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  1. Dufour 460 GL

    Dufour 460 GL

    Portorosa

    8,6

    2018 14.15 meters

    4 Cabins 10 Berths

    Barbecue, Outdoor speakers, Bimini

    from $3,278

    See the boat
  2. Dufour 382 GL

    Dufour 382 GL

    Portorosa

    8,1

    2017 11.23 meters

    3 Cabins 6 Berths

    Deck shower, Cockpit cushions, Electric windlass

    from $1,346

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  3. Dufour 520 GL

    Dufour 520 GL

    Portorosa

    8,3

    2019 15.2 meters

    5 Cabins 12 Berths

    Barbecue, Outdoor speakers, Bimini

    from $3,980

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  4. Oceanis 46.1

    8,6

    2019 14.6 meters

    4 Cabins 10 Berths

    Bimini, Electric converter, Electric winch

    from $3,617

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  5. Need some advice?
    Pierre
    Pierre your cruise expert
    Pierre is a French-American sailing expert living between San Francisco and Barcelona, he regularly meets with our European partners to guarantee you the best service and the most reliable boats.
    • Let's find the best cruise together thanks to our 30 years of experience
    • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.
  6. Sun Odyssey 490

    Sun Odyssey 490

    Capo d'Orlando

    7,9

    2019 14.45 meters

    6 Cabins 12 Berths

    Bimini, Electric winch, Bow thruster

    from $4,202

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  7. Sun Odyssey 490

    Sun Odyssey 490

    Capo d'Orlando

    2019 14.45 meters

    6 Cabins 12 Berths

    Electric windlass, Freezer, Bow thruster

    from $3,992

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  8. Dufour 512 GL

    Dufour 512 GL

    Portorosa

    8,2

    2017 15.5 meters

    4 Cabins 10 Berths

    Desalination system, Fully battened mainsail, Electric windlass

    from $1,773

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  9. Oceanis 46.1

    Oceanis 46.1

    Capo d'Orlando

    9,2

    2020 14.6 meters

    5 Cabins 10 Berths

    Bimini, Electric converter, Electric winch

    from $3,851

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  10. Oceanis 45

    Oceanis 45

    Portorosa

    7,7

    2019 13.85 meters

    4 Cabins 10 Berths

    Bimini, Electric windlass, Electric winch

    from $3,453

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  11. Dufour 460 GL

    Dufour 460 GL

    Portorosa

    8,1

    2019 14.15 meters

    4 Cabins 10 Berths

    Barbecue, Bimini, Fully battened mainsail

    from $2,692

    See the boat
  12. Need some advice?
    Pierre
    Pierre your cruise expert
    Pierre is a French-American sailing expert living between San Francisco and Barcelona, he regularly meets with our European partners to guarantee you the best service and the most reliable boats.
    • Let's find the best cruise together thanks to our 30 years of experience
    • Best price guaranteed: If you find a lower price somewhere else, we commit to matching it.
  13. Sun Odyssey 410

