Sitting only 90 miles from Key West, Florida, Cuba is a world away from the United States. Majestic natural beauty—white-sand beaches, luminous green-clad mountains, and clear Caribbean seas—is matched by the country’s surreal preservation of the past. The Spanish-colonial grandeur of Habana Vieja may be faded, but it is an authentic bridge between present and past, as much a lived-in neighborhood as open-air museum. Known for iconic images of 1950s-era cars gleaming in classic splendor, other outdated cars are cobbled together in a way that showcases the resilience and innovation of a country that is, at least in part, willfully isolated. Shaped by European colonial powers, pirates and privateers, U.S. intervention and mafia money, revolution, global politics, and largely cut-off from the internet and the wider world, Cuban culture is a vibrant profusion of art and music that moves to its own enchanting rhythm.
Once the crown of the Spanish settlements in the Caribbean, Havana is a city of worn colonial facades and enchanting cultural verve. Spared from the worst of several wars, and then from unconstrained modernization and development by the 1959 Revolution, a sense of stasis and timelessness permeates the city. Stroll the narrow streets of UNESCO-listed Habana Vieja, Old Havana, filled with pedestrians and vendors pushing fruit laden carts, or browse the Plaza de Armas book market on your way to the Castillo de la Real Fuerza maritime museum, housed in a 16th-century fortress. At the heart of Habana Vieja is the Plaza Vieja where the 18th-century Catedral de la Habana presides; stop into the ornate palace of the Museo de la Ciudad to see the building as much as the exhibitions; save time to tour the Parque Histórico Militar Morro-Cabaña, which comprises two complexes of imposing fortifications. Away from the well-preserved Baroque and neoclassical buildings of Habana Vieja, the atmosphere of Centro Habana is definitively more grit than glamour, but possess a charm that’s well-worth experiencing. Wander along the shopping districts of San Rafael and Avenida de Italia, and spend an evening strolling along the enchanting waterfront of the Malecón. Music radiates from all sides, so whether you’re watching a show at the iconic Tropicana or go out on the town dancing, you will find salsa everywhere from small bars to plazas and along the Malecón.
A small city on Cuba’s central southern coast, sitting on a bay of the same name, Cienfuegos is known for its well-preserved colonial architecture and its history as both a French and Spanish port. Laid-back and calm for being a working, somewhat industrial port city, there is no shortage of cultural gems that exhibit the city’s historic importance. A major trading point for sugar, tobacco, and coffee though the 19th century, the city’s prosperity gradually faded when trade with the U.S. replaced European markets—but the collection of palaces, fortifications, and townhouses lining the waterfront Malecón is an indelible stamp of the colonial past. Take a ferry across the bay to the 18th-century Spanish Castillo de Jagua fortress, or duck into the Tomás Terry Theater on the central plaza to see it’s gilded mosaics and ceiling frescoes.
Isla de la Juventud
Decidedly difficult to get to, with underdeveloped infrastructure, a journey to the Isla de la Juventud is not for the faint of heart or the time-crunched traveler. Sitting 60 miles off the southern coast of Cuba, the island’s remote location and untrammeled wilderness are an instant reward. Known as a place once dominated by pirates and privateers, the Island of Youth has a somewhat worn and forgotten feel that sets it at the other end of the spectrum from the bustling beaches and resort luxury of Cuba’s all-inclusives. A third of the island is safeguarded in the National Marine Park of Punta Frances Punta Pedernales, which offers incredible snorkeling and scuba diving—hawksbill turtles, butterfly fish, barracuda, queen triggerfish, and brain coral are just a few of the hundreds of species of marine life of the Canarreos Reef system. The Isla de la Juventud is a place where you can lose yourself in nature, historical legacies—Castro was imprisoned here in 1953—and the lore of lost treasure.
Las Terrazas is a small ecovillage set in the midst of an extensive UNESCO Biosphere Reserve, which encompasses the terraced forest that gives the village its name. The creation of the eco-community was spurred by Fidel Castro’s vision for a green revolution, which entailed carving extensive roads through the mountains, building hundreds of miles of terraces to prevent erosion, and planting millions of trees to reforest the previously logged slopes. After the collapse of the Soviet Union, Las Terrazas opened to tourism to help preserve their community. The only option to stay overnight is the Hotel Moka, but artists’ studios and galleries, restaurants, a network of hiking trails, and a canopy zip-line make for an enjoyable day trip from Havana.
