Over the centuries Romans, medieval Catalan kings and the French Royal Navy have all sailed into the deep, natural harbor of Port-Vendres in Roussillon – the French part of Catalonia. Just up the coast from this working fishing port, you’ll find the colorful seaside village of Collioure, which has inspired artists like Henri Matisse and Picasso and is one of the most picturesque resorts on the Côte Vermeille.

The second largest of Spain’s Balearic Islands, Menorca boasts more beaches than Majorca, Ibiza and Formentera combined.  What’s more, this ecologically-minded island has managed to remain utterly unspoiled, as UNESCO declared it a Biosphere Reserve in 1993, and it remains protected to this day. Take a stroll in the town of Ciutadella, the island’s former longtime capital, and you’ll find a beautiful historic quarter where the narrow medieval streets invite exploration.

Sitting on the deep, aquamarine waters of Man O’War Bay, the pretty fishing village of Charlotteville is one of Tobago’s oldest and most laid-back settlements. The off-the-beaten-track location and relaxed, beachy ambiance are at the heart of Charlotteville’s charm. There’s a pleasant stretch of golden sand, and just a short walk or boat ride away you’ll find the peaceful seclusion of Pirate’s Bay – a beach so idyllic it starred in the 1952 movie version of Robinson Crusoe.

The white peaks of the Lefka Ori mountain range create a dramatic backdrop for Crete’s former capital of Chania. This city’s rich cultural heritage showcases everything from Byzantine monasteries to medieval churches and Turkish baths. At the heart of its enchanting Old Town you’ll find the Venetian harbor, with its landmark lighthouse and colorful waterfront palazzos. Behind that you’ll discover a maze of alleyways lined with fascinating cafés, galleries, bars and restaurants.