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.

More than 60 idyllic islands, including Jost Van Dyke, Tortola, Anegada and Virgin Gorda, make up the BVI. Turquoise waters offer thrilling diving, fishing, sailing and swimming. Tortola is the largest island in the volcanic chain and has beautiful beaches and coves, forts, ruins and warm, welcoming people. Virgin Gorda boasts yacht clubs, chic resorts and secluded sands. Coconut palms shade beaches on tiny Jost van Dyke. Sailing is a popular way to travel between islands. Ferries are the other option.

What makes Anguilla's beaches the best in the world? White, powdery sand that stretches for miles, pristine waters and the laid-back, welcoming attitude of the Anguillan people. Swim and sunbathe all day—and all year round—at romantic public beaches like the aptly-named Rendezvous Bay, then dance to calypso music at Anguilla's annual summer festival.

Strongly influenced by the tribal culture of the Guanches (the original inhabitants), Tenerife was conquered by the Spanish 500 years ago. It's home to Mount Teide, Spain's tallest peak, and to the popular beach resort of Los Gigantes. Today visitors flock to Loro Park to see tropical birds, to Tenerife Zoo Monkey Park and to Parque Nacional Las Canadas del Teide's volcanic rock formations. Explore by car or with a "bono bus" ticket, which offers reductions on regular prices.

The sun-drenched Canary Islands lie close to North Africa and have an exotic flavour of their own. Hundreds of volcanoes, rolling sand dunes, rich forests and rugged cliffs dapple these seven Atlantic gems. Catch a ferry to Lanzarote. Ride a camel through volcanic Timanfaya National Park. Take on Tenerife, home of Mount Teide, Spain's tallest peak. Romp Grand Canary's beaches or hike La Gomera's Garajonay National Park. More adventures await on tiny El Hierro, verdant La Palma and peaceful Fuerteventura.

If your kids are sick of the same old beach holiday you take every year, consider taking them to Lanzarote. There are great beaches, to be sure, but this UNESCO World Biosphere reserve has unique attractions and activities. We're talking camel rides on volcanoes (at Timanfaya National Park), or eating at a restaurant in a volcanic cave (at Jameos del Agua). Even the most jaded teens will be impressed.

This former fishing village on Portugal’s southern coast has become a popular resort. Spend a day on Alvor’s main beach, or find one of the smaller, secluded coves along the coastline. In the evening, stroll through the town’s narrow cobblestone streets, dine on fresh local seafood, and enjoy live music at one of the many lively bars.