Jost Van Dyke, BVI

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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.

Providencia, Colombia

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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.

Isla Catalina, Dominican Republic

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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.

Invergordon, Scotland, UK

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The friendly village of Invergordon is your gateway to the Scottish Highlands. Visit Cawdor Castle, built in the 14th century and considered one of the most stately homes in the Highlands. The founding family, the Thanes of Cawdor, live there to this day. Next up is Dunrobin Castle, the ancestral home of the Clan Sutherland and one of the oldest inhabited houses in Scotland, featuring stunning formal gardens that run down to the sea.

Ibiza, Balearic Islands, Spain

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One of Europe's favorite playgrounds, Ibiza boasts more than 100 miles of coastline frosted with exquisite beaches. It's a hub of sun worship, white sand, beach bars and clubs that buzz all night. And there's history too. The fortified Old Town, known as Dalt Vila, is a UNESCO World Heritage site and a spectacular example of Renaissance military architecture. Carrer del Calvari leads to Portal Nou, the entrance through the old city walls, and a walk up the hill reveals panoramic views of the city.

Hvar, Croatia

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Super yachts crowd the harbor and waterside bars hum with wealthy vacationers and young partiers in this posh island getaway with a laid-back Mediterranean vibe. The island of Hvar is famous for its lavender fields, vineyards, year-round sunshine and nonstop nightlife, but it’s also rich in culture and history. Near the harbor stands a Benedictine convent where nuns fashion lace as part of a 150-year-old tradition recognized by UNESCO as an Intangible Cultural Heritage.

Honfleur, France

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Situated where the Seine estuary meets the English Channel, Honfleur has been an important port of trade and defense for centuries. Tall, narrow buildings line cobblestone streets in the Vieux Bassin, the historic harbor, and attract Parisians on summer weekends. Look up for the 15th-century wooden spire of the Église Saint-Étienne, the oldest church in town and now a maritime museum. Contrast it with the Église Sainte-Catherine, built entirely of wood by the town’s shipbuilders. Honfleur has a long tradition of inspiring artists in the impressionist school.

Helsingborg, Sweden

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Just across the strait from Denmark, the coastal Swedish city of Helsingborg has earned a reputation as the friendliest city in Sweden. The city’s most prominent landmark is Kärnan Castle, built by the Danes in the 1300s and destroyed in 1679. All that remains is a defensive tower that looms over the city. Also worth visiting is Sofiero Castle, which lies in one of Europe’s most beautiful parks and was once the summer getaway for Swedish royalty. There are handsome Gothic churches, a Neo-Gothic Town Hall and even impressive contemporary buildings, all easy to see on foot.

Heimaey Island, Iceland

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The largest of the Westman Islands off the Icelandic coast, Heimaey is best known for a volcanic eruption in 1973 from a previously unknown fissure that rained ash and lava and changed the landscape forever. A heroic effort was made to save the town – and the valuable frozen fish stock stored at the pier – by pouring seawater on the molten lava. This slowed the red-hot lava’s march toward the sea, and all residents were able to escape. In time, residents were able to return and rebuild the community, now situated amidst the lush landscape of volcanic peaks.

Halifax, Nova Scotia, Canada

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A major economic center of Atlantic Canada, Halifax is also all about culture and scenery. And history. And shopping. And food. Active travelers will enjoy a hike along nearby Peggy's Cove to see the iconic lighthouse, or a Segway tour through Halifax proper, or even a kayak through the harbor. With miles of coastline, Halifax has some of the best views in Nova Scotia, and the national historic site of Halifax Citadel is one of the best places to take in these scenic vistas.