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Sailboat Charter Caribbean

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2000 2027
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100% Online Booking & Secure Payments 100% Online Booking & Secure Payments
  1. -5%
    Windward Spirit
    Jeanneau Sun Odyssey 54 DS | Windward Spirit — crewed sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2003 built
    Cabins
    4 cabins
    Berths
    8 berths
    Toilets
    4 toilets
    Sail Type
    full batten
    Bow Thruster
    bowthruster
    Length 16.8 m
    Air Condition
    Air Condition
    Generator
    Generator
    Solar Panels
    Solar Panels
    CREWED
    from
    6,658 $ / week (15–22 May 2027)
    View Details
  2. -10%
    LUNA ROSSA
    Dufour 430 GL | LUNA ROSSA — bareboat or skippered sailboat La Marina Bas du Fort, Guadeloupe, Caribbean
    Build Year
    2023 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    2 toilets
    Sail Type
    full batten
    Length 13.2 m
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    2,103 $ / week (14–21 Aug 2027)
    View Details
  3. Early Bird Discounts up to 40%
    Early Bird Discounts up to 40%
  4. -5%
    Phat Dolphin
    Jeanneau Sun Odyssey 479 | Phat Dolphin — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2019 built
    Cabins
    3 cabins
    Berths
    6 berths
    Toilets
    3 toilets
    Bow Thruster
    bowthruster
    Length 14.4 m
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    4,705 $ / week (10–17 Jul 2027)
    View Details
  5. -5%
    Sea Wolf
    Jeanneau Sun Odyssey 44 DS | Sea Wolf — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2016 built
    Cabins
    3 cabins
    Berths
    6 berths
    Toilets
    2 toilets
    Length 13.3 m
    Air Condition
    Air Condition
    Generator
    Generator
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,962 $ / week (10–17 Jul 2027)
    View Details
  6. -5%
    Patches
    Bavaria Cruiser 41 | Patches — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2018 built
    Cabins
    2 cabins
    Berths
    4 berths
    Toilets
    2 toilets
    Length 12.4 m
    Air Condition
    Air Condition
    Generator
    Generator
    BAREBOAT SKIPPERED
    from
    3,625 $ / week (10–17 Jul 2027)
    View Details
  7. -5%
    Calia
    Jeanneau Sun Odyssey 449 | Calia — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2016 built
    Cabins
    4 cabins
    Berths
    7 berths
    Toilets
    2 toilets
    Bow Thruster
    bowthruster
    Length 13.3 m
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    4,160 $ / week (10–17 Jul 2027)
    View Details
  8. -10%
    Spicy Rum
    Dufour 37 | Spicy Rum — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2024 built
    Cabins
    3 cabins
    Berths
    6 berths
    Toilets
    1 toilets
    Sail Type
    full batten
    Length 10.8 m
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    2,742 $ / week (4–11 Sep 2027)
    View Details
  9. -5%
    Makin Memories
    Jeanneau Sun Odyssey 419 | Makin Memories — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2018 built
    Cabins
    3 cabins
    Berths
    6 berths
    Toilets
    2 toilets
    Length 12.8 m
    Solar Panels
    Solar Panels
    BAREBOAT SKIPPERED
    from
    3,733 $ / week (10–17 Jul 2027)
    View Details
  10. -10%
    HOPPER
    Dufour 520 GL | HOPPER — bareboat or skippered sailboat La Marina Bas du Fort, Guadeloupe, Caribbean
    Build Year
    2019 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 15.2 m
    Air Condition
    Air Condition
    Generator
    Generator
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    2,418 $ / week (14–21 Aug 2027)
    View Details
  11. -10%
    BRAQUE
    Dufour 520 GL | BRAQUE — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2019 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 15.2 m
    Air Condition
    Air Condition
    Generator
    Generator
    BAREBOAT SKIPPERED
    from
    2,865 $ / week (5–12 Jun 2027)
    View Details
  12. -10%
    NOSY BE_DB
    Jeanneau Sun Odyssey 519 | NOSY BE_DB — bareboat or skippered sailboat St. Martin, St. Martin, Caribbean
    Build Year
    2018 built
    Cabins
    5 cabins
    Berths
    13 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 15.8 m
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    3,196 $ / week (29 May – 5 Jun 2027)
    View Details
  13. -5%
    Paradise Found
    Jeanneau Jeanneau 54 | Paradise Found — bareboat or skippered sailboat Blue Lagoon Marina, St. Vincent, Caribbean
    Build Year
    2017 built
    Cabins
    3 cabins
    Berths
    6 berths
    Toilets
    3 toilets
    Sail Type
    furling/roll
    Length 16.2 m
    Air Condition
    Air Condition
    Generator
    Generator
    BAREBOAT SKIPPERED
    from
    5,151 $ / week (10–17 Jul 2027)
    View Details
  14. -10%
    GILMITH
    Jeanneau Sun Loft 47 | GILMITH — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2020 built
    Cabins
    6 cabins
    Berths
    13 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Length 14.4 m
