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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,259 Reviews)

    Page 17 of 18 • 418 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine
    Sailing in Fajardo · 6 guests

    Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine

    New
    $200/hour
    Private Sailing Yacht to Coiba National Park – Overnight Option
    Sailing in Panamá · 6 guests

    Private Sailing Yacht to Coiba National Park – Overnight Option

    New
    $120/hour
    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
    Powerboats in Fajardo · 6 guests

    Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

    New
    $650/day
    Captained Charter on 47ft
    Sailing in Coclé Province · 8 guests

    Captained Charter on 47ft

    5.0
    $2,000/day
    Sailing Yacht Charter with amazing crew all inclusive
    Sailing in Panama City · 6 guests

    Sailing Yacht Charter with amazing crew all inclusive

    New
    $865/night
    Your Private Yacht for the Day – Lagoon 46 Full-Day Charter
    Sailing in Fajardo · 6 guests

    Your Private Yacht for the Day – Lagoon 46 Full-Day Charter

    New
    $2,730/day
    2024 Valentine's Week in BVi 🍹🍸👙🤟
    Sailing in Fisher Estate · 8 guests

    2024 Valentine's Week in BVi 🍹🍸👙🤟

    New
    $92,160/day
    Beneteau Oceanis 50’ Luxury Sailing Yacht – Chef on Board - Cartagena
    Sailing in Cartagena · 12 guests

    Beneteau Oceanis 50’ Luxury Sailing Yacht – Chef on Board - Cartagena

    New
    $105/hour
    Beneteau 50 Sailing Yacht Charter in San Blas Islands
    Colón · 10 guests

    Beneteau 50 Sailing Yacht Charter in San Blas Islands

    New
    $1,400/day
    Romantic Sunset Sailing in La Boquilla, Bolívar
    Sailing in La Boquilla · 4 guests

    Romantic Sunset Sailing in La Boquilla, Bolívar

    New
    $260/hour
    53ft Ocean Voyager Catamaran w/Captain, Rendezvous Bay, Anguilla
    Sailing in Anguilla · 28 guests

    53ft Ocean Voyager Catamaran w/Captain, Rendezvous Bay, Anguilla

    New
    $739/hour
    Jamaican Party Boat In Punta Cana Noahs Ark
    Sailing in Bávaro · 50 guests

    Jamaican Party Boat In Punta Cana Noahs Ark

    New
    $265/hour
    Explore the British Virgin Islands on a Boston Whaler
    Powerboats in Wickhams Cay 1 · 10 guests

    Explore the British Virgin Islands on a Boston Whaler

    New
    $2,400/day
    Set Sail Across the East Coast on a 36ft Bavaria Sailing Yacht
    Sailing in Fajardo · 8 guests

    Set Sail Across the East Coast on a 36ft Bavaria Sailing Yacht

    New
    $300+/hour
    Luxury Sailing Experience – The Ultimate Caribbean Adventure
    Sailing in Cruz Bay · 6 guests

    Luxury Sailing Experience – The Ultimate Caribbean Adventure

    New
    $250/hour
    Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda
    Sailing in English Harbour · 6 guests

    Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda

    5.0
    $920/day
    Charter a Cruising Monohull in Foster Hall, Barbados
    Sailing in Less Beholden · 15 guests

    Charter a Cruising Monohull in Foster Hall, Barbados

    New
    $10,667/day
    Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina
    Sailing in Gros Islet · 8 guests

    Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina

    New
    $729/night
    Boston Whaler Center Console Rental in Road Town, Tortola
    Powerboats in Wickhams Cay 1 · 10 guests

    Boston Whaler Center Console Rental in Road Town, Tortola

    New
    $2,400/day
    "Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands
    Sailing in Pointe-a-Pitre · 6 guests

    "Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands

    New
    $9,966/day
    TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter
    Sailing in Wickhams Cay 1 · 20 guests

    TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

    New
    $3,000/day
    51' Neel Cruising Catamaran Rental in Le Marin, Martinique
    Sailing in Rivière-Salée · 9 guests

    51' Neel Cruising Catamaran Rental in Le Marin, Martinique

    New
    $1,545/day
    The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel
    Sailing in El Cortecito · 50 guests

    The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel

    New
    $699/hour
    Beach Monohulls Rental in Saboga, Panama
    Sailing in Contadora · 5 guests

    Beach Monohulls Rental in Saboga, Panama

    New
    $50/hour

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    Sailing Reviews in Caribbean

    1. FO

      Fernando

      Captained Charter on 47ft

      Was the best trip ever! Really recommend this trip and hope soon have a weekend trip in this catamaran

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