
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.
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.
The sailing areas
The Aeolians are the headline grounds. From Milazzo or Portorosa it's roughly 20nm to Vulcano and Lipari, then island-hopping north to Panarea, Salina, Stromboli, and the further-out Filicudi and Alicudi. Deep water, few hazards, dramatic backdrops. Anchorages can be exposed and roll-prone, so read the forecast before you commit to a night at anchor.
The Egadi Islands — Favignana, Levanzo, Marettimo — sit off Trapani and Marsala on the west coast. Clearer water, tuna history, quieter than the Aeolians in high season.
The south-east runs Siracusa, Augusta, down towards Porto Empedocle. Ortigia's marina puts you a two-minute walk from the old town. Longer passages, fewer boats.
Harbours and bases
Our Sicilian bases cluster on three coasts. On the north you've got Portorosa, Capo d'Orlando, and Milazzo (Marina Poseidon and Marina Si.Ti.mar) — the natural launch points for the Aeolians. Palermo (Marina di La Cala) sits mid-coast. On the west, Trapani and Marsala open the Egadi and San Vito Lo Capo. On the east and south-east, Riposto (under Etna), Augusta (Porto Xiphonio), Siracusa, and Porto Empedocle.
Most first charters start Portorosa or Milazzo for the Aeolian loop. Choose a west or south-east base if you've sailed here before and want emptier water.
Season and winds
The season runs roughly May to October. June and September are the sweet spot: warm water, settled weather, fewer boats than August. July and August are busy, hot, and the popular anchorages fill by mid-afternoon — arrive early or plan around it.
The dominant summer wind is the maestrale (mistral), a north-westerly that can build fast across the Tyrrhenian and make the north coast and the crossing to the Aeolians lumpy. The scirocco brings hot, hazy air off Africa and can kick up the south coast. Mornings are often light; the breeze fills in the afternoon. None of it is extreme in a normal summer week, but the Aeolian anchorages are open water — a wind shift overnight can turn a calm cove into a rolly one. Plan bailout harbours.
Charter types
You can charter here bareboat or crewed. Bareboat suits skippers with an ICC or equivalent and some Med experience — the grounds are forgiving but the passages to the Aeolians are proper open-water legs. Crewed charters put a skipper aboard who knows which anchorage stays flat when the maestrale fills; worth it for first-timers, families, or anyone who'd rather not navigate the crossing themselves. Monohulls and catamarans are both available; cats earn their keep here for the extra deck space and shallower draught around the Egadi shallows.
Realistic costs
A week's bareboat monohull in the 40–45ft range typically runs a few thousand euros in shoulder season and climbs in July/August; catamarans and larger yachts sit higher. Crewed charters add skipper and provisioning on top. Budget separately for fuel, marina fees (Ortigia and the popular Aeolian berths aren't cheap), the end-of-charter clean, and a security deposit. For a firm quote on specific dates and a specific yacht, Price on request — message us on WhatsApp with your week and crew size and we'll come back with real numbers, not a headline rate.
A sample week — the Aeolian loop
Day 1 — Board at Portorosa or Milazzo, provision, short shakedown sail, night in the marina.
Day 2 — Cross to Vulcano (~20nm). Anchor off the black-sand beach, walk up to the fumaroles if the smell doesn't put you off.
Day 3 — Short hop to Lipari. Town quay or anchor off; the biggest of the islands, good for reprovisioning and a proper dinner ashore.
Day 4 — Panarea — the prettiest and priciest of the group. Anchor off the islet of Basiluzzo or take a buoy.
Day 5 — Stromboli. Time it to be at anchor off the Sciara del Fuoco after dark and watch the volcano throw sparks. Exposed anchorage — check the forecast.
Day 6 — Salina — greener, quieter, malvasia wine and caper farms. Anchor at Santa Marina or Rinella.
Day 7 — Long leg back to Milazzo/Portorosa, or break it with a stop at Vulcano. Refuel, hand back the next morning.
Swap in Filicudi and Alicudi if you've a fast boat and settled weather; drop Panarea if the crowds aren't your thing.
Getting there
Fly into Catania (east) or Palermo (north-west) — both have wide European connections. Catania is closest to Riposto, Augusta and the south-east; Palermo serves the north coast and Trapani (Trapani also has its own smaller airport). From either airport it's a road transfer to base — an hour or more to Portorosa or Milazzo, less to the nearer marinas. Book transfers in advance in July and August. Turnaround is usually Saturday. Message us on WhatsApp before you book flights and we'll confirm the base, the handover time, and which airport actually saves you the drive.
Live fleet
Yachts available in Sicily.
151 yachts · page 4 of 4

Enrica
Bareboat

Erminia
Bareboat

Suami
Bareboat

Francoise
Bareboat

Teresa
Bareboat

Anita II
Crewed

Micus
Crewed
Sicily questions
Asked and answered.
How much does a yacht charter in Sicily cost?
Do I need a licence to charter bareboat in Sicily?
When is the best time to sail Sicily?
Where should I start a Sicily charter?
Is Sicily good for a family sailing holiday?
Bareboat or crewed — which should I choose?
How many yachts can I charter in Sicily?
Bareboat or crewed in Sicily?
How do I get a quote?
By the cabin
Cabin cruises in Sicily
Scheduled crewed cruises — book by the cabin and share the yacht with a small group.

Real people
Talk to a human
A real person reads every message and replies within 24 hours — no bots, no auto-replies.
- Honest advice from sailors, not salespeople
- We reply within 24 hours
- No spam, ever
Talk to an expert
Get three options.
Real sailors who run the trips — tell us your week, your group and your vibe. Same day, we send three boats, three prices and the honest trade-offs. Boats we would put our own families on.
Final boarding call
Why not you?
New sailors, beginners or seasoned skippers — tell us when, where and how many. We send three real options the same day. No spam, no fluff, no commitment.


