Sicily

Stayinto · Boat charter· Andalusia

Sicily

482 boats to choose fromDeparting from 22 ports

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

Select your departure date.

The fleet

The boats

482 boats available · 24 of 482 shown

Kali II - Luxury Aeolian ExperienceCatamaran

Kali II - Luxury Aeolian Experience

StayintoStayintoStayintoStayinto
4 cabins8 guestsCapo d'Orlando Marina
SikeliaCatamaran

Sikelia

StayintoStayintoStayintoStayinto
4 cabins11 guestsCapo d'Orlando Marina

From 11,485 € / week

PremiumCatamaran

Premium

StayintoStayintoStayinto
6 cabins13 guestsPorto di Castellammare del Golfo

From 4,514 € / week

Sunsail 404 ClassicCatamaran

Sunsail 404 Classic

StayintoStayintoStayinto
4 cabins8 guestsMarina Portorosa

From 3,674 € / week

Premium +Catamaran

Premium +

StayintoStayintoStayintoStayinto
4 cabins8 guestsTrapani

From 12,422 € / week

Harmony PlanetCatamaran

Harmony Planet

StayintoStayintoStayinto
6 cabins12 guestsMarina Portorosa

From 2,591 € / week

ElenaCatamaran

Elena

StayintoStayintoStayintoStayinto
4 cabins11 guestsCapo d'Orlando Marina

From 9,262 € / week

SAILUXE - AuraCatamaran

SAILUXE - Aura

StayintoStayintoStayintoStayinto
5 cabins10 guestsPorto di Castellammare del Golfo

From 27,641 € / week

SAILUXE - AuraCatamaran

SAILUXE - Aura

StayintoStayintoStayintoStayinto
5 cabins10 guestsCapo d'Orlando Marina

From 27,641 € / week

SAILUXE - La ControraCatamaran

SAILUXE - La Controra

StayintoStayintoStayintoStayinto
5 cabins10 guestsCapo d'Orlando Marina

From 27,641 € / week

SAILUXE - GloriaCatamaran

SAILUXE - Gloria

StayintoStayintoStayintoStayinto
5 cabins11 guestsCapo d'Orlando Marina

From 27,427 € / week

PremiumCatamaran

Premium

StayintoStayintoStayintoStayinto
4 cabins9 guestsTrapani

From 3,852 € / week

Oblivion PlanetCatamaran

Oblivion Planet

StayintoStayintoStayintoStayinto
6 cabins14 guestsLa Cala (Porto Palermo)

From 3,862 € / week

Fico - Premium lineCatamaran

Fico - Premium line

StayintoStayintoStayintoStayinto
4 cabins10 guestsMarina Portorosa

From 6,240 € / week

Sunsail 46 Cat ClassicCatamaran

Sunsail 46 Cat Classic

StayintoStayintoStayinto
4 cabins8 guestsMarina Portorosa

From 5,864 € / week

JovyCatamaran

Jovy

StayintoStayintoStayinto
4 cabins10 guestsCapo d'Orlando Marina

From 6,587 € / week

Flotrimaran

Flo

StayintoStayintoStayinto
3 cabins6 guestsTrapani

From 6,741 € / week

StronghyleCatamaran

Stronghyle

StayintoStayintoStayintoStayinto
5 cabins11 guestsMarina Villa Igiea

From 9,016 € / week

BeniMotorboat

Beni

StayintoStayintoStayinto
2 cabins6 guestsPorto di Giardini

From 24,074 € / week

Sunsail 52.4 ClassicSailboat

Sunsail 52.4 Classic

StayintoStayintoStayinto
5 cabins12 guestsMarina Portorosa

From 3,741 € / week

Blue MoonCatamaran

Blue Moon

StayintoStayintoStayinto
4 cabins10 guestsCapo d'Orlando Marina

From 4,612 € / week

Sun Odyssey 490 ClassicSailboat

Sun Odyssey 490 Classic

StayintoStayintoStayinto
5 cabins10 guestsMarina Portorosa

From 3,741 € / week

SAILUXE - FichettoCatamaran

SAILUXE - Fichetto

StayintoStayintoStayinto
4 cabins8 guestsPorto di Castellammare del Golfo

From 6,454 € / week

SAILUXE - GloriaCatamaran

SAILUXE - Gloria

StayintoStayintoStayintoStayinto
5 cabins11 guestsPorto di Castellammare del Golfo

From 27,427 € / week

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.

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