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.

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.

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.

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.