Famous touristic landmark Church of the Holy Trinity
Famous touristic landmark Church of the Holy Trinity (Photo: Getty Images/iStockphoto)

How Do I Travel to Cuba as an American?

Famous touristic landmark Church of the Holy Trinity

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Cuba. Where travelers lounge on picturesque beaches, swirl mojitos, dance til sunrise, and cruise back to their hotels in ’57 T-birds. Travelers, yes. But Americans, no. Until 2011, these indulgences were long off limits to U.S. citizens due to a Bay of Pigs–era trade embargo. 

But despite the Obama Administration relaxing travel restrictions, Americans still can’t simply book a flight and show up, beach towel in hand. You’ll have to join education and culture-based excursions on “people-to-people” tours through a licensed company. In many respects, swapping stories with the locals is the best way to discover a destination. However, on these trips, visits to preschools and artists’ collectives often come at the expensive of adventure activities. A few companies fuse both.

Overseas Adventure Travel offers a guided trip that includes meals in local paladares, privately owned restaurants; a visit to Valle de los Ingenios (Valley of the Sugar Mills), a series of interconnected basins with more than 60 refineries that earned the Trinidad area its wealth in the 18th century; and listening to a band playing son, Afro-Cuban music played over a rumba beat. National Geographic Expeditions also visits Trinidad, a colonial city so well preserved that it is a UNESCO World Heritage Site, where you’ll meet a Santería priest.

On Smithsonian Journeys, you’ll meet the farmers at an organipónico (organic farm); visit Ernest Hemingway’s La Finca Vigía, a hilltop estate near Cojimar, the fishing village that inspired his novella The Old Man and the Sea; and follow the path lined with Cuban Royal Palms to the Cienfuegos Botanical Garden, home to more than 2,000 species of tropical and exotic plants.

On Austin Adventures trips, Jose Fuster, called the “Picasso of the Caribbean,” and his son, Alex, will guide you through his studio. You’ll also venture to Valley of the Viñales, a lush landscape where traditional agricultural methods are still used to cultivate tobacco, to roll cigars and add to your humidor at the private finca (plantation) of a local farmer.

Classic Journeys also treks to Valle de Viñales to explore Las Terrazas, a sustainable community in the Sierra del Rosario Biosphere Reserve involved in reforestation. A walk through the rural countryside brings a visit to a working coffee plantation and a curated visit to an orchid garden.

If you want to color outside the lines—the legal lines—Americans can also work around these requirements to travel to Cuba. You can book through tour agencies outside the U.S., such as Australian company Cuban Adventures, which says Americans account for about 20 percent of its business, traveling under general visas from that country. Canadian company Sunlight Tours has also had Americans join their excursions, which offer fishing, kayaking, cycling, and trekking. You’ll be able to enter Cuba with your American passport—it’s coming back to the U.S. with a Cuban stamp that may cause hiccups clearing U.S. customs. After all, you know what the song lyrics say about fighting the law.