Traveling in Cuba will change the way your family sees—and lives in—the world. In just seven days, you trace 500 years of momentous history, have person-to-person interactions with everyday Cubans, and experience the country in exciting and unexpected ways. There’s 16th century Trinidad, where you see the relics of colonialism, slavery and the sugar trade and go for a rainforest walk to a family-owned coffee plantation. A local guides you through the pastel Caribbean streetscape of Cienfuegos, founded by immigrants from France and Louisiana in the 1800s. On the Bay of Pigs, you return to the mid-century Revolution and the perils of the Cold War (and snorkel in the warm waters over an amazing coral reef). And all of those centuries compete for attention in Havana where you cruise in restored 1950s tail-finned cars, shop in a local market, meet cigar-rollers and dancers, visit the home of Ernest Hemingway, and more. Beginning to end, you will all see and share moments that spark your curiosity and alter your perceptions.

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DAYS 1-4 - HAVANA AND THE BAY OF PIGS
For a real-life look at everyday Cuban life, chat with the locals as they shop farmers’ stalls at an organic market. You’ll be welcomed into a traditional cigar-making factory where a friend who is an aficionado fills you in on the role of the trade in Cuban life. Explore Cuba-U.S. history with a former Cuban diplomat. Meet the husband-and-wife team whose independent small business specializes in restoring classic cars. Then their craftsmen take you for a tail-finned spin through the streets of Havana. You also have chances to chat with a photojournalist who documented Castro’s life and cook in a chef’s private home followed by lunch in the family dining room. Your time in Havana is capped with a visit to Finca Vigia, Ernest Hemingway’s Cuban home.

En route to Trinidad, you’ll stop at the Bay of Pigs for a chance to snorkel on the pristine coral reef that saw the failed 1961 invasion; a naturalist will introduce you to the rich habitat of the Zapata peninsula.

DAYS 5-7 - TRINIDAD AND CIENFUEGOS
In the Valley of the Sugar Mills, meander amid the ruins of 19th-century sugar plantations. A local leads you on a visit of 500-year-old Trinidad, and you'll get a rumba lesson at a private dance studio. In the Escambray Mountains near Trinidad, the next generation of a family of coffee-growers welcomes you to their plantation to see how coffee is grown and processed and to share a tasting with you.

On your final morning, join a local historian for a personal look at Cienfuegos, the pastel city known as the “Pearl of the South.” Late afternoon, you will reach Havana for your homebound flight.