Escapade between Greek islands and Italian treasures

For better or worse, it can be difficult to reach Patmos—for many travelers, this lack of access is definitely for the better, since the island retains the air of an unspoiled retreat. Rocky and barren, the small, 34-square-km (21-square-mi) island lies beyond the islands of Kalymnos and Leros, northwest of Kos. Here on a hillside is the Monastery of the Apocalypse, which enshrines the cave where St. John received the Revelation in AD 95. Scattered evidence of Mycenaean presence remains on Patmos, and walls of the classical period indicate the existence of a town near Skala. Most of the island's approximately 2,800 people live in three villages: Skala, medieval Chora, and the small rural settlement of Kambos. The island is popular among the faithful making pilgrimages to the monastery as well as with vacationing Athenians and a newly growing community of international trendsetters—designers, artists, poets, and “taste gurus” (to quote Vogue’s July 2011 write-up of the island)—who have bought homes in Chora. These stylemeisters followed in the footsteps of Alexandrian John Stefanidis and the English artist Teddy Millington-Drake who, in the early ’60s, set about creating what eventually became hailed as one of the most gorgeous island homes in the world. The word soon spread thanks to their many guests (who included Jacqueline Kennedy Onassis) but, happily, administrators have carefully contained development, and as a result, Patmos retains its charm and natural beauty—even in the busy month of August.

Kalè polis, meaning beautiful city, is the name ancient Greek mariners bestowed on Gallipoli, with good reason. Situated on a mound, the Old Town with its labyrinth of winding lanes, emerges from the Ionian Sea. It is connected to the mainland and modern Gallipoli via a 17th-century bridge. The area lies on the Salentina Peninsula in the extreme southeast end of Italy, commonly referred to as the heel of the boot. The Salento region was inhabited already in prehistoric times; later centuries were marked by Greek, Norman, Byzantine and Baroque cultures. It is a land of farms, castles, works of art, myths and legends. Many heroic battles were fought; fierce resistance was shown by Gallipoli’s citizens against numerous invaders that included Romans, Vandals, Swabians, Venetians, French and lastly the English in 1809. In addition to its tumultuous history and natural beauty, the city’s claim to fame rests in its art treasures, most notably, the Basilica of Sant’Agata with its majestic 17th-century façade. Inside, the church contains a rich and important art collection with numerous works by its great native son, Giovanni Andrea Coppola.

The medieval cliff-hanging town of Taormina is overrun with tourists, yet its natural beauty is still hard to dispute. The view of the sea and Mt. Etna from its jagged cactus-covered cliffs is as close to perfection as a panorama can get—especially on clear days, when the snowcapped volcano's white puffs of smoke rise against the blue sky. Writers have extolled Taormina's beauty almost since it was founded in the 6th century BC by Greeks from nearby Naxos; Goethe and D. H. Lawrence were among its well-known enthusiasts. The town's boutique-lined main streets get old pretty quickly, but the many hiking paths that wind through the beautiful hills surrounding Taormina promise a timeless alternative. A trip up to stunning Castelmola (whether on foot or by car) should also be on your itinerary.

The largest and most developed of the Aeolians, Lipari welcomes you with distinctive pastel-color houses. Fields of spiky agaves dot the northernmost tip of the island, Acquacalda, indented with pumice and obsidian quarries. In the west is San Calogero, where you can explore hot springs and mud baths. From the red-lava base of the island rises a plateau crowned with a 16th-century castle and a 17th-century cathedral.

Once the intellectual capital of southern Europe, Palermo has always been at the crossroads of civilization. Favorably situated on a crescent-shaped bay at the foot of Monte Pellegrino, it has attracted almost every culture touching the Mediterranean world. To Palermo's credit, it has absorbed these diverse cultures into a unique personality that is at once Arab and Christian, Byzantine and Roman, Norman and Italian. The city's heritage encompasses all of Sicily's varied ages, but its distinctive aspect is its Arab-Norman identity, an improbable marriage that, mixed in with Byzantine and Jewish elements, created some resplendent works of art. No less noteworthy than the architecture is Palermo's chaotic vitality, on display at some of Italy's most vibrant outdoor markets, public squares, street bazaars, and food vendors, and above all in its grand climax of Italy's most spectacular passeggiata (the leisurely social stroll along the principal thoroughfare).