Just its location—in the Sacred Valley of the Incas—makes Urubamba sound like a mystical, magical place. The snow covered Ch'iqun mountain stands proudly in the background of this Peruvian town that serves as a base for people who want to visit the famous ancient Incan ruins of Machu Picchu. Zip lines and horseback rides let you experience this valley in the Andes in wildly different ways.

The lively capital of Curacao is a welcoming, upbeat destination with two distinct historic districts divided by the lovely St. Anna Bay. Punda, site of neat, narrow streets, is crammed with shops and museums. Otrobanda, or "The Other Side," is a maze of twisting residential streets, contrasting with the organised grid across the bay. Willemstad's colourful colonial architecture has won its UNESCO Heritage site designation. Diving and swimming with dolphins are popular activities in the bay.

Antigua has hundreds of beaches, from the bustling Pigeon Point to the kitesurfing paradise of Jabberwock Beach. It's fun to mix it up—a day spent in a secluded cove, another spent people-watching at a tourist magnet. When you’re tired of sun and sand you can shoot ‘em up at Reservoir Range, where archery and air pistols are a fun way to work out any lingering pre-holiday stress. A tour of the Antigua Distillery is a spirited way to experience a true taste of the island.

You're on island time the moment you set foot in Jamaica. Ocho Rios, a port of call for many cruise lines, also boasts some of the most luxe resorts and spas in the Caribbean. And once you've had your stresses melted away in the island sun, you can head out for a night of dancing and reggae music.

U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the centre of Cuba’s sugar industry.

A city trapped in time, Havana captures the imagination like no other. Faded glamour meets careful colonial-era reconstruction with a backdrop of irresistible colour. Walk El Malecón, the walkway bordering the ocean; visit Old Havana and the Catedral de San Cristóbal; and listen for salsa music, open-air bazaars and parties that last all night.