2-Week Skippered Sailing Adventure from Trapani to Sicily’s Hidden Gems aboard Sun Odyssey 449

Embark on the ultimate Sicilian sailing experience with this extended 2-week skippered charter aboard the Sun Odyssey 449. Departing from Trapani, this immersive itinerary offers a rich blend of volcanic exploration, secluded beaches, vibrant marine life, and cultural heritage, as you visit remote island jewels including Pantelleria, Linosa, and Lampedusa, before returning through Marettimo, Favignana, and Levanzo.

Day 1 (Saturday): Step aboard your yacht in Trapani at 18:00. Following a warm welcome and safety briefing, explore the city’s baroque heart before your first night aboard.

Day 2 (Sunday): A long 74 NM sail brings you to Pantelleria, Sicily’s “Black Pearl.” Upon arrival, unwind amidst volcanic vistas and soak in the thermal waters of the island’s natural hot springs.

Day 3 (Monday): Delve deeper into Pantelleria. Visit Specchio di Venere, hike Montagna Grande, and sip local wines at vineyard estates. Sunset at Balata dei Turchi caps the day beautifully.

Day 4 (Tuesday): Depart early for Linosa (68 NM). Arrive to a unique island of pastel homes and protected marine areas. Walk its colorful lanes, observe sea turtles, and savor island hospitality.

Day 5 (Wednesday): A short hop brings you to Lampedusa (24 NM), where Rabbit Beach awaits with fine white sands and turquoise waters. Spend the day snorkeling and absorbing the island’s raw Mediterranean beauty.

Day 6 (Thursday): Explore Lampedusa via boat tour, dive sites, and hidden coves. Visit Cala Croce for sunset drinks and local delicacies.

Day 7 (Friday): Spend a leisure day enjoying the island’s relaxed pace, then prepare for your return leg.

Day 8 (Saturday): Sail back to Pantelleria (78 NM). Enjoy a quiet evening reflecting on the adventure thus far, anchored in a calm harbor or strolling through town.

Day 9 (Sunday): A relaxed day to explore Pantelleria further or enjoy its thermal mud and scenic bike paths.

Day 10 (Monday): Set sail for Marettimo (65 NM), arriving late afternoon. Discover Punta Troia Castle and snorkel near sea caves before resting under starlit skies.

Day 11 (Tuesday): Dive into Marettimo’s nature. Enjoy guided walks, Roman ruins, and tranquil beach time.

Day 12 (Wednesday): Sail to Favignana (13 NM). Visit Cala Rossa, the Florio Tonnara Museum, and enjoy cycling around the island’s rustic trails.

Day 13 (Thursday): A leisure day on Favignana—snorkel, dive, or unwind on deck with Sicilian wine.

Day 14 (Friday): Final stops include Levanzo (3 NM) and the return to Trapani (20 NM). See Grotta del Genovese’s ancient cave art before sailing home for a farewell night in Trapani Marina.

Day 15 (Saturday): Disembark at 09:00, completing two weeks of unforgettable sailing and cultural adventure.

The Sun Odyssey 449 is crafted for long-distance comfort and reliability. Its 4-cabin, 2-bathroom configuration is perfect for extended charters, providing plenty of personal space and relaxation areas. Powered by a 57 HP Yanmar engine, it’s built for performance and ease, even on 12-14 hour sails.

The onboard experience is enhanced with amenities such as a bimini, electric windlass, fridge, boiler, GPS, and more. Its generous cockpit layout allows for smooth socializing and al fresco dining throughout the voyage.

This rare two-week sailing journey offers guests the opportunity to witness Sicily’s full island spectrum—volcanic wilderness, historic fishing villages, and glistening Mediterranean waters—all from the comfort of a premium yacht. It's the perfect escape for travelers craving depth, diversity, and immersive coastal experiences.