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.

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.

Bracing and beautiful, this tiny fishing town on the Gulf of Saint Lawrence’s rugged coastline was settled by the Acadians in 1857 – which accounts for the lovely lyrical lilt of the local accent.

Sitting off Panama’s northeast Caribbean coast, Guna Yala is a stunning archipelago of 365 palm-fringed islands. An autonomous province since 1924, this intriguing, eco-conscious destination is governed by the indigenous Guna people. A paradise of white sand beaches, thatched houses and turquoise waters, life is refreshingly uncomplicated in Guna Yala. While the locals have embraced outboard motors and mobile phones, they mostly live like their ancestors did.

Gallipoli means ‘Beautiful City’ in Greek—and this gorgeous little town on the Salento Peninsula certainly lives up to its name. Surrounded by water and accessible only by sea or via a 16th century bridge, the town’s historic heart sits on a small island that juts out into the Ionian Sea. This is a place that displays its proud seafaring heritage at every turn, and you’ll see fishermen fixing their nets at the harbor and the freshest seafood dishes adorning the menus of the Old Town.

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.

Green, forested Kefalonia is an Ionian idyll amid cerulean seas: an island of hidden coves and beaches and scenic villages and vineyards. On its northeastern shore, the tiny port of Fiskardo welcomes luxury vessels to its pretty, curved harbor that looks out over the legendary island of Ithaka. Colorful Italianate villas line Fiskardo’s waterfront, creating a beautiful setting for the village’s impressive line-up of chic cafés, restaurants and boutiques.

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.

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.

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.