    9,5

    2022 12.35 meters

    3 Cabins 8 Berths

    Bimini, Fully battened mainsail, Spacious deck

    from $2,868

    See the boat
  14. Dufour 470 GL

    Dufour 470 GL

    Portorosa

    8,3

    2024 14.85 meters

    5 Cabins 11 Berths

    Desalination system, Electric windlass, GPS cockpit plotter

    from $2,090

    See the boat
  15. Dufour 430 GL

    Dufour 430 GL

    Portorosa

    7,9

    2024 13.24 meters

    4 Cabins 10 Berths

    Barbecue, Outdoor speakers, Bimini

    from $3,629

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  16. Oceanis 46.1

    Oceanis 46.1

    Portorosa

    7,4

    2023 14.6 meters

    4 Cabins 10 Berths

    Bimini, Electric converter, Electric winch

    from $4,039

    See the boat
  17. Dufour 520 GL

    7,6

    2019 15.2 meters

    5 Cabins 12 Berths

    Barbecue, Bimini, Fully battened mainsail

    from $3,044

    See the boat
  18. Dufour 470 GL

    Dufour 470 GL

    Portorosa

    8,5

    2023 14.85 meters

    5 Cabins 9 Berths

    Desalination system, Hi-Fi system, Fully battened mainsail

    from $2,090

    See the boat
  19. Dufour 360 GL

    Dufour 360 GL

    Portorosa

    7,7

    2022 10.3 meters

    2 Cabins 6 Berths

    Bimini, Electric converter, Fully battened mainsail

    from $1,756

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  20. Dufour 56 Exclusive

    7,7

    2022 16.3 meters

    5 Cabins 11 Berths

    Heating, Barbecue, Bimini

    from $4,027

    See the boat
  21. Bavaria Cruiser 46 Style

    Bavaria Cruiser 46 Style

    Palermo - Puntone - Marina di Scarlino

    6,6

    2017 14.27 meters

    4 Cabins 10 Berths

    Electric windlass, Bow thruster, Mainsail on furler

    from $2,927

    See the boat
  22. Oceanis 41.1

    Oceanis 41.1

    Portorosa

    9,1

    2017 12.43 meters

    3 Cabins 8 Berths

    Bimini, Electric windlass, GPS cockpit plotter

    from $1,908

    See the boat
Sailboat : 211 boats found

Sicily sailboat charter with or without skipper

Last updated on 3 February 2026

Why charter a sailboat in Sicily?

Bathed by the crystal-clear waters of the Mediterranean Sea, Sicily is a land rich in history with one of the most varied artistic and cultural heritages, thanks to the influences of the different peoples who have inhabited the island over the centuries. With a sailboat charter in Sicily, you can discover some of the most unique landscapes: from volcanic territories to Greek ruins surrounded by Mediterranean scrubland. Thanks to its shallow draft, it slips into secluded coves and confidential anchorages, away from the most frequented stops. Sicily is a land of sailors, which is why there are numerous nautical bases for sailing to the various archipelagos, including the Aeolian Islands and the Egadi Islands. Wherever you decide to sail in Sicily, you can try its rich gastronomy and discover dream beaches and hidden bays to explore with a sailboat charter.

Cruising around Sicily and the Aeolian Islands by sailboat means opting for authentic sailing, at the rhythm of the wind and the elements. 

Services offered for your sailboat charter in Sicily

  • Opting for a sailboat charter without a skipper is ideal if one of your crew members has sailing experience. You will enjoy complete freedom to build your itinerary in Sicily and the Aeolian Islands, choose your anchorages, and experience a cruise in total privacy.
  • Opting for a sailboat charter with a skipper is the perfect alternative if no one in your group knows how to sail or if you want a hassle-free vacation. The skipper takes care of the navigation and, thanks to their knowledge of local conditions, will guide you to the best shelters, anchorages, and stops around the Aeolian Islands.
  • Opting for a sailboat charter with a professional crew is recommended if you are looking for a higher level of comfort. Depending on the boat, the crew may include a captain and onboard staff (hostess, cook…) who will dedicate themselves to your well-being to offer you a premium cruise in Sicily, without worrying about the organization on board.

What is the price for a sailboat charter in Sicily?

The following table presents an estimate of average prices for a sailboat charter in Sicily for 1 week. Note that these rates may vary depending on the season, availability, model type, age of the boat, and other factors.

 

High season 

July - August

Mid season

May - June and September - October

Low season 

November to March

Monohull 2 cabins

€2,300

€1,400

€1,300

Monohull 3 cabins

€3,000

€1,700

€1,900

Monohull 4 cabins

€3,900

€2,300

€2,600

Monohull 5 cabins

€5,300

€3,000

€3,200

Monohull 6+ cabins

€5,900

€3,500

€3,800

 

The price includes: the boat charter and the main equipment on board (sails, tableware, wifi, dinghy, bedding, and outboard motor).

The price does not include: insurance, port and mooring fees, skipper, hostess, cleaning which is often included in a mandatory pack, extras (kayak, stand-up paddleboard…), and provisioning.

If chartering a sailboat in Sicily and the Aeolian Islands appeals to you, please do not hesitate to contact us directly to consult our rates. Costs can fluctuate considerably depending on the type of sailboat. Lina, our specialist in crews and premium boats, will be delighted to present our best offers to you.

We suggest you choose our cancellation insurance when chartering a boat in the Caribbean. It offers protection for the entire crew, unlike personal cancellation insurance or that offered by your credit card, which generally only protects the cardholder.

We also recommend that our clients take out security deposit waiver insurance (mandatory if you hire a professional skipper). Even the most seasoned sailors are not immune to incidents at sea. With this insurance, you will have the possibility of recovering a large part of your deposit in case of damage during navigation.

