Top Sicily Trips & Tours in September 2025

Spend 9 days on this small group journey through the treasures 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.

Embark on an 8-day "Longing for La Dolce Vita" cruise aboard the Sea Cloud Spirit. Begin in Taormina, a town known for its blend of cultures and varied cuisine. Explore Palermo and discover its historic palazzi and gold mosaics, then head to Lipari, an island with volcanic landscapes and a lively harbor town. The trip concludes in Amalfi.

Set sail on an 8-day cruise aboard the Royal Clipper, exploring Italy and Sicily with stops in Civitavecchia, Sorrento, Amalfi, Taormina, and Syracuse. Enjoy volcanic views at the Aeolian Islands and optional excursions to Pompeii while experiencing Mediterranean beauty and history.

Set sail on a 7-day cruise from Civitavecchia aboard the Royal Clipper, discovering Italy's stunning coastal towns and historic sites. Explore Sorrento, Amalfi, Taormina, and the Aeolian Islands, all while enjoying breathtaking landscapes and local charm.

Board the Star Flyer on this unforgettable 7-day cruise of the Mediterranean. Admire the perfect architecture and magical landscapes this region is famous for, visiting Ponza, Amalfi, Lipari, and more! Explore the Sistine Chapel and wander through the town of Pontine Islands.

Embark on an 8-day cruise in Venice and end in Valletta aboard L'Austral, exploring Ionian and Adriatic treasures. Enjoy excursions and French lectures and visit Malta, Montenegro, Croatia, and Italy for the 4th Opera Festival.

Embark on a 21-day cruise aboard the Royal Clipper from Rome to Lisbon, exploring stunning cities like the Amalfi Coast, Sicily, and the Balearic Islands. Enjoy optional excursions to historic sites while relaxing onboard with sailing and adventure activities amidst breathtaking landscapes.

Embark on an 11-day Adriatic adventure aboard World Navigator. Discover the historic charm of Venice, the stunning beaches of Zadar, and the medieval beauty of Kotor. Enjoy rich cultural experiences, breathtaking landscapes, and delectable cuisine throughout this unforgettable journey.

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.