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How to Travel to Cuba

Cuba. The Caribbean island that has inspired singers, writers and visionaries. With its beautiful beaches, tropical climate and famous cigars, Cuba is a seemingly ideal travel location. However, though Cuba was a popular tourist destination for Americans for decades, around the 50s, after the Cuban Revolution, chilly relations between the two countries made travel there difficult. For a long time, Americans who wanted to visit had to obtain special visas, were limited to specific--and expensive--guided tours, programs that often left them under close scrutiny of both governments. Many tourists and visitors resorted to traveling to Cuba via other countries, such as Canada or Mexico, as these countries had warmer ties with the island.

The appeal of a Cuban vacation did not diminish with time, despite strained interactions between the United States and the island. In fact, with a number of Cuban citizens immigrating to the States, strong cultural ties have been established, with Cuban restaurants and other establishments opening up throughout the country. Many would love to see the country for themselves or to visit friends and family still living there. If you fall into either of those categories, or simply want to check the country off your bucket list, but are stymied when it comes to getting there, have no fear: you can get to Cuba these days, though depending on your nationality or reasons for travel, it may take some creativity to get there.

General Travelers

Visitors to Cuba from pretty much every country on the globe outside of the US have no problems going to Cuba. In fact, a third of Cuban tourism is made up of Canadians, who enjoy particularly happy relations with the island. So long as you have your regular travel documents in order, such as the necessary passport and visas, you can travel via plane or boat and enjoy the country’s tours and attractions without problem or restriction. There are regular flights to Cuba out of Montreal, Toronto and Cancun, for those living in North America, and most European airports offer flights there as well.

One thing to bear in mind, though, when planning your Cuban vacation, is the weather. Generally, Cuba has a mild, beautiful climate, perfect for lazy beach days. Still, there is a rainy season to be aware of so that you can maximize your out-of-doors time while on the island. The rainy season starts in May and goes through October every year, with severe storms and hurricanes typically occurring between September and October. During that time, many areas of the island flood or experience damage. If possible, plan your trip during the remaining months of the year, especially if you’re traveling to Cuba via ocean cruise.

American Travelers

Before the Revolution, Americans and Cubans got along well, engaging in mutual trade and commerce. However, after the Revolution, things quickly soured between the two countries and each elected president from Kennedy onward tightened restrictions and embargoes on the island, particularly aimed at import/export and travel.

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For a short period of time, these restrictions against travel to Cuba for American citizens were lifted under the Obama administration. In 2014, President Obama got rid of most of the limitations on American-Cuban travel and tourism. The only real restriction that remained was the legal requirement to keep a travel log that detailed a tourist’s movements and interactions while in Cuba, but even this law was not strictly enforced by the American government at that time. For a short period, things were looking up for American citizens who wanted to enjoy a relaxing Caribbean vacation on the beautiful island of Cuba.

However, this travel freedom did not last long, as by 2017 the Trump administration renewed many of the old restrictions based on possible attacks on the American Embassy in Havana. Officially, travel to Cuba is strongly warned against by Homeland Security for the safety of American citizens. American Visas for Cuban travel are only officially granted if you fall into one of twelve categories of travelers:

  1. People visiting family members

  2. Visitors on official US government, foreign government, and intergovernmental business

  3. Journalists

  4. Researchers

  5. Travelers engaging in educational activities

  6. Travelers engaging in religious activities

  7. Public performers, people coming to work in clinics, workshops, or competitions/exhibitions

  8. Humanitarian workers

  9. People visiting in order to directly help the Cuban people

  10. Visitors promoting activities for foundations, research organizations or educational institutions

  11. Export or import workers

  12. Certain other authorized export activities.

If you fall into one of these categories, you should be able to obtain a license that will allow you to travel to the island. However, you’ll still be subject to additional restrictions. American tourists and travelers in Cuba may not make any financial transactions with any business that is linked to the Cuban military. This cuts out a lot of state-run restaurants, tours and hotels, as many are nationally funded. You can still sign up to stay in privately run hostels, hotels and bed and breakfasts, and can sign up for cruises and tours via privately owned companies or ones based in the United States. In fact, if you are having trouble obtaining a visa for Cuban travel because you don’t strictly fall into one of the above twelve categories, travel experts recommend signing up for an official cruise as most American-Cuban cruise companies know the restrictions well and have set their businesses up to work with and around the red tape. They’ll often take care of all the details for you. Two particular popular and successful cruises to Cuba are Carnival and Oceania Cruise which operate out of Miami.

Another benefit for American citizens to go to Cuba with an official tour group or cruise, instead of attempting solo travel to the island, is that tour and cruise companies will make itinerary reports to fulfill the government requirement to document your trip. If you go it alone, you’ll have to keep careful records of where you went and when along with all of your receipts. Though you may not be asked for these records immediately upon your return, the government requires you keep them for a minimum of five years, and you’ll need to produce them if t