Otranto, Italy

The easternmost town on the Italian mainland, Otranto enchants with its medieval architecture and relaxed beachfront atmosphere. As you approach the modest façade of the town’s 11th-century cathedral, admire the delicately carved rose window, a preview of the wonders found within, which include an extraordinary mosaic floor known as the Tree of Life. The imposing Castello Aragonese invites exploration both along the ramparts and in the dry moat, a perfect vantage point from which to admire the fort’s massive cylindrical towers.

Sun-lovers flock to the town’s beaches, which wrap around a protected cove lapped by gentle waves. While roaming the Old Town’s warren of narrow streets and cozy squares, you’ll discover enticing shops and eateries housed in age-old stone buildings. Later in the day, both residents and visitors congregate on the seaside promenade for their passeggiata, a typical Italian stroll that affords marvelous views of the sparkling sea. Stop at one of Otranto’s many excellent restaurants for a taste of orecchiette, which amusingly means small ear in Italian and is a popular regional pasta often served with savory ricotta.