Ponta Delgada, São Miguel Island, Azores, Portugal

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With its elegant architecture, cobblestoned streets and restaurant-lined marina, Ponta Delgada on the island of São Miguel is the charming capital of the Azores. See the three-arched Ponta Delgada, which dates back to 1783; sample local cheeses in the Mercado da Graça; or stop to smell the flowers in Antonio Borges Garden. Venture outside the city and you’ll never forget the view from the Mirador do Rei lookout.

Ephesus (Kuşadasi)

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Simple seaside pleasures – a waterfront promenade, open-air cafés and some gorgeous beaches – are the focus of life in the resort town of Kuşadası. This modern port is the gateway to Ephesus, one of the great cities of antiquity, which lies just 10 miles inland. Founded by the Ionian Greeks, Ephesus flourished as a provincial capital of Imperial Rome. Wandering around its agoras, baths, libraries and mosaic-adorned houses is an experience you’ll never forget.

Nice, France

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Set between the beautiful Baie des Anges and the Alps, the sunny capital of la Côte d’Azur has long been admired for its beauty and sophistication. One of France’s oldest cities, Nice blends its urban verve with plenty of seaside charm, a fantastic local food scene and a heritage that’s steeped in pretty Italianate influences. In the narrow streets of Vieille Ville you’ll find charming piazzettas, cozy cafés, traditional stores and a famous flower and grocery market.

Milos, Greece

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One of the most geographically distinctive and culturally rich islands in the Cyclades, Milos is a volcanic island of beautiful beaches, thermal springs and unusual rock formations. Adámantas, the island’s pretty port and nightlife hub, is sheltered inside the volcano’s former caldera. Plaka, the nearby capital, overlooks the entrance to the Gulf of Milos.  This charming hilltop town is home to Plaka Castle with views of the entire island as well as an acclaimed archaeological museum, which features a replica of the island’s most famous find: the Venus of Milo.

Les Anses-d'Arlet, Martinique

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The island of Martinique provides a little slice of French sophistication in the crystal-clear Caribbean. Sail into Les Anses-d’Arlet, a charming string of villages framed by lush green hills and some of the island’s best beaches.  Soak in the rich history at the Fort Saint-Louis or the Saint-Louis Cathédrale.  Pull up a chair and watch the colorful boats bob in the bay as you dine on a delicious blend of French and Creole-inspired cuisine.

Colón

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Settled right at the Atlantic entrance to the Panamá Canal, Colón is Panama’s gateway to the Caribbean, where the culture is shaped by its history. The ruins of Fort San Lorenzo, a UNESCO World Heritage Site, tells stories of over 400 years of military history. From the Agua Clara Visitor Center, learn all about the canal from the technology to the history and how the canal unites the world. Opportunities for outdoor adventures are plenty at La Granja Campo y Aventura, the adventure park through the rainforest, featuring canopy ziplines, horseback rides and kayaking tours.

Deshaies

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Thanks to its sheltered bay, Deshaies is a popular pitstop for yachters from across the globe, which gives this pretty little fishing village a surprisingly chic, cosmopolitan air. The city is home to the wonderful Jardin Botanique, a tranquil showcase of tropical flora. It’s also just minutes from the soft sands of the Grande Anse and Plage de la Perle. The Caribbean coastline is dotted with glorious beaches, as well as world class diving and snorkeling spots, such as the renowned Cousteau Reserve.

Korčula, Croatia

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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.

Katakolon, Greece

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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.

Horta, Azores, Portugal

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Known as the ‘Pearl of the Atlantic’, the volcanic island of Madeira is bursting with exotic colors. The capital city of Funchal is a place to lose yourself in old alleyways, street cafés and pretty squares. See Gothic and Romanesque styles blend at Funchal Cathedral; explore the Contemporary Art Museum, which is housed in the mighty 17th century São Tiago Fortress; or join the locals in the Mercado dos Lavradores, which is adorned with beautiful hand-painted tiles. In the evening, check out the funky Zona Velha.