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Sailboat Charter Sicily

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  1. -12%
    Arianna
    Beneteau Oceanis 46.1 | Arianna — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2024 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 14.6 m
    Watermaker
    Watermaker
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,298 $ / week (3–10 Apr 2027)
    View Details
  2. -12%
    Clelia
    Dufour 470 | Clelia — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2024 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 14.9 m
    Watermaker
    Watermaker
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,400 $ / week (3–10 Apr 2027)
    View Details
  3. Early Bird Discounts up to 40%
    Early Bird Discounts up to 40%
  4. -12%
    Perla
    Dufour 470 | Perla — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2024 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 14.9 m
    Watermaker
    Watermaker
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,400 $ / week (3–10 Apr 2027)
    View Details
  5. -12%
    Selinde
    Beneteau Oceanis 51.1 | Selinde — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2024 built
    Cabins
    5 cabins
    Berths
    13 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 15.9 m
    Watermaker
    Watermaker
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,864 $ / week (3–10 Apr 2027)
    View Details
  6. -20%
    Euphoria Planet
    Dufour 56 Exclusive | Euphoria Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2022 built
    Cabins
    4 cabins
    Berths
    11 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 17.2 m
    Air Condition
    Air Condition
    Generator
    Generator
    BAREBOAT SKIPPERED
    from
    4,066 $ / week (3–10 Apr 2027)
    View Details
  7. -20%
    Wish Planet
    Dufour 530 | Wish Planet — bareboat or skippered sailboat Marina Si.ti.mar, Sicily, Italy
    Build Year
    2022 built
    Cabins
    5 cabins
    Berths
    13 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 16.4 m
    Air Condition
    Air Condition
    Generator
    Generator
    BAREBOAT SKIPPERED
    from
    3,717 $ / week (3–10 Apr 2027)
    View Details
  8. -20%
    Si Puo Fare
    Dufour 430 | Si Puo Fare — bareboat or skippered sailboat Marina Si.ti.mar, Sicily, Italy
    Build Year
    2023 built
    Cabins
    3 cabins
    Berths
    8 berths
    Toilets
    2 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 13.2 m
    Air Condition
    Air Condition
    BAREBOAT SKIPPERED
    from
    2,416 $ / week (3–10 Apr 2027)
    View Details
  9. -20%
    Discovery Planet
    Dufour 460 GL | Discovery Planet — bareboat or skippered sailboat Marina Si.ti.mar, Sicily, Italy
    Build Year
    2021 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,641 $ / week (3–10 Apr 2027)
    View Details
  10. -20%
    Mania Planet
    Dufour 460 GL | Mania Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2021 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,641 $ / week (3–10 Apr 2027)
    View Details
  11. -33%
    Taddarita
    Dufour 530 | Taddarita — bareboat or skippered sailboat Palermo, Marina di La Cala, Sicily, Italy
    Build Year
    2025 built
    Cabins
    5 cabins
    Berths
    13 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 16.4 m
    Air Condition
    Air Condition
    Generator
    Generator
    Watermaker
    Watermaker
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    4,177 $ / week (3–10 Apr 2027)
    View Details
  12. -33%
    Bedda Matri
    Dufour 470 | Bedda Matri — bareboat or skippered sailboat Palermo, Marina di La Cala, Sicily, Italy
    Build Year
    2025 built
    Cabins
    4 cabins
    Berths
    11 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 14.9 m
    Air Condition
    Air Condition
    Generator
    Generator
    Watermaker
    Watermaker
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,399 $ / week (3–10 Apr 2027)
    View Details
  13. -20%
    Smile Planet
    Dufour 360 GL | Smile Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2022 built
    Cabins
    2 cabins
    Berths
    6 berths
    Toilets
    1 toilets
    Sail Type
    classic/standard
    Length 10.7 m
    BAREBOAT SKIPPERED
    from
    1,615 $ / week (3–10 Apr 2027)
    View Details
  14. -20%
    Sympathy Planet
    Dufour 390 GL | Sympathy Planet — bareboat or skippered sailboat Marina Si.ti.mar, Sicily, Italy
    Build Year
    2021 built
    Cabins
    3 cabins
    Berths
    7 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 11.9 m
    BAREBOAT SKIPPERED
    from
    1,887 $ / week (3–10 Apr 2027)
    View Details
  15. -20%
    Dream Planet
    Dufour 520 GL | Dream Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2020 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 15.2 m
    BAREBOAT SKIPPERED
    from
    2,868 $ / week (3–10 Apr 2027)
    View Details
  16. -20%
    Adventure Planet
    Dufour 460 GL | Adventure Planet — bareboat or skippered sailboat Marsala, Sicily, Italy
    Build Year
    2020 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,548 $ / week (3–10 Apr 2027)
    View Details
  17. -20%
    Wonder Planet
    Dufour 460 GL | Wonder Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2020 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,548 $ / week (3–10 Apr 2027)
    View Details
  18. -20%
    Summer Planet
    Dufour 460 GL | Summer Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2019 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,453 $ / week (3–10 Apr 2027)
    View Details
  19. -20%
    Holiday Planet
    Dufour 520 GL | Holiday Planet — bareboat or skippered sailboat Marina Si.ti.mar, Sicily, Italy
    Build Year
    2019 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 15.2 m
    BAREBOAT SKIPPERED
    from
    2,765 $ / week (3–10 Apr 2027)
    View Details
  20. -20%
    Fun Planet
    Dufour 460 GL | Fun Planet — bareboat or skippered sailboat Marsala, Sicily, Italy
    Build Year
    2017 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,359 $ / week (3–10 Apr 2027)
    View Details
  21. -20%
    Neptune Planet
    Dufour 460 GL | Neptune Planet — bareboat or skippered sailboat Marsala, Sicily, Italy
    Build Year
    2016 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 14.2 m
    BAREBOAT SKIPPERED
    from
    2,264 $ / week (3–10 Apr 2027)
    View Details
  22. -33%
    Granfio
    Dufour 54 | Granfio — bareboat or skippered sailboat Capo D'orlando Marina, Sicily, Italy
    Build Year
    2026 built
    Cabins
    4 cabins
    Berths
    11 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 16.8 m
    Air Condition
    Air Condition
    Generator
    Generator
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    4,383 $ / week (3–10 Apr 2027)
    View Details
  23. -20%
    Hija del Viento
    Jeanneau Sun Odyssey 319 | Hija del Viento — bareboat or skippered sailboat Marina Si.ti.mar, Sicily, Italy
    Build Year
    2019 built
    Cabins
    2 cabins
    Berths
    6 berths
    Toilets
    1 toilets
    Sail Type
    classic/standard
    Length 9.8 m
    BAREBOAT SKIPPERED
    from
    1,416 $ / week (3–10 Apr 2027)
    View Details
  24. -20%
    Friend Planet
    Dufour 390 GL | Friend Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2019 built
    Cabins
    3 cabins
    Berths
    8 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 11.9 m
    BAREBOAT SKIPPERED
    from
    1,887 $ / week (3–10 Apr 2027)
    View Details
  25. -20%
    Happy Planet
    Dufour 360 GL | Happy Planet — bareboat or skippered sailboat Portorosa, Sicily, Italy
    Build Year
    2018 built
    Cabins
    2 cabins
    Berths
    6 berths
    Toilets
    1 toilets
    Sail Type
    full batten
    Length 10.7 m
    BAREBOAT SKIPPERED
    from
    1,332 $ / week (3–10 Apr 2027)
    View Details
  26. -20%
    Mars Planet
    Beneteau Oceanis 48 | Mars Planet — bareboat or skippered sailboat Marsala, Sicily, Italy
    Build Year
    2015 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    furling/roll
    Bow Thruster
    bowthruster
    Length 14.6 m
    BAREBOAT SKIPPERED
    from
    2,755 $ / week (3–10 Apr 2027)
    View Details

