From Christopher Columbus’ trip in 1492 to the Bay of Pigs and beyond, Cuba has seen its fair share of historic events. With the restrictions on American visits significantly relaxing as of January 16, it might be a good time to consider everything the nation once known as the "Pearl of the Antilles" has to offer. American travel to Cuba must still fall within 12 categories—including religious, educational, cultural, professional, journalistic or humanitarian activities—although the administration says there will now be fewer hoops to jump through, and Americans will be able to spend money more freely within the country.
"Cuba boasts some of the oldest cities in the hemisphere," says Emilio Cueto, a researcher specializing in Cuban culture who advises the Smithsonian Journeys excursions. "To travel to Cuba is to travel in many directions and throughout many heritages."
Here are our picks for the sites that tell Cuba’s story, from its days as the staging area for Spanish explorations of the Americas to the tumultuous political events of the 20th century.
Founded by the Spanish in 1519 and once the largest port in the region, Havana's historic city center retains an time-warped, atmospheric allure. Bounded by the original city walls and marked by five large plazas (each with its own architectural style), Old Havana is a mix of Baroque and neoclassical monuments and narrow streets lined by private homes. Highlights include the baroque Catedral de San Cristóbal (one of the oldest cathedrals in the Americas, and once home to the remains of Christopher Columbus) and the Castillo de la Real Fuerza (the oldest extant colonial fortress in the Americas). UNESCO has designated all of Old Havana a World Heritage site, alongside its vast network of centuries-old defensive installations—which include some of the biggest and the oldest stone fortifications still standing anywhere in the Americas.
Parque Histórico Morro y Cabaña, Havana
The main attractions at this historic park across the harbor from Old Havana are two serious fortresses: Morro Castle (popularly known as "El Morro") and La Fortaleza de San Carlos de la Cabaña (aka "La Cabaña"). Built by the Spanish beginning in 1589 to protect against pirates, the picturesque El Morro now houses a series of mini-museums. Visitors can also explore the ramparts, barracks, and a still-working lighthouse, and enjoy stunning views of Havana and beyond.
Located across a deep ravine, La Cabaña, built in the 18th century, functions almost as a miniature city. (Che Guevara used it as his command post in 1959, a fact commemorated in one of the most popular exhibition halls.) It even has its own cigar shop. Every night, an honor guard in 18th-century military dress fires one of the fort's canons, creating a deafening blast before a crowd that can swell up to a thousand people.
Tucked within the central Cuban province of Sancti Spíritus, the 16th century city of Trinidad is a triumph of historic preservation—scholars say its maze of pastel mansions and churches forms one of the best collections of colonial architecture in the Americas. The city owes many of its buildings to the heyday of the sugar industry, which flourished nearby from the late 18th century to late 19th century. The whole town (and the nearby Valley de los Ingenios, or Valley of the Sugar Mills) is a UNESCO heritage site, not to mention an extremely picturesque photo op, but the elegant Plaza Mayor is one the top attractions—it includes the neoclassical-style Palacio Cantero, which houses the municipal history museum and a chance for some spectacular views.
Comandancia de la Plata, Gran Parque Nacional Sierra Maestra
Perched atop a mountain ridge usually shrouded by mist, this was the rebel headquarters Fidel Castro established in 1958 while fighting against the Batista government. Getting there involves a four-hour climb through the woods, but it’s probably worth it: the camp remains much as Fidel left it. The main attraction is probably Casa de Fidel (Fidel's House), which includes no less than seven secret escape routes. There’s also a museum, a radio building that transmitted rebel broadcasts, rebel huts, and a primitive hospital founded by Che Guevara.
Playa Girón, Matanzas
Although Americans will forever associate the Bay of Pigs with the botched CIA-backed invasion of 1961, Cubans are more likely to think of the area known as Playa Girón as a relaxing vacation spot. Tom Miller, author of Trading with the Enemy: A Yankee Travels through Castro’s Cuba, says the site is one of his favorite historic places in the country: “Growing up in the United States, the words 'Bay of Pigs' signify everything that can go wrong politically and militarily. Yet when you arrive at the beachfront Cubans call Playa Girón, the place is actually sunny and cheerful. In crab migration season your car might crunch a few crustaceans as they crawl across the highway.” A small museum offers detailed exhibits explaining just how badly things went awry for the Americans in 1961, although some tourists prefer to focus on the scuba diving and snorkelling options.
La Finca Vigía, San Francisco de Paula
Ernest Hemingway lived at this hilltop estate (the name translates to "Lookout House") for more than 20 years, writing several of his classic novels there, including For Whom the Bell Tolls and The Old Man and the Sea. It’s now a museum featuring Hemmingway's original furniture, artwork, 9,000 of his books and memorabilia. Miller says, "In all my travels, I've found Finca Vigía the best place I have ever seen to write. Ernest Hemingway's Cuban home has moist Caribbean air, a view of the city miles away, a gently sloping front yard, as well as sturdy trees with protective shade, a friendly neighborhood, and sweet sunlight. And that's just outside. There's also the design of the house, solid bookshelves, well-placed windows, a living room with its phonograph—and two minutes away on foot, the swimming pool for a sunrise dip. Finca Vigía is both practical and romantic."
Monumento Ernesto Che Guevara, Santa Clara
This is the final resting place for Ernesto "Che" Guevara, buried at the site in 1997 after his remains were discovered in formerly secret location in Bolivia. The location features a massive bronze sculpture of Che above a museum and mausoleum. Bob Guild, vice president of Marazul Charters, which has been arranging visits to Cuba for 35 years, says the spot is among his favorite historic locations in the country: "The mausoleum and small museum are done with great taste, and always seem to be visited by thousands of young students from Cuba."
Casa Velázquez (Museo de Ambiente Historico Cubano), Santiago de Cuba
Built in the early 16th century to serve as the official residence of the island's first governor, the Spanish conquistador Diego Velázquez, this is the oldest house still standing in Cuba—and one of the oldest in the Americas. The magnificently preserved building now houses the Museo de Ambiente Historico Cubano, a museum of decorations and furnishings from the 16th to the 19th century, as well as former gold foundry on the first floor.