Packed to the gills with antique silver, porcelain and furniture, the red sandstone Brodick Castle is one of the highlights of the Isle of Arran. The castle overlooks Goatfell, a majestic hill that’s a popular day hike. The Machrie Moor stone circles make for a mystical field trip, as does a tour of The Arran Malt whisky distillery.

Get the experience of visiting two island colonies in the same 37 square miles. Saint Maarten/Saint Martin's spicy marriage of Caribbean, French and Dutch cultures matches its physical diversity: the island is both urban and untamed, with rain forest-like landscapes, white beaches, and amazing caves and wildlife.

This Gallic toehold in the Caribbean exudes a distinctly French air, enticingly spiced up by West Indian warmth. Local culture and cuisine combine both influences. The stylish isle is dominated by Mount Pelée, which destroyed the city of St Pierre in 1902. Black sand beaches and rainforests are found in the north, with yet more beautiful sands to the south. Sights include La Pagerie, birthplace of Napoleon's Empress Joséphine, and Diamond Rock, a 600-foot pinnacle that was once registered as a British warship.

Home to palm-lined beaches, tranquil coral reefs, and several top-tier hotels, it’s no wonder why Bavaro is one of the Dominican Republic’s most popular destinations. This resort hub combines convenience and Caribbean culture with an impressive range of activities across its expansive coastline.

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.

Cuba's top beach destination sits on a 13-mile-long peninsula with powder soft sands lapped by waters of the Kawama Channel. Resort hotels teem along the shore that U.S. celebrities and gangsters, including Capone, discovered in the 1920s. Clubs and bars provide mojitos and merriment, after long days baking on the beach, golfing, diving or deep sea fishing. Rent a scooter or hop aboard an open-air tourist train or bus to see more of this stunning spot. Caves, keys and virgin forest add to the area's allure.

Jamaica is a melting pot of African, Asian, European and Middle Eastern cultures. You'll experience this diversity in its strong crafts tradition, performing arts and distinctive dining options, like ackee and saltfish with roast breadfruit. Take your holiday to new heights at famed cliff jumping spot, Negril Cliffs. Jamaica offers long beaches, protected coves, rugged mountains, waterfalls, caves and sunshine and chances to play in the surf, ride horses and swim with dolphins. Jump in!