
48 Hours in Havana

Lost in a Cuban dream...
There are very few countries I’ve visited where upon arrival I’m instantly absorbed in its sense of place; where the grandeur of its atmosphere matches the destination. Ever-alluring for its suave timeliness, Cuba is one of these places; it consumed me immediately. Sure, the obvious place-marks of vintage cars passing by on the highway and Spanish baroque homes lining downtown Havana visually transported me to the 1950s, it was ultimately the aura of Havana and its locals that influenced this time travel; far more profound than expected.
This aura kept me running on fumes all weekend as I experienced a slice of what Havana has to offer over 48 hours. For the old-world curious, this island—the largest in the Caribbean—can’t be missed. So what’s the best way to ensure you do it right?

First things first— with the impending travel restrictions due to US-Cuba political relations (I promise I’m not going to comment on politics) there are now very few ways to travel to Cuba legally and safely; with that said, I can’t imagine experiencing Havana any other way than with the tour company I traveled with, Cultural Cuba, under the regulation of ‘traveling to support the Cuban people.’
Cultural Cuba offers completely customizable itineraries and ensures genuine interactions with a variety of locals—ranging from artists and fashion designers to musicians and volunteers at non-profits. Though my itinerary was steeped in the specific culture of creative entrepreneurship emerging throughout Havana, I think any non-creative would find this itinerary fascinating. Thus, I wouldn’t write this style of trip off; Havana’s talent is about so much more than art, music, food or dance, it’s about a brimming hope in the youth ready to inspire a new generation.




HIGHLIGHTS:
Visiting + shopping at Dador — coming from a western city, you’d think shopping at a boutique is no big deal, but, Dador is one-of-a-kind in Havana. Established by three young women just 11 months ago, this is a fashion-artist boutique that blends contemporary-Cubano style, with options to custom-order complete outfits, and art pieces that portray an eclectic feminine spirit.
Indulging in mojitos — whether you’re learning the ratio of rum to soda water and mint at a hole-in-the-wall bar, or popping into Ernest Hemingway’s favorite watering hole, El Floridita, the mojito is a must-drink; after all it was invented here.
Smoking a cigar — prior to this trip, I’d probably taken two puffs of cigars; on this trip, I smoked two cigars in one day. That might sound aggressive, but it’s just the lifestyle, everyone smokes. Cultural Cuba will ensure you learn how to cut, light and properly puff a top branded cigar during your trip; perhaps even in a private tasting room, accompanied with its counterpart, rum.
Though I wasn’t able to partake in these options, Cultural Cuba offers highlight activities such as salsa dancing, cooking classes, visiting Ernest Hemingway’s estate 30 minutes outside of Havana, visiting the fishing village of Jaimanitas, touring the historic Hotel Nacional or touring a cigar factory.
EAT:
La Guarida — settled in one of Havana’s famed edifices—known for its appearance in "Strawberry and Chocolate," the only Cuban film to be nominated for an Oscar to this day—La Guarida is a must for sampling Cuban cuisine with a twist; marlin tacos, lamb ropa vieja, suckling pig and octopus carpaccio are a few menu favorites.
5 Sentidos — as one of Havana’s newest restaurants—emerging with the culinary revolution in the past five years— 5 Sentidos is true to its name ('five senses'), allowing diners to experience reinvented Cuban cuisine. Order pork belly with passion fruit sauce, arancini stuffed with rope vieja, fish stew, and lobster ceviche then wash it all down with a guava mojito… or two.
As briefly mentioned, within the past five years, Havana’s culinary scene has transformed. My guide explained how the typical ‘rice and beans’ evolved to reflect a new wave of innovative chefs, working to place Cuba on the culinary map. When it comes to desserts at either restaurant, keep an eye out for guava and cream cheese, anything lemon, as well as any variety of fried dough.
DRESS:
There is no dress code for women, though I’d recommend packing light flowy pants, skirts or dresses to keep cool throughout the day which also transition into evening wear. There is, however, an expectation for men to wear pants come night fall. It’s acceptable to wear shorts throughout the day, but be warned, come cocktails and dinner, don’t forget to change into pants as some restaurants and venues can refuse entry if men aren’t adhering to their pants dress code.
Lastly, I visited in early November and was struck by how few tourists were around. I came to find out November is still considered off-season, thus, quieter streets, and a more authentic, immersive trip. Peak season ranges from December to April.

Although it may be hectic, I hope this shows that you can do Havana in a weekend or long weekend. If you have any logistical questions, feel free to shoot me an email or even, start planning your itinerary with Cultural Cuba!
Xo,
J