Old-School Cool: Traveling to Cuba via Miami

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Ever since Barack Obama reopened diplomatic relations with Cuba, Americans have been wondering: can I go to Havana for my next vacation? The short answer: Yes. The long answer: Yes, but not just to lie on the beach and sip mojitos.

No matter how you get to Cuba or justify your travels there, most will tell you that you should go sooner rather than later, i.e. before the travel restrictions completely ease up and American tourists swarm the island. Whether or not the fears that an influx of Americans will turn it into a Caribbean Disneyland prove to be true or not, now is certainly the chance to catch the Cuba of a past era. And while it still may not be easy, hopping on a plane from Miami to Havana is getting simpler.

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To begin your journey, the best way to start is with a Miami short term rental as home base before setting off to the island. Americans no longer need to request permission from the Office of Foreign Assets Control prior to visiting Cuba, but hopeful visitors do need to justify their travels within one of 12 categories. Those categories include family visits, religious activities, business trips, and more. The easiest way for those who don’t have official business for Cuba travel is through a cultural or educational trip that falls under a “people-to-people” license.

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Many tour companies and non-profits now offer people-to-people tours, with multi-day group tours costing around $3,000-$5,000 a person. And no – that money still doesn’t include beach time and free refills on cuba libres, but it can include anything from museum tours, coffee and tobacco plantation visits to jazz concerts. In order to qualify for the license, the tours need to offer some educational value and include contact with locals, so itineraries are typically jam-packed with activities rather than leisure time.

Most of these trips are weeklong affairs, but for a shorter Cuban getaway from Miami, try Insight Cuba’s Weekend in Havana getaway package. If you prefer a more intensive tour, try Abercombie & Kent or non-profits like Grand Circle Foundation.

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However you plan to justify your visit to Cuba, fortunately there are now daily charter flights from Miami to Havana with airlines like JetBlue and American Airlines. But even though Cuba is just 90 miles from American soil, flights are still relatively expensive and the check-in process can be long. If you prefer to travel by sea, Fathom has recently started offering cruises to Cuba.

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And if you needed a sign that travel to Cuba is about to really take off, consider the fact that hospitality companies are scrambling to plant their own flag on the island. With rooms in government-owned hotels in relatively short supply and casa particulares (private residences) difficult to book, there’s no doubt Americans will be turning to the sharing economy to make their stay in Cuba easier. Keep in mind though that Internet access is scarce across the island, so make all your online arrangements before arriving, and don’t plan on updating your Instagram feed until you’re back in the U.S.

For even more exotic excursions & weekend vacation packages, take a look at our collection of Miami short term rentals. And for additional travel tips and perks, download the Oasis app for iOS or Android.

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Experiential Travel, Miami, Travel Trends, What to do in Miami, Where to stay in Miami

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