Under Sail from Sicily to the Greek Islands

Palermo is the Mediterranean's most intoxicating crossroads of civilisations — Arab arches meet Byzantine gold mosaics beneath Norman royal chapels in the extraordinary Palatine Chapel, a monument to 12th-century multicultural brilliance that is Sicily's single greatest work of art. The Ballarò and Capo street markets, among southern Italy's most atmospheric, tumble through the ancient city in a sensory barrage of swordfish, blood oranges, jasmine, and street food improvised across centuries. Do not leave without tasting arancini and sfincione, Sicily's gloriously thick street pizza. Spring (April–May) and autumn (September–October) offer the ideal climate — warm enough for the sea, cool enough for extended walking.

Reggio di Calabria is the toe of Italy's boot, home to the magnificent Bronzi di Riace bronze warriors and a sun-drenched waterfront promenade overlooking the Strait of Messina and Sicily. Must-dos include visiting the Magna Grecia museum, tasting 'nduja and grilled swordfish, and walking the Lungomare with Mount Etna in view. May through October offers the warmest weather and calmest strait conditions.

Taormina is a cliffside Sicilian jewel 200 meters above the Ionian Sea, featuring an ancient Greek theater with Mount Etna as its backdrop, the exquisite Isola Bella bay, and some of Sicily's finest cuisine. Must-dos include a performance at the Teatro Antico, the cable car to Isola Bella, and tasting Etna volcanic wines. April through June and September through October offer ideal temperatures.

Fiskardo is the only village on Kefalonia to survive the 1953 earthquake, preserving a stunning Venetian-era waterfront of pastel townhouses overlooking a harbor with views to Homer's Ithaca across the channel. Must-dos include dining on fresh fish at a harbor terrace, swimming at Emblisi Beach, and tasting local Robola wine. May through October offers ideal conditions, with September being especially pleasant.

Pylos, Greece is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Star Clippers. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is May through September, when mild temperatures and long days favor unhurried exploration.

Spetses is an aristocratic Saronic Gulf island renowned for its neoclassical mansions, car-free harbour, and heroic role in the Greek War of Independence under the legendary Bouboulina. Must-dos include visiting the Bouboulina Museum, swimming at Agioi Anargyroi beach, and lingering at the Dapia's waterfront cafés. May through October offers perfect conditions, with the September Armata festival providing a spectacular historical reenactment.

Lavrion, a historic port town in southeastern Attica, Greece, is famed for its ancient silver mines and vibrant maritime culture. Must-do experiences include indulging in grilled octopus at local tavernas and exploring nearby islands like Delos and Symi. The best time to visit is during the spring and early fall when the weather is pleasant, and the crowds are fewer.