Sailboat Rental in Sicily

Chartering a Sailboat in Sicily is a simple way to explore the coastline and surrounding waters. With 88 Sailboat available in Sicily and more nearby, there's a wide range of options for different group sizes and preferences.

Sailboats give you a traditional wind-powered experience, ideal for those who enjoy hands-on sailing.

You can rent a Sailboat in Sicily for a short cruise or a longer holiday, with the choice of bareboat or skippered options depending on your experience. All boats are regularly maintained for safety and comfort. Prices begin at 220 $ per day, with transparent costs and no hidden fees.

Browse available yachts, compare features, and book your Sailboat easily with real-time availability and secure payment. Yacht4Less connects you with trusted rentals worldwide, making it straightforward to plan your trip with confidence.



Why book with Yacht4Less?

15,000+ Verified Boats & Top Charter Companies

15,000+ Verified Boats & Top Charter Companies

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24/7 Concierge Service & Unbiased Advice

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Support before, during & after your yacht booking.
50+ Global Sailing Destinations

50+ Global Sailing Destinations

Cruise the Mediterranean, Caribbean & Exotics.
Expert Broker Advisory & Tailor-made Trips

Expert Broker Advisory & Tailor-made Trips

Custom tips for families, couples & groups.
Best Yacht Charter Price Guarantee

Best Yacht Charter Price Guarantee

Early Bird & Last Minute yacht & catamaran charters.
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Client Loyalty Reward Scheme

Repeaters get benefits on every Yacht4less booking.
Transparent Pricing & No Booking Fees

Transparent Pricing & No Booking Fees

Clear quotes, real-time availability, no hidden costs.
100% Online Booking & Secure Payments

100% Online Booking & Secure Payments

Search, book & pay online with confidence.
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