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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.7
    (2,366 Reviews)

    Page 10 of 18 • 432 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch
    Powerboats in Sosúa · 70 guests

    Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

    New
    $242/hour
    Instant Book
    Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)
    Events in Bávaro · 100 guests

    Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

    5.0
    $240/hour
    Maxicat 65ft Private Party Catamaran in Cartagena
    Sailing in Cartagena · 80 guests

    Maxicat 65ft Private Party Catamaran in Cartagena

    New
    Superowner
    $838/hour
    Cruising Catamaran Rental in Puerto Plata, Puerto Plata
    Sailing in Barrio Las Yaguitas · 80 guests

    Cruising Catamaran Rental in Puerto Plata, Puerto Plata

    1.0
    Superowner
    Best of 2026
    $183/hour
    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena
    Sailing in Cartagena · 23 guests

    An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

    New
    Superowner
    $231/hour
    Punta Cana - FAMILY BOAT
    Sailing in Bávaro · 200 guests

    Punta Cana - FAMILY BOAT

    New
    $160/hour
    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios
    Powerboats in Ocho Rios · 100 guests

    Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

    New
    $654/hour
    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience
    Events in Sosúa · 25 guests

    Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

    New
    $135/hour
    39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia
    Events in Bávaro · 12 guests

    39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

    New
    $1,910/day
    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling
    Sailing in Montego Bay · 60 guests

    Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

    New
    $1,176/hour
    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia
    Sailing in Cartagena · 80 guests

    Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

    New
    Superowner
    $5,000/day
    Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)
    Sailing in El Cortecito · 70 guests

    Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)

    New
    $644/hour
    Instant Book
    Bahia de las Aguilas- Private Catamaran Cruise
    Events in Dominican Republic · 70 guests

    Bahia de las Aguilas- Private Catamaran Cruise

    New
    $500/hour
    Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music
    Sailing in Bávaro · 70 guests

    Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

    New
    $500/hour
    Instant Book
    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
    Sailing in Fort Lauderdale · 12 guests

    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

    5.0
    $450/hour
    Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena
    Sailing in Cartagena · 14 guests

    Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena

    New
    Superowner
    $200/hour
    Ocho Rios Private Sunset Catamaran with Dinner & Open Bar
    Powerboats in Ocho Rios · 100 guests

    Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

    New
    $817/hour
    Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne
    Tours in Miami Beach · 10 guests

    Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne

    New
    Superowner
    $159+/hour
    Sail from Boynton Beach to Lake Boca
    Sailing in Boynton Beach · 12 guests

    Sail from Boynton Beach to Lake Boca

    New
    Superowner
    $126+/hour
    47ft Private Custom Catamaran Charter in Fajardo, Puerto Rico
    Sailing in Fajardo · 44 guests

    47ft Private Custom Catamaran Charter in Fajardo, Puerto Rico

    New
    $800/hour
    Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia
    Sailing in Cartagena · 12 guests

    Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

    New
    Superowner
    $150/hour
    Sailing catamaran in USVI
    Sailing in Charlotte Amalie · 6 guests

    Sailing catamaran in USVI

    5.0
    $1,300/day
    Twin Island Paradise Snorkel Tour
    Tours in Basseterre · 45 guests

    Twin Island Paradise Snorkel Tour

    New
    $29/hour
    Limited Availability
    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull
    Sailing in Cartagena · 10 guests

    Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull

    New
    Superowner
    $163/hour

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. Evan

      Evan

      Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

      Amazing people to deal with ! Highly recommend

    2. erkan

      erkan

      57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

      Crew , boat , owner … they were the best !

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