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havana - cuba 1For a minute, let’s remove those Cuban stereotypes – you know, Castro, communism, and Teddy Roosevelt riding through Santiago, Cuba like the mustached maven portrayed in Night at the Museum. For decades, while America upheld its embargo on Cuba, millions of tourists from Canada and western Europe have flocked to the white sandy beaches at Jardines del Ray, or strolled the cobblestone streets in colonial Trinidad.

But things are rapidly changing: already, in the first third of 2014, Cuba’s seen more American tourists than Germans, Brits, and French visitors from all of last year, accounting for the second highest tourism earnings behind Canada. But that doesn’t mean traveling to Cuba from the U.S. is suddenly easy: the U.S. still holds a fifty-year trade embargo on the communist nation, and, without the guise of a foreign passport (or perhaps a fake Canadian accent), navigating those 90 miles south of Florida requires careful planning. Here’s how to do it…

Recent enactments allow Americans more ways to legally travel to Cuba. According to the revamped restrictions, Cuban-Americans can travel back to their home-country as long as they have proof of familial residency. But what if you’re not Cuban-American? Technically speaking, it’s illegal to travel to Cuba for “tourism” purposes, so tourists must travel through a permissible “People-to-People” program, which holds an official license from the U.S. State Department.

Unlike most vacations, the Cuban People-to-People program prohibits purely recreational activities, focusing instead on the island’s academic and cultural pursuits, including visits to hospitals, music studios, tobacco farms, historical sites, or even a Community Party meeting. With the aim of bringing Cubans and Americans together, these tours eschew lounging on the beach and sipping mojitos in favor of more structured itineraries.

Americans who book these tours can expect full days uncovering all walks of Cuban life, by means of educational interactions. One minute, you will be discussing cultivation with a local tobacco farmer, while the next day might include a traditional musical performance at the Museo de Artes Decorativos. The idea is to gain insight into U.S.-Cuba relations from the opposite point-of-view. Sure, you might end up missing out on  regular vacation activities like… doing nothing. On the flip side, you’ll explore a part of the world few tourists — let alone Americans — have.

What you need to know before booking a tour:

  • Bring a valid passport. Your chosen People-to-People tour company has your visa covered; its required by law.

  • Bring cash. Most U.S. credit and debit cards don’t work in Cuba, and U.S. currency is accepted everywhere. You’ll want around $50 cash per day. A quick warning: There’s a $25 CUC departure tax, which cannot be paid in U.S. dollars, to be paid at the airport upon check-in for your departure. Some tour operators cover this for you, so you won’t have to worry about it.

  • No U.S. embassy exists in Cuba. If you get in serious trouble, you’re on your own.

  • Speaking of getting in trouble, your American insurance may not be acknowledged at hospitals if you fall ill while on the island. Luckily for you, many vacation packagers cover Cuban health insurance.

  • It’s okay to return with souvenirs like art, clothing, and a cute key chain, but, sadly, it’s illegal to return with fresh coffee, hand-rolled Cuban cigars, or a pint of real Havana Club rum.

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