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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.

Located on Turkey’s sun-drenched Aegean coast, the town of Bodrum effortlessly blends seaside chic with ancient history and a relaxed beach scene. The town is the hub for boating on the peninsula, and traditional wooden gulet boats will take you along the coastline to idyllic hidden coves to swim in sparkling turquoise waters. Bodrum’s 15th century St. Peter’s Castle stands guard over the old bazaar district’s narrow cobbled streets, quaint cafés, artisan workshops and bougainvillea-draped whitewashed walls.

Sitting on a spectacular stretch of coastline on the ‘heel’ of Italy, Bari is Puglia’s bustling capital. The city’s historic Bari Vecchia district is a labyrinth of charming medieval streets where you’ll see local women selling homemade orecchiette pasta and the faithful making their pilgrimages to the 12th century Basilica San Nicola. Head out of town and explore fascinating heritage sites like Alberobello, a village of unique domed trulli structures; or relax on one of the many sandy beaches that sit beneath the region’s ancient clifftop villages.