Sailaway Charters
Sicily, Italy sailing area

Sicily · Italy

Sail Sicily.

Charter from Sicily, Portorosa, Capo D'orlando Marina, Palermo, Marina di La Cala, Marsala, Palermo, Marina Si.Ti.mar, Marina Poseidon, Milazzo, Sicily, Riposto, San Vito Lo Capo, Palermo, Siracusa, Sicily, Porto Xiphonio Augusta Marina, Porto Empedocle, Sicily and Trapani — 151 yachts on the dock right now.

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151 yachts132 bareboat

Why sail Sicily

Sicily gives you two very different weeks depending on where you cast off. From the north coast you reach the Aeolian Islands — seven volcanic islands, one of them (Stromboli) still throwing sparks after dark. From the west you have the Egadi and the shallow, wind-raked stretch past Marsala and Trapani. From the south-east there's the Baroque coast: Siracusa, Ortigia's stone quays, and quieter anchorages that most charter fleets never reach.

It's a working island, not a resort. You anchor off villages where the fishing boats still go out at 5am, tie up in harbours that smell of diesel and grilled sardines, and eat where the menu is whatever came in that morning. Good for sailors who want distance and variety in a week; less good if you want flat water and short hops the whole time.

Live fleet

Yachts available in Sicily.

151 yachts · page 4 of 4

Sicily questions

Asked and answered.

How much does a yacht charter in Sicily cost?
A week's bareboat monohull around 40–45ft runs a few thousand euros in June or September and more in July and August; catamarans and larger yachts cost more, and crewed charters add skipper and provisioning. On top of the base rate budget for fuel, marina fees, the end-of-charter clean and a refundable deposit. Send us your dates and crew size on WhatsApp for a firm quote — price on request.
Do I need a licence to charter bareboat in Sicily?
Yes. For bareboat you'll normally need an ICC or an equivalent national sailing qualification plus a VHF certificate, and some genuine Med experience helps because the passages to the Aeolians are open-water legs. If you don't hold a licence or would rather not skipper the crossings yourself, take a crewed charter with a skipper aboard. Message us with your certificates and we'll confirm what's accepted.
When is the best time to sail Sicily?
June and September are the sweet spot — warm water, settled weather and far fewer boats than peak. July and August are hot and busy, with popular anchorages filling by mid-afternoon. May and October are quieter and cheaper but weather is less reliable. Watch the maestrale, a north-westerly that can make the north coast and the Aeolian crossing lumpy, and the hot scirocco off Africa.
Where should I start a Sicily charter?
For the classic Aeolian island loop, start at Portorosa, Milazzo or Capo d'Orlando on the north coast — you're 20nm from Vulcano and Lipari. For the Egadi Islands and quieter western water, start Trapani or Marsala. For the Baroque south-east and Siracusa's Ortigia, base at Riposto, Augusta or Siracusa. Tell us on WhatsApp what you want to see and we'll match a base to it.
Is Sicily good for a family sailing holiday?
It can be, with the right plan. The Aeolians involve real open-water crossings, so a crewed charter or a settled shoulder-season week suits families better than a busy August bareboat. Lipari and Salina have good beaches, easy anchorages and towns for a night ashore. Choose short-hop days, avoid the exposed Stromboli anchorage in doubtful weather, and start early to claim a calm cove before the afternoon breeze fills.
Bareboat or crewed — which should I choose?
Choose bareboat if you hold the right licence, have Med experience and are happy planning the open crossings to the Aeolians yourself. Choose crewed if you're new to the area, sailing with family, or would rather leave the navigation and the weather calls to someone who knows which cove stays flat when the maestrale fills. Both monohulls and catamarans are available on either basis.
How many yachts can I charter in Sicily?
Right now there are 151 active yachts in Sicily, based out of Sicily, Portorosa, Capo D'orlando Marina, Palermo, Marina di La Cala, Marsala, Palermo, Marina Si.Ti.mar, Marina Poseidon, Milazzo, Sicily, Riposto, San Vito Lo Capo, Palermo, Siracusa, Sicily, Porto Xiphonio Augusta Marina, Porto Empedocle, Sicily and Trapani. The fleet list above is live from our operator system.
Bareboat or crewed in Sicily?
132 of the boats here are bareboat, 19 come crewed. Tell us your experience level and we'll match you.
How do I get a quote?
Send us your dates, your group and roughly the boat you want. Same day, we reply with three real options, three prices and the honest trade-offs.

By the cabin

Cabin cruises in Sicily

Scheduled crewed cruises — book by the cabin and share the yacht with a small group.

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Tell us roughly when and where. We'll send three real boats, three prices, the trade-offs — usually within the hour.