Southern Dalmatia's largest island, Korčula is quietly emerging as the most sophisticated and alluring island in the region. First settled by the ancient Greeks around 4 B.C. —who named it Kerkyra Melaina, or "Black Corfu," for its dark Aleppo pine trees—it spent several periods under Venetian rule between the 10th and 18th centuries, much to the frustration of Dubrovnik, which considered the Italian city-state its archrival. Venetian influence can still be seen in Korčula Town, one of the best preserved medieval island towns in the Mediterranean. It resembles a mini-Dubrovnik with its high fortified walls and circular fortresses jutting out into a sparkling sea; the main difference lies in the design of the streets, which are laid out in a fishbone pattern to prevent cold winter winds from whistling unimpeded through town. Within you'll find a treasure trove of Gothic and Renaissance churches, palaces, and piazzas, all built from fine local stone. Today Korčula Town is known for its traditional sword dances, and its main, though disputed, claim to fame as the birthplace of Marco Polo.
Beyond the capital, the island is made up of stone villages, miles of mountainous roads perfect for biking, secluded beaches, boutique wine, honey and olive oil producers, and proud, welcoming locals. Just 4 km (2½ miles) above Korčula Town you'll find Žrnovo, with its sleepy hamlets and walking trails past centuries-old cypresses, vineyards, and stone houses, plus some of the most traditional restaurants in the area. Lumbarda, 6 km (4 miles) southeast of Korčula Town with around 1,000 inhabitants, is where you'll find the nearest family-friendly sandy beaches and a handful of family wineries producing white wine from the indigenous grape Grk. The other main wine producing centers of Čara and Smokvica are inland, as is the smallest and oldest settlement on the island, picturesque Pupnat. To the west is the port town of Vela Luka, where you'll find beautiful beaches, and lovely Proizd, one of the many islets of the Korčula Archipelago.