Cuba
Cuba is a place that exists outside of time. Walking through Old Havana feels like stepping into a living museum where 1950s American cars cruise past crumbling colonial mansions painted in faded pastels. Salsa music drifts from open doorways. Old men play dominoes on the sidewalk. It is romantic, complicated, and completely unlike any other destination in the Caribbean.
The island is the largest in the Caribbean, roughly the size of Pennsylvania, and sits just 90 miles south of Key West. Despite the proximity, visiting Cuba as an American comes with specific legal requirements that are worth understanding before you book. But the effort is rewarded with an experience that is genuinely unique: a country where the warmth of the people, the rhythm of the music, and the beauty of the architecture create something no other place can replicate.
Where to Go
Havana is the main event. Old Havana (Habana Vieja) is a UNESCO World Heritage Site with colonial plazas, baroque churches, and buildings in every stage of restoration and decay. The Malecon, the seafront promenade, is where Habaneros gather at sunset to socialize, fish, and watch the waves crash against the seawall. The Museo Nacional de Bellas Artes has an excellent collection of Cuban art. And the Fabrica de Arte Cubano is a converted oil factory turned cultural center with live music, art installations, and cocktails.
A classic car tour through the city is a quintessential Havana experience. Restored 1950s Chevrolets, Buicks, and Fords serve as both taxis and tour vehicles, and riding through the streets in a pink convertible with the top down is as fun as it sounds.
Vinales, about two hours west of Havana, is a lush valley surrounded by dramatic limestone mogotes (flat topped hills) and filled with tobacco farms. Tours of working farms let you see how Cuban cigars are made from seed to smoke, and the valley itself is one of the most scenic landscapes in the Caribbean. Horse rides through the countryside and visits to cave systems add to the experience.
Trinidad, a colonial town on the southern coast, is another UNESCO World Heritage Site with cobblestone streets, colorful buildings, and a relaxed atmosphere. The nearby Playa Ancon offers one of the best beaches on the southern coast.
Varadero, east of Havana, is the resort beach strip, with white sand and turquoise water stretching for miles. It is the closest Cuba gets to a traditional beach vacation.
Let Us Plan Your Cuba Trip
Cuba requires more planning than most Caribbean destinations, especially for American travelers navigating the legal requirements. We will help you understand the authorized travel categories, arrange compliant accommodations and activities, and build an itinerary that captures the soul of this extraordinary island while keeping you within the rules.
