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 3 of 4

Rossa

Rossa

Bareboat

8 berths4 cabins13 m2025
from
€4,060
View →
Harley Quinn

Harley Quinn

Bareboat

8 berths4 cabins13 m2026
from
€5,100
View →
Timeless Planet

Timeless Planet

Bareboat

12 berths4 cabins13 m2022
from
€4,500
View →
Maravigghia

Maravigghia

Bareboat

12 berths4 cabins13 m2025
from
€7,000
View →
Relax Planet

Relax Planet

Bareboat

10 berths4 cabins12 m2019
from
€3,440
View →
Caffè di Sicilia

Caffè di Sicilia

Crewed

13 berths5 cabins19 m2026
from
€14,000
View →
Amia

Amia

Bareboat

13 berths5 cabins14 m2025
from
€7,200
View →
Oasis

Oasis

Crewed

12 berths5 cabins20 m2001
from
€10,000
View →
Hande - Capo Galera

Hande - Capo Galera

Crewed

12 berths6 cabins28 m2003
from
€16,104
View →
Almalu

Almalu

Bareboat

11 berths4 cabins13 m2025
from
€4,470
View →
Sissi

Sissi

Bareboat

12 berths4 cabins13 m2023
from
€4,840
View →
Boreas

Boreas

Bareboat

9 berths4 cabins13 m2018
from
€3,300
View →
Hakuna Matata

Hakuna Matata

Bareboat

11 berths4 cabins14 m2020
from
€4,900
View →
Bambenella

Bambenella

Bareboat

11 berths4 cabins14 m2021
from
€6,100
View →
Oriana

Oriana

Bareboat

12 berths4 cabins14 m2022
from
€6,640
View →
Arianna

Arianna

Bareboat

12 berths4 cabins14 m2022
from
€6,640
View →
Maeva Star

Maeva Star

Crewed

8 berths3 cabins23 m1997
from
€20,000
View →
Maeva Star

Maeva Star

Crewed

8 berths3 cabins23 m1997
from
€2,500
View →
Annemarie

Annemarie

Bareboat

10 berths4 cabins12 m2018
from
€3,800
View →
Bellambriana

Bellambriana

Bareboat

10 berths4 cabins12 m2020
from
€3,800
View →
Orpin

Orpin

Bareboat

10 berths4 cabins13 m2024
from
€5,000
View →
Prince Laurence

Prince Laurence

Bareboat

11 berths4 cabins14 m2019
from
€6,100
View →
Why Not

Why Not

Bareboat

10 berths5 cabins14 m2025
from
€6,700
View →
Pannonica

Pannonica

Bareboat

12 berths5 cabins15 m2022
from
€7,900
View →
New

New

Bareboat

13 berths6 cabins16 m2026
from
€9,600
View →
Giovi II

Giovi II

Crewed

7 berths3 cabins14 m2015
from
€1,300
View →
Amormio

Amormio

Bareboat

12 m2025
from
€2,400
View →
Harmony Planet

Harmony Planet

Bareboat

10 berths4 cabins14 m2021
from
€4,140
View →
Trapani Vela Club

Trapani Vela Club

Bareboat

6 berths3 cabins11 m2023
price on enquiry
View →
Ohana

Ohana

Bareboat

6 berths3 cabins10 m2018
from
€1,850
View →
Albarosa

Albarosa

Bareboat

6 berths2 cabins10 m2017
from
€1,850
View →
Ariele

Ariele

Bareboat

8 berths3 cabins12 m2018
from
€2,000
View →
Rosalba

Rosalba

Bareboat

10 berths4 cabins13 m2023
from
€3,130
View →
Josephine

Josephine

Bareboat

8 berths3 cabins13 m2022
from
€2,200
View →
Theresa

Theresa

Bareboat

8 berths3 cabins12 m2019
from
€2,200
View →
Stella

Stella

Bareboat

8 berths3 cabins12 m2018
from
€2,450
View →
Fantasy Planet

Fantasy Planet

Bareboat

10 berths4 cabins14 m2018
from
€2,130
View →
Arianna

Arianna

Bareboat

12 berths5 cabins15 m2024
from
€3,190
View →
Namaka

Namaka

Bareboat

12 berths5 cabins15 m2021
from
€3,000
View →
Mars Planet

Mars Planet

Bareboat

12 berths5 cabins15 m2015
from
€2,500
View →
Selinde

Selinde

Bareboat

13 berths5 cabins16 m2024
from
€3,630
View →
San Blas

San Blas

Bareboat

12 berths5 cabins16 m2021
from
€3,900
View →
Libery

Libery

Bareboat

12 berths5 cabins16 m2023
from
€4,120
View →
Noe

Noe

Crewed

6 berths3 cabins20 m2004
from
€30,000
View →
Hija del Viento

Hija del Viento

Bareboat

6 berths2 cabins10 m2019
from
€1,470
View →
Pupatella

Pupatella

Bareboat

6 berths2 cabins10 m2019
from
€1,600
View →
Aitna

Aitna

Bareboat

10 berths4 cabins13 m2020
from
€2,600
View →
Nennella

Nennella

Bareboat

10 berths4 cabins13 m2019
from
€2,600
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.