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.

Life in the beautifully-preserved ‘Sailing Capital of the U.S.’ revolves around one thing: its rich maritime culture. Sitting at the heart of Chesapeake Bay – the largest estuary in the country – the charming state capital of Maryland is abuzz with seafaring glamour. From the countless boats that line its City Dock, to the U.S. Naval Academy students strolling through the cobblestoned streets in their starched white uniforms, maritime heritage is everywhere you look.