With its sandy North Shore beaches, rocky outcrops, green parks, hemlock woods and wild estuaries full of shorebirds, it is no wonder that Gloucester has attracted such a rich and diverse artists' community. Fitz Hugh Lane, Winslow Homer and John Sloan are just some of the artists who have taken inspiration from Gloucester's beautiful surrounds. Still boasting dozens of galleries and boutiques, as well as museums, theaters and an artists' colony, the city's art scene clearly continues to thrive.

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 center of Cuba’s sugar industry.

Drawn by year-round warm weather, colonial-era architecture and the freshwater Lake Nicaragua, travelers from around the world are flocking to Granada. Eco-tourists will love visiting the dormant Mombacho volcano, sailing on the lake and ziplining through the trees. Fans of spa treatments and shopping will find plenty to do, too.

The landscape is dramatic—even a bit moody, with the Cuillin Range in the background—but outdoorsy kids will have a blast on the Isle of Skye. Plenty of water sports are available, and you’ll also find great hiking and even pony rides. Portree, the largest town, makes a great base for exploring this striking island.