
Stayinto · Boat charter· Andalusia
Sicily
Sicily, the Mediterranean's largest island, sits at the crossroads of European and North African cultures, offering sailors a distinctive blend of history, coastline, and maritime tradition. As part of Italy, with charter operations extending to Malta, this sailing area commands…
Sicily, the Mediterranean's largest island, sits at the crossroads of European and North African cultures, offering sailors a distinctive blend of history, coastline, and maritime tradition. As part of Italy, with charter operations extending to Malta, this sailing area commands a fleet of 482 yachts and 22 marinas, making it a well-established hub for bareboat and crewed charters. The region's ports range from working fishing villages to established nautical centres, each reflecting centuries of seafaring heritage.
Sailors navigating Sicilian waters encounter dramatic limestone cliffs, hidden anchorages, and strategic passages that have shaped Mediterranean trade routes for millennia. The sailing season benefits from consistent winds and relatively sheltered bays, while the surrounding coastline reveals Norman architecture, Greek temples, and Arab-Norman towns visible from the water. With 24 day-charter and activity experiences available, visitors can combine sailing with cultural exploration—whether anchoring near archaeological sites, visiting island communities, or engaging with local maritime practices.
The sailing area's infrastructure supports diverse itineraries, from circumnavigating the island itself to island-hopping toward the Aeolian Islands or crossing toward Malta. Marinas and anchorages accommodate different vessel sizes and preferences, while the region's culinary and cultural offerings extend beyond the water. For sailors seeking a Mediterranean destination with depth of character and reliable maritime facilities, Sicily presents both technical sailing interest and the opportunity to engage with one of Europe's most historically layered regions.
Pick your week
The fleet
The boats
482 boats available · 24 of 482 shown
Kali II - Luxury Aeolian Experience
Sikelia
From 11,485 € / week
Premium
From 4,514 € / week
Sunsail 404 Classic
From 3,674 € / week
Premium +
From 12,422 € / week
Harmony Planet
From 2,591 € / week
Elena
From 9,262 € / week
SAILUXE - Aura
From 27,641 € / week
SAILUXE - Aura
From 27,641 € / week
SAILUXE - La Controra
From 27,641 € / week
SAILUXE - Gloria
From 27,427 € / week
Premium
From 3,852 € / week
Oblivion Planet
From 3,862 € / week
Fico - Premium line
From 6,240 € / week
Sunsail 46 Cat Classic
From 5,864 € / week
Jovy
From 6,587 € / week
Flo
From 6,741 € / week
Stronghyle
From 9,016 € / week
Beni
From 24,074 € / week
Sunsail 52.4 Classic
From 3,741 € / week
Blue Moon
From 4,612 € / week
Sun Odyssey 490 Classic
From 3,741 € / week
SAILUXE - Fichetto
From 6,454 € / week
SAILUXE - Gloria
From 27,427 € / week
Ports map
22 departure ports in this area
Each marker is a marina where your charter can start.
- Marina Portorosa — 188 boats
- Capo d'Orlando Marina — 125 boats
- La Cala (Porto Palermo) — 43 boats
- Marsala Marina — 30 boats
- Marina Villa Igiea — 17 boats
- Poseidon Marina — 15 boats
- Trapani — 11 boats
- Porto di Castellammare del Golfo — 10 boats
- Porto di Tropea — 10 boats
- Marina Galizzi — 9 boats
- Porto Santa Maria Maggiore — 5 boats
- Vibo Marina — 5 boats
- Marina di Ragusa — 2 boats
- Marina Stella del Sud — 2 boats
- Porto di Giardini — 2 boats
- Riposto — 2 boats
- Lipari — 1 boat
- Marina Arenella — 1 boat
- Marina del Nettuno — 1 boat
- Presidiana Marina — 1 boat
- San Vito Lo Capo — 1 boat
- Siracusa — 1 boat
Ready to board in Sicily?
Set your dates and sailing style. Stayinto Concierge is available 7 days a week to confirm your charter.
Destination guide
Everything about Sicily
Overview
Sicily, the Mediterranean's largest island, sits at the crossroads of European and North African cultures, offering sailors a distinctive blend of history, coastline, and maritime tradition. As part of Italy, with charter operations extending to Malta, this sailing area commands a fleet of 482 yachts and 22 marinas, making it a well-established hub for bareboat and crewed charters. The region's ports range from working fishing villages to established nautical centres, each reflecting centuries of seafaring heritage.
Sailors navigating Sicilian waters encounter dramatic limestone cliffs, hidden anchorages, and strategic passages that have shaped Mediterranean trade routes for millennia. The sailing season benefits from consistent winds and relatively sheltered bays, while the surrounding coastline reveals Norman architecture, Greek temples, and Arab-Norman towns visible from the water. With 24 day-charter and activity experiences available, visitors can combine sailing with cultural exploration—whether anchoring near archaeological sites, visiting island communities, or engaging with local maritime practices.
The sailing area's infrastructure supports diverse itineraries, from circumnavigating the island itself to island-hopping toward the Aeolian Islands or crossing toward Malta. Marinas and anchorages accommodate different vessel sizes and preferences, while the region's culinary and cultural offerings extend beyond the water. For sailors seeking a Mediterranean destination with depth of character and reliable maritime facilities, Sicily presents both technical sailing interest and the opportunity to engage with one of Europe's most historically layered regions.