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Cuba Libre

Traveling To Havana Cuba

So, you’ve finally decided to see what this magical and supposedly forbidden tropical island is all about. Interestingly, you’ve decided to look past the smoke screen that is 60+ years of anti-Cuba American foriegn policy. Fact is, as Americans, we’re allowed to travel just about anywhere we’d like, it’s just that elements of our federal government want you to believe otherwise.

Wanna know what to expect in Cuba? Sure, most people love a good adventure, but a little bit of intel can go a long way to a lot more fun and more efficient use of your time.

Key West To Havana

What makes Cuba so special? For openers, each and every person who has been there will tell you it’s the people, the lack of fast food joints and maybe, just a little bit of the ‘forbidden fruit factor.’

Traveling from Key West, there is limited availability to book a Havana Excursion through OurKeyWest, otherwise, you can fly through Miami, which I do most of the time. You’ll know you’re close to the check-in lines when loud, hurried Spanish is the dominant language, and huge duffel bags wrapped in multiple layers of blue cellophane dot the landscape.

Among the crowd are gringos, Latin hoochie mamas with five-inch heels, a religious group or two and the apprehensive elderly, those that have rarely, if ever, been on an airplane. Thankfully, the flight is so quick that once the plane reaches altitude, it’s time to descend. 

Billowy clouds often gather over the green-blue water-edged land mass that gives way to the bright, red Cuban soil. Huge tracts of farmland slowly transition to block-style, cement, Russian-built apartment complexes and finally, the runway at Jose Marti International Airport comes into view. Much more often than not, the touchdown is immediately followed by a round of applause from the passengers. Really? Is it that much of an accomplishment to land this plane? This is just the beginning of things on the ‘never seen anything like that before’ list.

Traveling to Havana Cuba

Nearing the gate, no one really respects the pilot’s plea to stay seated as the next chapter is the mad dash to customs. If you’re lucky, you’ll que up quickly and get a friendly agent. Not surprisingly, they’re not the cheeriest group of folks you’ll meet, but after comparing your face to your passport and a quick mugshot, you’re on your way to an antiquated x-ray machine–that’s right, in Cuba they x-ray your belongings after you land. Now the luggage waiting game begins, and the next step is either a breeze or a drag, depending on what you’ve brought. Chances are, if you’ve been before, then you will have all manner of ‘stuff’ you’ve brought as gifts of essential items for the incredible Cuban people from past trips. This could be anything from AA batteries, to baby clothes, to jump drives, to parmesan cheese. The question is, does the next agent want to take a peek? If you’re lucky enough to get the ‘go ahead’ nod, take a look to the left and witness the unlucky bastard whose bags are being disemboweled and scrutinized, a process that can quickly eat into the better part of your day. 

Whatever you do, don’t stare, just keep walking.

Once the automatic doors open to the outside world, don’t be surprised by the sea of disappointed faces glued to the security fence. It’s nothing personal, it’s just the friends and family members trying desperately to catch that first glimpse of their loved ones, many of whom they’ve not seen in ages due to financial reasons and outdated U.S. laws. Out front, taxis of all sizes, shapes and ages line the sidewalk. Everyone within sight is either smoking filterless cigarettes, cramming croquettes into their mouths or chugging down buccis or beers, not to mention the occasional flatscreen TVs being gingerly loaded into an ancient vehicle. Just beyond the parking lot are the first of many pro-government signs with images of Cienfuegos, Marti, Castro and Guevara. You’ve made it, and it invariably feels like much more than 90 miles from the United States. I’d say something closer to Africa. And yes, it’s beyond cliche, but between the 1950s vintage cars–somehow still chugging along–and the wide smiles and warm and welcoming attitude of the Cuban people, it feels like a bygone era.

Havana Cuba Travel

Driving the ten or so miles from the Airport into Old Havana, the out-of-the-ordinary quickly unfolds. Look to the right, and there’s a guy with two turkeys slung over his shoulder, then a small family of four on a single-seated scooter passes two men with long strands of onions and garlic for sale on the side of a road lined with ordinary Cubans hoping to catch a ride into town to go to work. If they don’t find a ride . . . well, they don’t go to work.  The Cuban people have a saying: the government pretends to pay us, and we pretend to work.

Life is very different in Cuba. I treasure every trip, and I’m sure you will too.

  • By-the-way, if you take the OKW Havana Daytrip you bypass this mess I describe above, flying directly from Key West (45 minutes) and clearing customs at the “private terminal” where your small group is granted VIP processing in less than 15 minutes. Trust me, it’s worth the extra $100.
Rob O'Neal
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