Itinerary Overview

A balance of sailing, savoring & exploring idyllic isles

Set sail aboard the majestic four-masted Sea Cloud on a journey into the culture, history, and cuisine of Sicily and Malta. Step into the past among cities and temples left behind by the Romans, Greeks, Carthaginians, and prehistoric peoples—to name just a few. From Taormina to Gozo, wander through charming towns where modern-day life thrives amid glorious vestiges of ancient civilizations, and challenge your conceptions of Italian cuisine as you taste Sicily’s take on pizza, pastries, and wine. We’ll visit no fewer than five UNESCO World Heritage Sites: Agrigento, Siracusa, the Aeolian Islands, the city of Valletta, Malta’s megalithic temples; and we’ll have views of a sixth, Mount Etna. Savor Sea Cloud’s elegant comfort during afternoons under billowing sails, and enjoy an incomparable Mediterranean adventure that harkens back to the golden age of ship travel.



  • Sail the shimmering waters of the Mediterranean, Tyrrhenian, and Ionian seas aboard the historic square-rigger Sea Cloud.
  • Explore enchanting piazzas and winding alleyways of picturesque towns from Lipari to Taormina and Ortigia in the company of local guides.
  • Visit an array of UNESCO World Heritage Sites, from Greco-Roman ruins in Siracusa and Agrigento to the ancient temples of Ġgantija.
  • Experience Sicily’s unique cuisine at a wine tasting in Marsala, in Erice’s renowned Pasticceria Maria Grammatico, and at a private lunch in a historic castle near Taormina.

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