Named as one of Canada's 50 Places of a Lifetime by National Geographic, L'Anse aux Meadows transports visitors back in time a thousand years. Perched on the northernmost tip of Newfoundland, the ancient Viking settlement is heralded as the oldest in North America and widely accepted as evidence of European contact here prior to Columbus. Discovered in 1960, L’Anse aux Meadows was named a UNESCO World Heritage site in 1978 and now brings the struggles of early settlers to life.

Surrounded by rugged terrain and lush vegetation, La Romana is home to crystalline waters, white sand beaches and impressive coral reef life. It's a gateway to charming villages such as Bayahibe, ecological trails and numerous golf resorts. In the town center is El Obelisco, painted with images of local Dominican life. Nearby Altos de Chavon is a replica 16th-century village and cultural center featuring artist studios, galleries, an archaeological museum and sweeping views of the Chavon River.

Coastal Slovenia’s largest town, Koper is something of a well-kept secret. Koper’s central core is delightfully medieval and rich in history. Not far from the port, the Old Town centers around Titov Trg, a plaza filled with Venetian-influenced landmarks, from its Gothic-style loggia to the Praetorian Palace and Da Ponte Fountain, a replica of Venice’s famous Rialto Bridge. The Cathedral of The Assumption, also called Koper Cathedral, features a four-story tower with sweeping bay views and houses one of the oldest bells in Slovenia.

Kirkwall is the largest settlement and capital of Orkney, an archipelago in the north of Scotland with history tracing back to Norse times in the 11th century. With history such as this, ancient archaeological sites are the highlight of a visit. The most important monuments can be found at the Heart of Neolithic Orkney, designated a UNESCO World Heritage site. The Ring of Brodgar is one of the finest known truly circular Neolithic stone rings. Other sites that are fascinating to tour are Maeshowe, the Standing Stones of Stenness and the ancient Neolithic village of Skara Brae.

Closer to Cuba than to Miami, the southernmost city in the continental United States can feel like a country all its own. Home to free spirits, scuba divers and six-toed cats, Key West is defined by its quirky charm. People go barefoot, chickens roam the streets and eclectic culture rules. Architecture lovers will appreciate classic Caribbean villas, unique Keys conch houses and Victorian and Queen Anne gingerbread homes. Shopping opportunities range from many music and book shops to trendy designer boutiques.

Of the four main British Virgin Islands, Jost Van Dyke is the smallest. Fewer than 300 residents call its three square miles home, but they extend a warm welcome to the sailors and yachtsmen who drop anchor in Great Harbour and White Bay throughout the year. Life here revolves around the surrounding seas – swimming, snorkeling, fishing and diving – and communing over a tropical cocktail and a freshly caught meal at one of Jost Van Dyke’s legendary beach bars and restaurants. The island’s rugged terrain is crossed with trails.

The site of a Puritan colony established in 1629, Providencia is a remote gem of striking topography, golden beaches and turquoise blue waters. Pirate Henry Morgan made this his base to raid the Spanish empire, and treasure is rumored to be buried here. Far from the Colombian mainland, the island feels more Caribbean than Colombian and more English than Spanish, as Creole is spoken and road signs have English town names.

Just south of La Romana is an island paradise that gives an idea of what these environs were like back in 1698 when pirate William Kidd anchored his ship offshore and fled his English pursuers. While less than six square miles in size, Isla Catalina supports diverse ecosystems including sand dunes, mangrove forests and impressive coral reefs. The entire island is a national park and rich in wildlife with numerous species of birds and tropical fish. Catalina is a haven for diving and snorkeling, and equipment can easily be rented.