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Boasting a UNESCO World Heritage Site since 1988, Trinidad is a veritable open-air museum of Spanish colonial architecture, and most likely how your idyll in Cuba looks like. Nowhere else on the island is the Cuban way of life more evident: vibrant colors, storybook architecture and locals socializing on ancient cobblestone streets. But aside from its picture-perfect looks, Trinidad revels in the best of both worlds.

2016 was a great year for Viñales and with good reason. A lush region in Pinar del Rio province, this Cuban West of sorts offers a rich natural habitat, favorable for a wealth of outdoor activities. Known for its leading role in sustainable agriculture and tobacco farming, Viñales Valley is blessed with more than its exceptional limestone formations, mogotes, and ecological plantations.

Havana is Cuba’s capital city and home to more than two million inhabitants. It sits at the mouth of Havana Bay on the Northwest edge of the Caribbean island. Most who have traveled to Havana, or have looked into it, are already well aware of the wonders of the city’s Old Havana district. Sweet Cuban melodies and the fragrant aroma of coffee drift out from living rooms and cafés into cobblestone alleyways.

Founded in 1819 by French settlers from Bordeaux and Louisiana on the coast of South-central Cuba, Cienfuegos (literal translation “one hundred fires”) is the only Cuban city with an entirely distinct character and urban layout.

This cookie-shaped island-off-an-island, 60 miles from Cuba’s mainland, is the country’s largest in land mass (934 square miles; 31 in diameter), but smallest in population (fewer than 100,000). Its slow pace belies its tumultuous past.  

This special municipality knows little tourism, but serves as a popular summertime getaway for mainland Cubans and underwater explorers. Lush coral reefs, exotic fish species, and advanced SCUBA facilities reward adventurous divers.

About a half an hour’s drive from Havana sits the little fishing village of Cojimar. Inseparable from the lore and legends of Ernest Hemingway, the town on the Bay of Cojimar still echoes with the author’s influence.

A bust of the writer stands at the town’s Hemingway Memorial, and an annual fishing tournament honors his memory. Visitors can dine on seafood at La Terraza, as Hemingway did when he lived in Cuba from 1939 to 1960.