening with a stay at La Reserva Vedado, a beautifully renovated historic mansion that reads more like a private palace than a boutique hotel. With just 11 uniquely laid out rooms to accommodate its guests, a casa garden oasis, and a 24-hour bar, La Reserva presents a uniquely decorated option in the Embassy district that is ideal for wedding book-outs. A prepared-to-order breakfast of my choosing on the estate’s outdoor enclosure gets an early day of sightseeing off to its best possible start; I was ready to see and explore the great city which surrounded me.


Upon checking out of La Reserva, we’d headed over to the polar opposite of lodging at Gran Hotel Manzana Kempinski in Old Havana. The towering luxury hotel is as massive as it is primly situated, resting just opposite one of Hemmingway’s famously preferred haunts, El Floridita. Panoramic views of the colorful city are best taken in from the rooftop pool, but one cannot go wrong with some R&R time at the hotel’s rejuvenating spa and handsome cigar lounge. The Kempinski is as luxury as any hotel I’ve ever stayed in, but for reasons unknown to me, it technically falls under the Cuba sanctions restricted list for American tourists. This isn’t to say you’re breaking the law by patronizing the swanky property; while you may not be able to book a suite directly, thanks to a legal loophole that predates the list’s creation, Cultural Cuba squares that away with ease. In a sense, it’s a happy accident too; as a domestically established company, all bookings and payments may be safely processed with Cultural Cuba in the United States ahead of time, avoiding the need for complications, such as carrying a suitcase full of cash into the country in anticipation of settling one’s bill. Bring what you need for souvenirs and incidentals, and never mind the rest. That’s the thing about Cultural Cuba- they take a seemingly complicated scenario and simplify it to no end, and nothing is done without extensive efforts made to ensure that every aspect of the journey exceeds all expectations. If I’ve learned anything from my stay in Havana, it is that one should, however, avoid Airbnb arrangements at all costs. In a city that gloriously blends old and new, it’s a frightful fact that some buildings have structural instability that a bright fresh coat of paint just can’t hold up. Pictures can be deceiving, and it’s best to rely on the wisdom of experts here.

A walking tour of Old Havana introduced endless opportunities to take photographs, from its culturally enriched narrow streets to its wide-open plazas. Boldly colorful vintage cars line the pavement, and it was only a matter of time until I’d been made a bonafide automobile enthusiast. Old Havana embodies fragments of a bygone era, one that I’ve not lived long enough to know, and from my perspective, this secures its spot as one of the most uniquely beautiful places I’ve ever been fortunate enough to witness. Strolling about the town without a care in the world, I’d indulged in fresh churros hot off the oil, and a piña colada cocktail served straight from

the pineapple. For all intents and purposes, I was happy as a clam, basking the vibe of a city that is harmonious and impossibly safe. I wasn’t quite used to such a concept, but I had certainly appreciated it.


Following an extravagant midday spread over at 5 Sentidos, the day’s summit had arrived with a private and exclusive cigar tasting in a secret room at Havana Club Rum, an experience I’d have otherwise never known if not for the Cultural Cuba connection. Hosted by in-house brand ambassador and sommelier Damian Domínguez Pérez, he’d guided us through a consummately Cuban experience that inspired the most fun I’d had in a long time. With his Ricky Martin-esque charm and an accent not unlike Tony Montana in “Scarface”, he’d taken us from cigar and spirit virgins to Cohiba virtuosos in just a couple hours time.

Back to Gran Hotel Manzana Kempinski for a breather and a wardrobe change, we’d enjoyed cocktails and canapés before it was time for yet another exclusive experience. Outside the hotel, two classic convertibles stood by to drive us off into the sunset. Trailing us from another vehicle, Natasha Forcade Goméz, a talented professional photographer under the employ of the Cultural Cuba collective, brilliantly captured us having the time of our lives. With a cool soft breeze fanning my hair against the picturesque backdrop, I was living my best life from the backseat of a turquoise ’55 Buick convertible. Our photo shoot was comfortably casual, and the imagery shared with us less than a day later are just what Instagram dreams are made of.

Our tour with the top down had come to a close as we’d arrived for our dinner reservation at internationally acclaimed restaurant, La Guarida. A dining destination that books out weeks or months in advance, and has hosted countless visiting celebrities, we’d strolled in like it was no big deal, thanks to our hook-up managing the details. Multiple courses of delectable creations had left me feeling quite full, but the night was far from over. A private rooftop mini jazz concert performed by the ridiculously skilled William Trobejo Cuban Jazz Trio left each of us speechless. Its leader, William Trobejo, ignites a feeling of rapture into his compositions, diffusing an eclectic sound that extends far beyond the jazz genre. Left mesmerized by the trio’s mastery and dexterity whose notes let love into my ears, I could clearly envision a magical moonlit wedding reception set to the soundtrack of Cultural Cuba’s not-so-small musical discovery. At the end of it all, it felt only natural to reflect on the experience in good company from the comfort of a leather recliner in the private VIP cigar lounge at La Guardia, with a fine Partagas cigar in one hand, and a stellar aperitif in the other.

The next day, with only a few hours left to explore Cuba before it was time to head home, we’d stopped by a young fashion boutique called Dador, operated by three female entrepreneurs whose artwork and handmade clothing reinvent traditional Cuban design. Sharing with us their story of getting their business off the ground, it was an eye-opening account of the challenges faced by ambitious Cuban youth, yet it is uplifting in its relentless hope and initiative for betterment in the community. In spite of their limited access to supply of textiles due to embargo obstacles, lovingly crafted pieces are created directly in the studio, and many of which have no choice but to be one of a kind. The pioneering ladies of Dador welcome custom commissions with a quick turnaround, and I could see where this offering is a creative natural choice for bridesmaids and more.

One final treat before we’d said our goodbyes where it’s final call for genuine Cuban cigars to bring back home as souvenirs (yes, you may legally bring them back into the United States, within reasonable parameters), we’d visited the Habana Compas Dance (Havana Dance Company), where dance and music becomes one with multicultural influence. An infusion of African, Spanish, and Cuban elements surround the stage, as the troupe made up mostly by women implement unexpected objects as instruments of their art. An outstanding dance company so attuned to one another’s beat and step, they present unparalleled entertainment that would undoubtedly rev up a wedding crowd.

For the likes of little ol’ me, 48 hours in Havana was simply not enough. There is so much more to see and do, from private cigar factory tours to one-on-one salsa dancing lessons, and that’s just specific to Havana. Cultural Cuba’s reach extends beyond the capital city for those with a little more time to spare. For a wedding party, it is best to plan a two to three day getaway, but I’d strongly advise the happy couple to come down ahead of time, going into the celebration with firsthand experience, or hang around for an extended honeymoon. As far as destination weddings go, this is simply the place that no invited guest could possibly decline. Whether exchanging vows on the beach, or dancing the night away in a ballroom, with Cultural Cuba, the sky is the limit, and they know a [totally legit] guy for everything. Cuba is a place where, when someone goes, they come back unable to shut up about it. It opens eyes and expands minds to a beauty previously unknown. Forget the politics. Paradise has been found, and it’s closer than you’d think.

"48 Hours in Havana" is written by Samantha Sendor and appears in the 2020 Edition of Sophisticated Weddings. For more information on custom luxury travel to Cuba, visit Cultural Cuba.

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