    BAREBOAT SKIPPERED
    from
    2,355 $ / week (5–12 Jun 2027)
    View Details
  15. -10%
    GELMIR
    Jeanneau Sun Loft 47 | GELMIR — bareboat or skippered sailboat La Marina Bas du Fort, Guadeloupe, Caribbean
    Build Year
    2020 built
    Cabins
    6 cabins
    Berths
    13 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Length 14.4 m
    BAREBOAT SKIPPERED
    from
    1,682 $ / week (14–21 Aug 2027)
    View Details
  16. -10%
    KLIMT
    Beneteau Oceanis 51.1 | KLIMT — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2019 built
    Cabins
    5 cabins
    Berths
    13 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 15.9 m
    Air Condition
    Air Condition
    Generator
    Generator
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    2,865 $ / week (5–12 Jun 2027)
    View Details
  17. -10%
    KLEE
    Beneteau Oceanis 51.1 | KLEE — bareboat or skippered sailboat St. Martin, St. Martin, Caribbean
    Build Year
    2019 built
    Cabins
    5 cabins
    Berths
    13 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 15.9 m
    Air Condition
    Air Condition
    Generator
    Generator
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    3,811 $ / week (29 May – 5 Jun 2027)
    View Details
  18. -10%
    IBIS
    Dufour 460 GL | IBIS — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2020 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 14.2 m
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    2,618 $ / week (5–12 Jun 2027)
    View Details
  19. -10%
    ALBATROSS
    Dufour 460 GL | ALBATROSS — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2020 built
    Cabins
    5 cabins
    Berths
    12 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 14.2 m
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    2,618 $ / week (5–12 Jun 2027)
    View Details
  20. STRAUSS
    Beneteau Oceanis 45 | STRAUSS — bareboat or skippered sailboat La Marina Bas du Fort, Guadeloupe, Caribbean
    Build Year
    2017 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    2 toilets
    Length 13.9 m
    BAREBOAT SKIPPERED
    from
    3,767 $ / week (10–17 Apr 2027)
    View Details
  21. -10%
    GALDOR
    Jeanneau Sun Loft 47 | GALDOR — bareboat or skippered sailboat La Marina Bas du Fort, Guadeloupe, Caribbean
    Build Year
    2019 built
    Cabins
    6 cabins
    Berths
    13 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Length 14.4 m
    BAREBOAT SKIPPERED
    from
    1,682 $ / week (14–21 Aug 2027)
    View Details
  22. -10%
    GLOXINIA
    Dufour 470 | GLOXINIA — bareboat or skippered sailboat La Marina Bas du Fort, Guadeloupe, Caribbean
    Build Year
    2023 built
    Cabins
    5 cabins
    Berths
    11 berths
    Toilets
    3 toilets
    Sail Type
    full batten
    Length 14.9 m
    Watermaker
    Watermaker
    BAREBOAT SKIPPERED
    from
    2,176 $ / week (14–21 Aug 2027)
    View Details
  23. -20%
    BESRA
    Dufour 430 GL | BESRA — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2020 built
    Cabins
    4 cabins
    Berths
    10 berths
    Toilets
    2 toilets
    Sail Type
    full batten
    Length 13.2 m
    BAREBOAT SKIPPERED
    from
    2,925 $ / week (5–12 Dec 2026)
    View Details
  24. -10%
    GERETH
    Jeanneau Sun Loft 47 | GERETH — bareboat or skippered sailboat Le Marin, Martinique, Caribbean
    Build Year
    2020 built
    Cabins
    6 cabins
    Berths
    13 berths
    Toilets
    4 toilets
    Sail Type
    furling/roll
    Length 14.4 m
    BAREBOAT SKIPPERED
    from
    2,355 $ / week (5–12 Jun 2027)
    View Details
  25. -10%
    ALHUCHAR 5
    Beneteau Oceanis 40.1 | ALHUCHAR 5 — bareboat or skippered sailboat St. Martin, St. Martin, Caribbean
    Build Year
    2023 built
    Cabins
    3 cabins
    Berths
    8 berths
    Toilets
    2 toilets
    Sail Type
    full batten
    Length 12.9 m
    Air Condition
    Air Condition
    BAREBOAT SKIPPERED
    from
    2,492 $ / week (27 May – 3 Jun 2028)
    View Details
  26. -10%
    CONTIGO
    Dufour 412 GL | CONTIGO — bareboat or skippered sailboat St. Martin, St. Martin, Caribbean
    Build Year
    2022 built
    Cabins
    3 cabins
    Berths
    8 berths
    Toilets
    2 toilets
    Sail Type
    full batten
    Length 12.7 m
    BAREBOAT SKIPPERED
    from
    2,439 $ / week (29 May – 5 Jun 2027)
    View Details

Sailboat Rental in Caribbean

Chartering a Sailboat in Caribbean is a simple way to explore the coastline and surrounding waters. With 29 Sailboat available in Caribbean 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 Caribbean 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 301 $ 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

Book with Trusted Partners at the highest standards.
24/7 Concierge Service & Unbiased Advice

24/7 Concierge Service & Unbiased Advice

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.
Client Loyalty Reward Scheme

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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