Where to sail in Sicily?

  • The Aeolian Islands form the emblematic volcanic archipelago of the region: Lipari, Vulcano, Stromboli, Salina… Here, the landscapes oscillate between smoking craters, black cliffs, and coves with crystal-clear waters. The distances between the islands remain reasonable, which allows you to easily alternate between wild anchorages during the day and lively evenings in the small ports. For an Aeolian Islands yacht charter, we recommend a one-week cruise, but if you have fewer days, you cannot miss Stromboli with its volcanic atmosphere and Panarea. To the north, Capo d'Orlando, Portorosa, and Milazzo are the best bases for a vacation on these islands. 
  • The Egadi Islands (Favignana, Levanzo, Marettimo) offer a completely different face: waters of exceptional clarity, well-sheltered bays, and a more preserved atmosphere. It is the ideal playground for a cruise focused on swimming and snorkeling, far from the summer bustle of the Aeolian Islands. Trapani and Marsala are two ideal bases for discovering the magnificent beaches of the islands of Favignana, Levanzo, and Marettimo.
  • The Sicilian coast, finally, allows you to combine sailing and shore stops to discover the cultural and gastronomic riches of the island. A particularly suitable option if you wish to limit long crossings and keep fallback solutions (ports, marinas) in case of unpredictable weather. Sicily stands out above all for its diversity, which is reflected in the unique character of each coastal town. A sailing cruise in Sicily departing from Palermo, the capital, is an ideal base for your trip: you will be seduced by its mix of artistic styles and its Arab-Norman architecture. Along the northwest coast, do not miss San Vito Lo Capo, one of the most renowned seaside resorts in the region. On the opposite side, to the east, the province of Syracuse will seduce you with its history-laden villages and its preserved beaches bordered by untouched nature. From Syracuse, you can even consider a crossing to Malta. Going up the south coast, a stop at Agrigento will open the doors to the famous Valley of the Temples.

When to sail in Sicily?

The climate in Sicily is pleasant for most of the year, with temperatures generally varying between 57°F and 86°F depending on the season. It is therefore possible to go on a cruise over a long period, particularly from spring to fall to discover the most beautiful beaches in Sicily. However, it should be noted that July and August are the hottest and busiest months, sometimes with wind and rougher seas depending on the areas. Sicily is therefore an ideal destination for those looking for a Mediterranean cruise, between authentic villages, clear waters, and beautiful sailing, while enjoying a mild climate from spring until late season.

Here is an average of the temperatures recorded in recent years in Sicily:

 JanFebMarAprMayJunJulAugSepOctNovDec
Air min (°F)45°45°46°50°55°63°68°68°64°59°54°46°
Air max (°F)57°57°61°66°72°79°86°86°82°73°66°61°
Sea water (°F)59°57°57°59°64°72°79°79°77°72°68°63°

 

Sailing conditions in Sicily and the Aeolian Islands depend greatly on your sailing area and your exposure to the winds. The prevailing winds are the Mistral and the Tramontana (coming from the northwest) as well as the Sirocco (coming from the southeast), which is warmer and sometimes laden with sand. In summer, thermal breezes often develop in the afternoon and can strengthen the wind, particularly in the passages between the islands. In more open areas, the wind can easily reach force 4 to 6 (approximately 15 to 25 knots, or 17 to 29 mph), while some bays and leeward coasts remain more sheltered and comfortable for anchoring.

Documents required for sailing without a skipper in Sicily

In Sicily, you will need a boat license to skipper a monohull sailboat. You will also need to present a sailing CV detailing your main sailing experiences, ideally on boats similar in size and program (coastal navigation, maneuvers, anchorages).

How do I finalize my sailboat booking in Sicily?

As soon as we receive your charter request, an advisor will contact you to discuss your cruise project. They will then send you boat proposals suited to your needs by email. After selecting the boat of your choice, you can pay a deposit from your client area to validate the charter and reserve the boat.

 

Good to know

Number of boats available 1 375
Types of service Skipper, Hostess, Sailor, Chef (meals not included), Engineer
Average price per week $8,388
Minimum weekly price $773
Maximum price per week $128,766

Need some advice?
Pierre
Pierre your cruise expert
Contact our advisors to find your future cruise
  • Let's find the best cruise together thanks to our 30 years of experience
  • Access our catalog of boats rated by our customers and certified yacht charter companies

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