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 1 of 4

Tamurel

Tamurel

Crewed

10 berths3 cabins27 m2004
from
€36,000
View →
Seven

Seven

Crewed

2 cabins15 m2008
from
€3,400
View →
Talitha

Talitha

Bareboat

10 berths4 cabins12 m2021
from
€3,440
View →
Paola

Paola

Bareboat

10 berths4 cabins12 m2019
from
€3,620
View →
Ginevra

Ginevra

Bareboat

10 berths4 cabins12 m2019
from
€3,620
View →
Blitz

Blitz

Bareboat

9 berths4 cabins13 m2022
from
€4,500
View →
Maria Elena

Maria Elena

Bareboat

10 berths4 cabins13 m2020
from
€4,210
View →
Patrizia

Patrizia

Bareboat

10 berths4 cabins13 m2020
from
€4,210
View →
Skyfall

Skyfall

Bareboat

9 berths4 cabins14 m2024
from
€5,500
View →
Enea

Enea

Bareboat

12 berths5 cabins14 m2024
from
€5,500
View →
Endeavour

Endeavour

Bareboat

11 berths5 cabins14 m2025
from
€6,200
View →
Antigone

Antigone

Bareboat

13 berths6 cabins15 m2024
from
€6,330
View →
Libera

Libera

Crewed

14 berths6 cabins16 m2026
from
€15,900
View →
Sikelia

Sikelia

Crewed

8 berths4 cabins17 m2020
from
€13,000
View →
Elena

Elena

Crewed

8 berths4 cabins17 m2020
from
€13,000
View →
Alfa.bm2

Alfa.bm2

Crewed

12 berths5 cabins17 m2023
from
€10,400
View →
Agad

Agad

Bareboat

9 berths4 cabins12 m2023
from
€3,800
View →
Silvia B

Silvia B

Bareboat

10 berths4 cabins12 m2021
from
€3,440
View →
Perrito Caliente

Perrito Caliente

Bareboat

10 berths4 cabins12 m2022
from
€4,000
View →
Fiamma

Fiamma

Bareboat

8 berths3 cabins11 m2018
from
€1,760
View →
Marina

Marina

Bareboat

7 berths3 cabins12 m2018
from
€2,250
View →
Vittoria

Vittoria

Bareboat

7 berths3 cabins12 m2018
from
€2,250
View →
Maria Louise II

Maria Louise II

Bareboat

9 berths4 cabins15 m1998
from
€4,800
View →
Ansimaste

Ansimaste

Crewed

10 berths2 cabins12 m2022
from
€2,900
View →
San Miguel

San Miguel

Bareboat

10 m2009
from
€2,900
View →
Expensive Toy

Expensive Toy

Bareboat

4 berths2 cabins10 m2015
from
€1,550
View →
Happy Planet

Happy Planet

Bareboat

6 berths2 cabins11 m2018
from
€1,200
View →
Joy Planet

Joy Planet

Bareboat

6 berths2 cabins11 m2020
from
€1,500
View →
Smile Planet

Smile Planet

Bareboat

6 berths2 cabins11 m2022
from
€1,500
View →
Zazu

Zazu

Bareboat

4 berths2 cabins11 m2025
from
€1,950
View →
Iulo

Iulo

Bareboat

4 berths2 cabins11 m2024
from
€1,750
View →
Nala

Nala

Bareboat

6 berths3 cabins11 m2025
from
€2,050
View →
Notus

Notus

Bareboat

8 berths3 cabins11 m2016
from
€1,900
View →
Shira

Shira

Bareboat

8 berths3 cabins11 m2018
from
€1,900
View →
Avajava

Avajava

Bareboat

6 berths3 cabins12 m2021
from
€2,000
View →
Arya

Arya

Bareboat

8 berths3 cabins12 m2022
from
€2,350
View →
Friend Planet

Friend Planet

Bareboat

8 berths3 cabins12 m2019
from
€1,880
View →
Sympathy Planet

Sympathy Planet

Bareboat

7 berths3 cabins12 m2021
from
€1,880
View →
Inycum

Inycum

Bareboat

8 berths3 cabins12 m2019
from
€2,100
View →
Palmarola

Palmarola

Bareboat

8 berths3 cabins12 m2022
from
€2,200
View →
Hedone

Hedone

Bareboat

8 berths3 cabins13 m2020
from
€2,400
View →
Simba

Simba

Bareboat

8 berths3 cabins13 m2025
from
€3,100
View →
Cassiopea

Cassiopea

Bareboat

8 berths3 cabins13 m2025
from
€2,850
View →
Ifigenia

Ifigenia

Bareboat

8 berths3 cabins13 m2026
from
€2,950
View →
Alicla

Alicla

Bareboat

8 berths3 cabins13 m2026
from
€2,650
View →
Ninive

Ninive

Bareboat

10 berths4 cabins13 m2026
from
€2,410
View →
Bloody Mary

Bloody Mary

Bareboat

8 berths3 cabins13 m2021
from
€1,760
View →
Si Puo Fare

Si Puo Fare

Bareboat

8 berths3 cabins13 m2023
from
€2,250
View →

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.