Small enough to be traversed easily on foot, Trogir sits on a tiny island off the Dalmatian Coast, connected by bridges to both the mainland and the neighboring island of Ciovo. Designated a UNESCO World Heritage site for its “beautiful Romanesque churches complemented by the outstanding Renaissance and Baroque buildings from the Venetian period,” this diminutive medieval town holds an abundance of appeal. One of the many impressive sights of Trogir, the 13th-century Cathedral of Saint Lawrence houses the Renaissance Chapel of Saint John and offers sweeping views from its bell tower.

Some may recognize Skiathos as a setting in the movie Mamma Mia! — which gives you an idea of how scenic this island is. The coastline is home to some of Greece’s most beautiful beaches, and that says a lot given this is the Greek Isles. Only accessible by boat, Lalaria is a favorite because of the soaring white cliffs that rise from the pebbly sands and the striking rock formations jutting into the sea. Koukounaries provides a contrast with silky sands, a backdrop of emerald pines and plenty of loungers and umbrellas.

A study in contrasts, the Greek island of Syros is as historic as it is modern, as Catholic as Orthodox, and as stately and traditional as it is hip and cosmopolitan. The capital of the Cyclades, the island is known for its own intriguing capital, the thriving port city of Ermoupoli. Ermoupoli is crowned by the bright blue dome of the Orthodox church and paved with marble flagstones that line the main square.

Italy’s easternmost city, Otranto sits just under the heel of the country’s boot, peering out at Albania across the Otranto Strait that separates the Adriatic and Ionian seas. Otranto’s walled Old Town has been recognized by UNESCO for historic sites such as the Aragonese Castle, which has rotating exhibits on the inside and dramatic views of the sea on the outside. Equally impressive is the Church of Saint Peter, with its Byzantine frescoes and architecture, and the Otranto Cathedral, with its rose window and an incomparable mosaic floor.

In the arch of Italy’s boot, tucked between the Mare Grande (Big Sea) and Mare Piccolo (Little Sea), sits the coastal city of Taranto. Founded by Spartans in the 8th century BC, the “City of Two Seas” is also a city of two faces with two bridges – Ponte Girevole and Ponte di San Francesco di Paola – separating the old town from the new. Legend has it that upon arrival at Taranto, Poseidon’s son saw a dolphin jumping out of the sea and took the encounter as a sign from his father that here was the place to build a town.