2-Week Skippered Sailing Adventure from Trapani to Sicily’s Hidden Gems - Sun Odyssey 349 Yacht

This extended 14-day skippered sailing charter is a grand exploration of Sicily’s southern and western maritime gems. From the wild thermal beauty of Pantelleria and the rare ecological sanctuaries of Linosa and Lampedusa to the storied Egadi Islands, this route is a slow-travel dream for explorers. With the agile Sun Odyssey 349 as your vessel, this voyage balances full-day offshore sails with relaxing anchorages, diving excursions, and cultural discovery — perfect for seasoned adventurers and newcomers to the Mediterranean alike.

Day 1: Welcome aboard at 18:00 in Trapani. After crew introductions and yacht orientation, guests can enjoy a Sicilian dinner in the historic center. Overnight at the marina sets a calm tone for the epic voyage ahead.

Day 2: Sail 74 NM to Pantelleria. Spend the day adjusting to the rhythm of life at sea as you cross open waters, arrive by late afternoon, and anchor near the island’s rocky coastline.

Day 3: Visit Specchio di Venere, hike Montagna Grande, and enjoy thermal mud baths. Discover dammusi homes and enjoy seafood with a view of Balata dei Turchi.

Day 4: Another long sail (68 NM) leads to Linosa. Explore the vibrant island streets, spot marine turtles, and dine under the stars on freshly grilled catch-of-the-day.

Day 5: Sail 24 NM to Lampedusa. Highlights include Rabbit Beach, snorkeling in marine sanctuaries, and coastal cave tours. Overnight in the calm harbor or secluded bay.

Day 6: A second day in Lampedusa invites deeper exploration — from diving excursions to lazy afternoons in Cala Croce.

Day 7: Enjoy a relaxed beach day before sailing 78 NM back to Pantelleria. Anchor in the quiet marina and enjoy local wine under the stars.

Day 8-9: These days offer downtime in Pantelleria — bike tours, winery visits, or leisurely onboard relaxation before preparing for the next leg.

Day 10: Long sail (65 NM) to Marettimo. Dive into island history with castle hikes and cave swims before anchoring in serenity.

Day 11-13: Continue exploring Marettimo, Favignana, and Levanzo. Swim in Cala Rossa, tour the Tuna Museum, and visit Grotta del Genovese.

Day 14: Final sail to Trapani. Celebrate your journey with dinner onboard or a farewell drink in town.

Day 15: Disembark at 09:00, closing a remarkable sailing expedition rich in nature, history, and sea.

The yacht’s adaptability and reliability are essential for a voyage of this scale. With 3 cabins, a 20 HP engine, a range of navigational equipment, and onboard amenities like a galley, electric fridge, cockpit table, and shower systems, the Sun Odyssey 349 makes extended cruising feel like home. Its efficient hull design and bimini provide both speed and protection across long passages.

This journey offers a deep and immersive connection to Sicily’s islands, combining rare destinations with everyday comfort. For those seeking an adventure that unfolds slowly and richly, this two-week odyssey is unmatched.