Ancona in Le Marche is often overlooked as a mere jumping-off point for more glamorous European destinations. But there's an undeniable charm to this harborfront city, which was founded by ancient Greek settlers from Syracuse and maintains an identity characterized by a rich, layered history. Just meters from the port, you'll find lively piazzas, ancient architecture, and bustling trattorias serving up bowls of hearty brodetto, the city's famous fish stew. Journey through time, from the Paleolithic Period to the Middle Ages, at the fascinating Museo Archeologico Nazionale delle Marche, housed in the elaborately frescoed 16th-century Palazzo Feretti. From the old town, a stroll up Guasco Hill leads to the majestic Cattedrale di San Ciriaco, a Roman-Gothic basilica built atop the remains of an ancient temple dedicated to Aphrodite, where sweeping views stretch across the city and out over the riviera.

Embark on a cultural journey to the picturesque island of Korcula, a Croatian treasure surrounded by shimmering turquoise waters. As one of the oldest settlements in Croatia, the island dates back to ancient Greece and was once a hub for medieval trade. Stroll through the well-preserved medieval town, with its narrow cobbled streets, and uncover remnants of Roman rule and Illyrian settlements. Marvel at the grand Gothic-Renaissance architecture of St. Mark's Cathedral and the 15th-century walls that once guarded the city, and soak the vibrant cultural pulse, from traditional folk music and dance, to savory seafood cuisine and lively festivals.

From its origins as a Messapian settlement to its role as a strategic center of Roman naval power, and later as a passageway for pilgrims journeying to the Holy Land, the ancient Puglian city of Brindisi has always been a pivotal portal to other places. But this under-the-radar coastal treasure has plenty to offer of its own. Wander along its palm-lined seafront and weave your way through narrow streets to discover the quiet charm of a city steeped in history. Roman and medieval ruins pepper the center: look out for the Roman Columns, so significant to the city that they appear on its coat of arms; the Area Archeologica di San Pietro degli Schiavoni, which showcases remains of ancient houses, mosaic floors, and thermal baths; and the 12th-century Tempio di San Giovanni al Sepolcro, with its fantastic frescoes and lush gardens.

Immerse yourself in this immaculately preserved island covered in cypress and olive trees. Corfu is considered one of the Mediterranean's best kept secrets and its elegant downtown area, serene beaches and warm breezes will keep leave you truly captivated.

Today, its Old Town is alive with contemporary shops and traditional bazaars that teem with locals and visitors, surrounded by lively cafés. But this charming “old” quarter is infantile compared to one of Bodrum's most important sites: the Mausoleum of Halicarnassus. Dating back to 350 B.C., the 140-foot white marble structure still captivates even the savviest scientists, ranking as one of the Seven Wonders of the Ancient World.

Syros may lack the glitz of Mykonos and the Instagram appeal of Santorini, but this unsung Cyclades gem stands proudly apart from its neighbors with an identity all its own. Steeped in a rich Venetian heritage, the island offers a lesson in architectural diversity: its bougainvillea-lined streets showcase a mélange of grand neoclassical mansions, traditional whitewashed houses, Greek Orthodox churches, and Roman Catholic cathedrals. The pace is unhurried and easy-going: tavernas and bars are buzzy but never overrun – so you can linger over your meal and order another ouzo – and there's plenty of space on the sandy shores to spread your towel, even in peak season.