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.

See yachts in SicilyTalk to an expert
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 2 of 4

Bloody Mary

Bloody Mary

Bareboat

8 berths3 cabins13 m2021
from
€2,100
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Akira

Akira

Bareboat

10 berths4 cabins13 m2022
from
€3,200
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Pepsi

Pepsi

Bareboat

10 berths4 cabins13 m2024
from
€3,200
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Ventotene

Ventotene

Bareboat

10 berths4 cabins13 m2024
from
€3,200
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Fiodena

Fiodena

Bareboat

10 berths4 cabins13 m2019
from
€2,950
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Amaco

Amaco

Bareboat

8 berths3 cabins14 m2025
from
€3,000
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Neptune Planet

Neptune Planet

Bareboat

10 berths4 cabins14 m2016
from
€2,080
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Fun Planet

Fun Planet

Bareboat

10 berths4 cabins14 m2017
from
€2,180
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Pinacolada

Pinacolada

Bareboat

10 berths4 cabins14 m2017
from
€1,680
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Summer Planet

Summer Planet

Bareboat

10 berths4 cabins14 m2019
from
€2,300
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Adventure Planet

Adventure Planet

Bareboat

10 berths4 cabins14 m2020
from
€2,380
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Wonder Planet

Wonder Planet

Bareboat

10 berths4 cabins14 m2020
from
€2,400
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Mania Planet

Mania Planet

Bareboat

10 berths4 cabins14 m2021
from
€2,500
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Discovery Planet

Discovery Planet

Bareboat

10 berths4 cabins14 m2021
from
€2,380
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Aquilo

Aquilo

Bareboat

10 berths4 cabins14 m2016
from
€3,200
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Diego

Diego

Bareboat

10 berths4 cabins14 m2018
from
€3,200
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Pinacolada

Pinacolada

Bareboat

10 berths4 cabins14 m2017
from
€2,200
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Valchiria

Valchiria

Bareboat

11 berths4 cabins15 m2022
from
€3,300
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Bedda Matri

Bedda Matri

Bareboat

11 berths4 cabins15 m2025
from
€4,150
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M'arricrio

M'arricrio

Bareboat

11 berths4 cabins15 m2023
from
€4,000
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Chuck

Chuck

Bareboat

11 berths4 cabins15 m2024
from
€3,500
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Grazia

Grazia

Bareboat

11 berths4 cabins15 m2023
from
€3,750
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Soft Touch

Soft Touch

Bareboat

8 berths4 cabins15 m2023
from
€3,800
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Clelia

Clelia

Bareboat

12 berths5 cabins15 m2024
from
€3,300
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Perla

Perla

Bareboat

12 berths5 cabins15 m2024
from
€3,300
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Kalypso

Kalypso

Bareboat

10 berths4 cabins15 m2025
from
€4,000
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Salima

Salima

Bareboat

11 berths4 cabins15 m2026
from
€4,500
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Paradise Planet

Paradise Planet

Bareboat

14 berths5 cabins15 m2020
from
€5,940
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Jovy

Jovy

Crewed

8 berths4 cabins15 m2021
from
€7,200
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Eden Planet

Eden Planet

Bareboat

13 berths5 cabins15 m2022
from
€5,940
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Oblivion Planet

Oblivion Planet

Bareboat

14 berths5 cabins15 m2023
from
€5,940
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Salazar

Salazar

Bareboat

14 berths5 cabins15 m2022
from
€7,000
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Holiday Planet

Holiday Planet

Bareboat

12 berths5 cabins15 m2019
from
€2,600
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Moscow Mule

Moscow Mule

Bareboat

12 berths5 cabins15 m2019
from
€2,000
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Dream Planet

Dream Planet

Bareboat

12 berths5 cabins15 m2020
from
€2,720
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Sunshine Planet

Sunshine Planet

Bareboat

12 berths5 cabins15 m2021
from
€2,720
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Sirius

Sirius

Bareboat

12 berths5 cabins15 m2019
from
€4,000
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Moscow Mule

Moscow Mule

Bareboat

12 berths5 cabins15 m2019
from
€3,000
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Albus

Albus

Bareboat

15 berths6 cabins16 m2021
from
€3,800
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Wish Planet

Wish Planet

Bareboat

13 berths5 cabins16 m2022
from
€3,810
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Atua

Atua

Bareboat

12 berths5 cabins16 m2023
from
€4,500
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Taddarita

Taddarita

Bareboat

13 berths5 cabins16 m2025
from
€5,250
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Euphoria Planet

Euphoria Planet

Bareboat

11 berths4 cabins17 m2022
from
€3,440
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Razzmatazz

Razzmatazz

Bareboat

12 berths4 cabins17 m2023
from
€5,500
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Carmen Federica

Carmen Federica

Bareboat

8 berths3 cabins17 m2020
from
€5,250
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Magic Planet

Magic Planet

Bareboat

11 berths4 cabins17 m2019
from
€3,310
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Paladino

Paladino

Crewed

6 berths3 cabins17 m2006
from
€25,000
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Angelica

Angelica

Crewed

10 berths4 cabins22 m2005
from
€38,000
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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.

Talk to a real charter expert

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.

Real humans on every channel — WhatsApp, email, phone. No call centre.

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.

60 seconds. No payment until you choose a boat.
Yacht under sail at sunset

Free quote

Get three real options.

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