Bozcaada Island, Turkey

Experience an intriguing meld of Greece and Turkey on the island of Bozcaada, an often-overlooked stunner with a fascinating past. You’ll learn that according to mythology Achilles defeated a local king during the Trojan War, a dramatic harbinger of the island’s turbulent history under the rule of Greece, the Republics of Genoa and Venice, the Ottoman Empire and even Russia. As you weave along cobbled streets lined with whitewashed houses, pop into charming shops featuring handmade keepsakes and delicious marmalades, including a much-heralded tomato jam.

Hugging a rocky headland that extends into the sea, the 15th-century Bozcaada Castle stands as one of Turkey’s largest and best-preserved fortifications. While walking the crenellated parapets, you’ll enjoy wonderful views of the town and the surrounding vineyard-covered hills. Several superb wines are crafted on Bozcaada, including internationally acclaimed varietals from the Amadeus and Corvus vineyards, which you can sample at one of the town’s taverns. In the evening, relax at a welcoming seaside café and snack on tantalizing meze as the sun slowly sets behind the magnificent castle.