Map of Sicily

The next stage of our voyage takes us from the volcanic island of Vulcano on a spectacular anti-clockwise journey around Sicily, eventually arriving in the historic port city of Messina. This route unveils the island’s extraordinary diversity, from dramatic coastlines and ancient cities to golden beaches and sleepy fishing villages, all steeped in centuries of history and vibrant Mediterranean life.

Leaving behind the smoking peaks of Vulcano, we head southwest past Capo Calavà and make landfall along Sicily’s northern coast. Our first major stop is Cefalù, a postcard-perfect town nestled between sea and mountain. Its Norman cathedral, a UNESCO World Heritage Site, towers above cobbled streets and golden sands. Whether you anchor offshore or dock at the nearby marina, Cefalù invites you to explore its old-world charm, sample local granita, and enjoy a sunset aperitivo with a view of La Rocca towering behind you.

Continuing westward, the coastline becomes more rugged, eventually revealing the Gulf of Palermo. The capital city of Sicily, Palermo is a thrilling contrast of cultures, flavors, and architecture. Docking at the marina near the city center, sailors can step ashore to discover Byzantine mosaics, Baroque churches, and bustling street markets where Arab, Norman, and Italian influences collide in the local cuisine. It’s a city that rewards all the senses and makes for a rich, extended stopover.

From Palermo, we round the northwest tip of the island and make way for the Egadi Islands, a short detour well worth the time. These unspoiled isles, Favignana, Levanzo, and Marettimo, offer crystal-clear waters, caves, and quiet anchorages ideal for snorkeling and slowing the pace. Back on the Sicilian mainland, we sail past Trapani and head south toward Marsala and Mazara del Vallo, where North African influence meets traditional Sicilian life in the winding kasbah-style streets.

The southern coast of Sicily offers a more relaxed, sun-drenched vibe. Near Sciacca and Porto Empedocle, the beaches are wide and golden, and the anchorages peaceful. Inland, the ancient ruins of Agrigento and the Valley of the Temples remind us that Sicily has been a crossroads of civilizations for millennia. As we continue east, the towering outline of Mount Etna begins to rise inland, guiding our passage toward the Ionian coast.

Siracusa is a must-stop destination, one of the most powerful cities of the ancient world and still a place of timeless beauty. Mooring in the protected harbor near Ortigia, the city’s historic heart, you can wander past Greek temples, Baroque piazzas, and waterfront taverns. Just north lies Taormina, perched dramatically above the sea with its famous Greek theatre and stunning views over the Ionian coast. The nearby bays of Isola Bella and Mazzarò offer idyllic places to drop anchor and swim in turquoise waters.

As we near the end of our journey, the Strait of Messina comes into view. This legendary waterway, known for its swift currents and mythical sea monsters of old, marks our return to northeastern Sicily. The city of Messina welcomes us with its broad harbor, vibrant street life, and historical landmarks. It’s the perfect end point to a voyage that has taken us through the soul of Sicily, from fire and stone to art and flavor, from wind-swept islands to golden shores.

Sailing from Vulcano to Messina around Sicily offers a rare and enriching perspective of the island’s incredible variety. Every stretch of coast tells a different story, and every port brings new colors, tastes, and traditions. It’s a journey that captures the essence of the Mediterranean, wrapped in the warmth and wonder of Sicily itself.