Sydney, Nova Scotia, Canada

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With its wild landscapes and a Scottish heritage that can be felt at every turn, Cape Breton Island is one of the most unique destinations in Canada. Take a stroll along Sydney’s waterfront and stop for a photo beside the world’s biggest fiddle – a massive nod to the region’s Celtic musical roots at over 60-feet-tall – or head to the Witney Pier Historical Society Museum to learn about the people who immigrated here from all over the world. Sydney is also an ideal base for exploring the Cabot Trail, which is a great place for golfing, kayaking and whale-watching.

St. John, USVI

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The smallest of the three main U.S. Virgin Islands, St. John was an early pioneer in Caribbean eco-tourism. More than half of its 20 square miles are undeveloped — and will stay that way — as they constitute Virgin Islands National Park, created in 1956 from holdings donated by U.S. philanthropist and conservationist Laurance Rockefeller. Much of St. John’s glorious white-sand beaches, coastline and surrounding seas are also protected, either through the park or the Virgin Islands Coral Reef National Monument.

Korčula

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Sitting off the central Dalmatian coast, the wonderfully-green island of Korčula is dotted with olive groves, vineyards and pine forests. The main town’s pretty Old Town exemplifies Croatia’s rich Venetian heritage. At its center, you’ll find the 15th century St. Mark’s Cathedral rising high above the red-roofed Gothic and Renaissance buildings. Go wine-tasting in Smokvica or Cara; soak up some sun on a Lumbarda beach; or take a kayak tour of the islets of the Skoji archipelago – especially Badija, with its pretty monastery.

St. Croix, USVI

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The largest and least-visited of the U.S. Virgin Islands, St. Croix enchants travelers with its unspoiled white-sand beaches, coral reefs, lush tropical landscapes, protected parks and organic farms. Its two relaxed main towns showcase the island’s unique Danish heritage. On the west coast you’ll find Fredriksted, a tiny, tidy grid of a town with a seafront that stretches between an 18th century fort and a wildlife refuge at Sandy Point.

Katakolon

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Tucked into a forested valley in the western Peloponnese, Olympia was ancient Greece’s center for the worship of Zeus, as well as the birthplace of the original Olympic Games. The Games took place here every four years for over 1,100 years, and the ruins – which include a colossal stadium that was built for 20,000 spectators – are truly impressive. Just 20 miles away on the coast is Katakolon, the maritime gateway to Olympia.

Split, Croatia

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Life in this exuberant city revolves around its outstanding UNESCO World Heritage Site, Diocletian’s Palace. Don’t be mistaken though – this is no quiet palace or stuffy museum – it’s an elaborate ancient complex of 220 buildings that make up the beating heart of this beautiful city. Home to around 3,000 people, Diocletian’s Palace is a precious Roman gem where the locals go about their daily lives undeterred by the fact that they’re living in a historical wonder.

Horta, Azores

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Sailing into the famous marina of Horta on the island on Faial is the quintessential yachting experience. This maritime town has been a mid-Atlantic steppingstone for sailors since the Age of Discovery, and today it’s a pitstop for international regattas like Les Sables-Les Açores-Les Sables. Check out the colorful wall on the marina’s breakwater – seafaring superstition states that sailors should paint a message on it to ensure divine protection for their crossing. Take a whale-watching trip or go hiking at Caldeira, a two-kilometer-wide and 400-meter-deep volcanic cone.

Spetses, Greece

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Pine-scented Spetses is an upscale and relaxed island that attracts more affluent Athenians than foreign tourists. With its rich seafaring culture, this little island is also hugely popular with the yachting crowd. This is one of the most cosmopolitan destinations in Greece, with beautiful Neoclassical buildings sitting on its fine squares and horse-drawn carriages roaming its pretty streets.

Siracusa, Sicily, Italy

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Dating back to 734BC, Siracusa was once one of the great ancient capitals of Western civilization. Today it’s a lively city with a charming historic center, lovely Baroque architecture and some amazing Greek and Roman ruins, like the monumental Teatro Greco at the Parco Archeologico – one of Sicily’s most impressive archaeological sites. At Siracusa’s heart you’ll find the beautiful island of Ortygia, which was first inhabited by the ancient Greeks.