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Cuba’s Timeless Charm: A Journey for Expats Looking Beyond the Usual

There are more than a few ghosts floating around Cuba. Brilliant musicians like Compay Segundo of Buena Vista Social Club fame, literary figures like Ernest Hemingway and Federico García Lorca, and bearded-revolutionaries-turned-pop-culture-icons still have a strong presence here long after their deaths. Also present is the political specter Karl Marx so lovingly described in “The Communist Manifesto.”

Former U.S. President George W. Bush called the country an “outpost of tyranny” – along with Burma, Iran, North Korea and others – but the island, which happens to have a higher literacy rate and lower infant mortality rate than the United States, is an excellent destination for Costa Rica-dwelling perpetual visa renewers who are bored of bus trips to the Nicaraguan and Panamanian borders.

The island country has a sort of forbidden charm and is an impressive notch on the belt of any traveler wanting to make friends envious. And things won’t stay this way forever. A recent editorial in Outside magazine estimated that more than 1 million Hawaiian shirt-wearing U.S. tourists would swarm Cuba during the first year that travel restrictions were lifted.

For better or worse, it hasn’t happened yet, but with Costa Rica-based travel agencies lined up to book vacation packages and President Barack Obama cutting the budget for prosecuting U.S. travelers who violate the long-standing trade embargo, there has never been a better time for expat Gringos in Costa Rica – or anybody else, for that matter – to visit Cuba.

Although travelers could spend weeks getting to know Cuba, four days are plenty for a quick introduction via the country’s vibrant capital. Havana, or more correctly La Habana, is a striking city that, compared to the sometimes endearing, sometimes grinding chaos of downtown San José, is a refreshing gulp of air. The country’s only billboards display powerful propaganda, but aside from these, which are surprisingly few and far between, there isn’t a hint of advertising anywhere. The streets are garbage- and pothole-free, and chain-link fences topped with razor wire are notably absent.

Walking around the pedestrian-friendly downtown area, hopping from one historic plaza or museum to the next, is a pleasure in itself. Habaneros, men and women, young and old, are handsome people. Strains of world-class jazz and salsa drift from restaurants, artists display their work from the sidewalks, and little old ladies puff away on monstrous cigars.

An eclectic, and sometimes crumbling, mishmash of colonial and modern architecture looms over the streets. The decay is charming – at least, as charming as exposed rebar can be. Along the Malecón, the seaside walkway/communal front porch to the city, musicians practice their instruments and fishermen toss in their lines. Motorcycles with sidecars rush past, as do clunky, Detroit-built, metal beasts left over from the pre-revolution Batista era.

By late afternoon, when the day’s labor is done, folks take to the streets to kick soccer balls or argue about baseball, the national pastime. For visitors, there’s plenty of nightlife. Ten CUCs or Cuban convertible pesos (about $8) pays for cover charge and two cocktails at the famous Jazz Club La Zorra y El Cuervo in Barrio El Vedado. Every night from 10 p.m. to about 2 a.m., big-name jazz musicians and combos wail and stomp in the crowded, smoky basement. Grab a table by the low stage to get a good view of the show, or sidle up to the bar for unrestricted mojito access.

As if the sensory overload of the city weren’t enough, visitors can hop on a red guagua – Cuban slang for “bus” – at the central plaza bus stop, across the street from the historic Hotel Inglaterra. For three CUCs (about $2.40), you get a day pass to ride back and forth between the city and Santa María del Mar beach, about 30 to 40 minutes east. While the beach’s beauty is undeniable, the whole stretch is crowded with Speedo-clad European tourists and may be less than stimulating to those accustomed to beach bumming in Costa Rica.

Travel agencies will be happy to set tourists up in hotels, but to score a better insight on the ins and outs of Cuban life, don’t stay there any longer than the first night or two. Once you’ve taken to the streets and have a feel for the city, find a casa particular, a government-licensed homestay marked by a blue-and-white sign nailed to the door.

They are all equipped for two people and cost $30 to $50 a night. With no hostels or dormitories in Cuba, casas particulares offer the least expensive accommodations. Shoestringers used to gonzo-ing their way around Central and South America on the cheap should plan accordingly.

Although heavy penalties for robbing tourists have made Cuba quite safe for travelers compared to much of the rest of Latin America (Costa Rica included), scam artists, or jineteros, will do their best to separate you from your money. It’s best to politely ignore anybody who asks, “Where you from, buddy?” They’re in cahoots with bar owners, and unless you want to end up buying overpriced drinks for a table of fast-talking Cubans, you should keep walking. The same goes for deflecting the army of prostitutes eager to participate in the one form of capitalism still rampant in Cuba.

With no sign of how much longer this unique period of Cuban history will last, bragging rights go to those who get to live the experience before the hordes trample their way in. Just don’t post your vacation pictures on Facebook afterward – not if you’re from the U.S., anyway.

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