Top Sicily Trips & Tours in May 2026

Spend 9 days on this small group journey through the highlights of Sicily to step into a world where ancient ruins stand alongside vibrant cities and picturesque landscapes. Discover ancient ruins, bask in the island's natural beauty, and indulge in Sicily's culinary delights.

During this 9-day cruise around Sicily aboard the new luxury expedition ship Le Bougainville, you'll be able to explore mythical places at the crossroads of Eastern and Western civilizations. Discover Sicily's most beautiful historic cities and ancient sites.

Embark on a 10-day Ancient Shores of Sicily and Malta cruise, aboard Sea Cloud II. Explore ancient cities, UNESCO-listed temples, and landscapes shaped by the Romans, Greeks, and Carthaginians. Visit Agrigento’s Valley of the Temples, the Ggantija Temples, and Valletta, stroll medieval Erice, and tour The Godfather’s Castello degli Schiavi.

Explore the heart of the Mediterranean on this 8-day Mediterranean Island Cruise with Smithsonian Journeys from Valletta to Nice aboard Le Bougainville. Discover Sicily, Sardinia, Corsica, and Elba's historical civilizations that left mark on these islands' language, cuisine, art, and architecture.

Set sail on a 10-day cruise from Malaga to Valletta aboard Le Boreal and explore UNESCO World Heritage Sites, ancient ruins, and vibrant local markets. Discover Roman theaters, Moorish palaces, Arab-Norman cathedrals, and Mediterranean coastlines. Enjoy cultural depth and historic architecture in each port.

Embark on a 7-day cruise aboard the Star Clipper, starting from Civitavecchia and visiting Italy's beautiful coastal spots like the Aeolian Islands and Amalfi. Conclude your journey with easy access to explore Rome.

Experience an 8-day Mediterranean sailing adventure from Civitavecchia, exploring Sicily, the Amalfi Coast, and the Aeolian and Pontine Islands aboard Star Clipper. Sail past Stromboli’s active volcano, wander historic Messina, and admire the coastal beauty of Amalfi and Sorrento. Explore Ponza’s unspoiled charm before returning to Rome’s port.

Embark on a 13-day Mediterranean Wonders Cruise from Spain to Greece aboard National Geographic Orion, explore ancient ruins, medieval towns, and local cuisine. Visit Menorca’s prehistoric stones, Bonifacio’s citadel, Sardinia’s artisan villages, savor Sicilian wine, swim in Kefalonia’s waters, and explore Delphi.

Set sail for a 10-day Mediterranean cruise from Valletta, Malta, to Civitavecchia, Italy, on the Emerald Sakara. Visit Sicilian beaches, Amalfi's historic sites, and enjoy stunning views from Capri and Sorrento, balancing relaxation with exploration.

Set sail on a 12-day cruise from Civitavecchia to Venice on the Star Clipper, exploring Italy and Croatia's hidden gems like Ponza and Otranto. Experience historic towns and local cuisine, and enjoy onboard relaxation and adventure across beautiful coastal seas.

Experience the nature and culture of the Aeolian Archipelago on this 8-day tour. Visit Lipari, Vulcano, Panarea, Stromboli, Filicidu, and Salina, which form one of the most active geological structures in the Mediterranean. Explore these beautiful coastal towns, visiting incredible volcanic rock formations and seafront black sand beaches.