Pinar del Río
Though this city, named for the pines lining the banks of the Río Guamá, has seen better days, its mottled collection of faded colonial and neoclassical architecture offers a glimpse of a Cuba away from main tourist attractions. For anyone searching for an experience that goes beyond the shimmering elegance of Caribbean beaches and restored Old Towns of Trinidad or Havana, Pinar del Río is worth a stop. Once the tobacco capital of the region, with immense plantations in nearby Viñales and Vuelta Abajo, the city held onto the industry even after sugarcane became the island’s predominant export. You can get an up-close look at cigar production at the Fábrica de Tabacos Francisco Donatien before touring the tobacco farms of Viñales Valley. If you want to explore the remote beaches, lagoons, and forests of Parque Nacional Peninsula de Guanahacabibes on the western tip of Cuba, stopping for an afternoon in Pinar del Río breaks up the journey nicely.
Santiago de Cuba
Closer geographically to Haiti than to Havana, Santiago dances to a boisterous rhythm blending Spanish, Afro-Cuban, and other European influences. Historic monuments are plentiful, and can fill days of urban exploring—visit the Antiguo Cuartel Moncada, where Castro’s first attempt at revolution failed, or wander through the colonial mansions of Barrio Tivoli. Visit the imposing fortress overlooking the harbor, Castillo del Morro, designed by the same Italian architect responsible for the massive forts of Havana. And for a taste of history and a cold drink, stop into the bar of the Fábrica de ron Caney distillery, where Bacardi rum began its global ascent back in 1862. The true reward for traveling to the far southeastern tip of Cuba, however, is the majestic range of mountains that come crashing down to meet the Caribbean. A range of hikes will take you through the forests and to the peaks of Gran Parque Nacional Sierra Maestra and Parque Nacional Turquino; or you can opt for equally impressive vistas accessible by roads through Parque Nacional de Gran Piedra to the east.
In a country that often feels trapped in time, Trinidad is the crowning jewel of colonial culture and architecture. An enchanting town on the southern coast of central Cuba, Trinidad’s web of cobblestone streets and colonial buildings around its neo-Baroque Plaza Mayor is a well-preserved window into the past. Though its compact nature means that you can tour the Old Town in an afternoon, the region outside of town is bursting with history and spectacular nature worth sticking around for. The Valle de los Ingenios is a string of historic sugar mills and plantations that showcases grand estates and the industry’s impact in the 18th and 19th centuries. Nearby, the Parque Natural Topes de Collantes in the Sierra del Escambray is a lush reserve with hiking trails and waterfalls. To the south, you can stretch out on Playa Ancón, one of the south coast’s most exquisite beaches.
The narrow finger of the 13-mile-long Hicacos Peninsula, to the east of Havana, is the all-inclusive capital of Cuba. Growing to international renown during the sumptuous years of 20th century sugar barons and mafia influence, Varadero—which generally refers to the whole peninsula—is home to miles of virtually unbroken palm-fringed, silky-white sands lining transcendent seas. The central area around the town of Varadero tends to see the most beach traffic, so head to the luxury resorts of the eastern tip of the peninsula for a more remote atmosphere—here you can also visit the ancient burial caves of the Reserva Ecológica Varahicacos. This region doesn’t boast the vibrant local culture of Havana or other more traditional towns, but if you are looking to relax in style and soak up the sun, Varadero is the perfect place.
The small town of Viñales in western Cuba has a well-established tourist economy that somehow doesn’t seem to even wrinkle its laid-back, traditional, and unimposing atmosphere. Colorfully-painted houses line the streets and shaded porches are the mainstay of the social scene; the town has a slew of quality restaurants and casas particulares—private houses with guest-rooms—but it’s the otherworldly landscape that draws people to this UNESCO-listed valley. Hike among traditional tobacco and cassava farms, where the dusty roads and cultivated fields are a rusted red hue, through terrain punctuated by towering limestone hills called mogotes. Cycle, go horseback-riding, or wander under your own steam—the valley is also known as a premier rock-climbing destination.
Almost entirely devoid of people, the swampy green wilderness of the Zapata Peninsula is a wonder for bird-watching and outdoor-enthusiasts. The majority of the peninsula, which makes up a large portion of the central state of Matanzas, is protected as a UNESCO Biosphere Reserve called the Parque Nacional Ciénaga de Zapata, or the Zapata Swamp National Park. There are 190 documented bird species in the park, 21 of them endemic to Cuba—great hiking and an impressive array of colorful species like flamingos, tocororo, and bee hummingbirds make this an alluring destination not only for serious birders. For less humid pursuits, head to the remote beaches of Playa Larga and Playa Girón along the Bay of Pigs, where the coast drops off dramatically, making this a haven for scuba diving and snorkeling.