A patchwork of vineyards and olive groves, dotted with whitewashed hill towns and sun-bronzed beaches—Italy’s southern heel has no shortage of photogenic landscapes. There are a few surprises, too, including the baroque city of Lecce and the Itria Valley, with its UNESCO-listed trulli houses.

The capital of Puglia and one of southern Italy’s most prominent cities, Bari combines seaside charm and historical appeal. A major Mediterranean cruise port, the university city is also known for its old town, which boasts churches, picturesque courtyards, and other tucked-away gems.

A Puglia port town that’s equal parts historic and functional, Monopoli makes a splash with medieval churches and castles jutting above the Adriatic. It’s also a painter’s dream, with bright blue fishing boats adding a pop of colour against whitewashed harbour walls.

One of Puglia’s most picturesque enclaves, Ostuni is known as the White City thanks to its plenitude of white-washed houses. A quick trip from the coast, the city is also celebrated for its labyrinthine streets, cathedral, and ancient defensive walls.

Step back in time and imagine Italy as it was during 550 B.C. At least, that’s what you can do when you visit The Cilento—home to the remains of two ancient Greek cities: Paestum and Velia. To experience life a little later on, head to the Certosa di Padula, a Carthusian monastery (and World Heritage site) that dates back to 1306 and is known for its Baroque-style architecture. The park’s landscape also hints at these forgotten times with its vast seaside views and deep cave systems such as the Grotte di Castelcivita.

The strangers on Alfred Hitchcock's most famous train began their journey at Danbury, Connecticut's main station, along with thousands of other travelers over time. Now converted into the Danbury Railway Museum, the station and yards are open to visitors, with a collection of historic railroad cars and equipment. Just a few miles outside of the city's pretty historic center is Bear Mountain Reservation, a quiet forest parkland with hiking trails overlooking the calm waters of Candlewood Lake.

A short ride away from New York City on the Metro North commuter rail, Poughkeepsie sits on the banks of the Hudson River. The close proximity of Vassar College and the Culinary Institute of America guarantees the presence of fun boutiques and fine dining. Main Mall Row, a group of 1870s Renaissance Revival storefronts along Poughkeepsie's Main Street is on the National Register of Historic Places. The twenty-two surrounding parks provide the opportunity to take a relaxing break from city life.