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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,354 Reviews)

    Page 9 of 19 • 440 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Bahia de las Aguilas- Private Catamaran Cruise
    Events in Dominican Republic · 70 guests

    Bahia de las Aguilas- Private Catamaran Cruise

    New
    $500/hour
    Private Charters In Simpson Bay or Philipsburg
    Caribbean · 30 guests

    Private Charters In Simpson Bay or Philipsburg

    5.0
    $3,300/day
    3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
    Powerboats in Sosúa · 15 guests

    3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

    New
    $332/hour
    42' Luxury Catamaran Sailboat
    Sailing in Miami · 6 guests

    42' Luxury Catamaran Sailboat

    New
    $285/hour
    Sail from Delray Beach to Lake Boca
    Sailing in Delray Beach · 12 guests

    Sail from Delray Beach to Lake Boca

    1.0
    Superowner
    $125+/hour
    Luxury Lagoon 50' Catamaran Charter In Grenada and The Grenadines
    Sailing in Saint George's · 10 guests

    Luxury Lagoon 50' Catamaran Charter In Grenada and The Grenadines

    5.0
    $200/hour
    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
    Caribbean · 10 guests

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    5.0
    $1,200/day
    Punta Cana - PRIVATE BOAT MAX BBQ
    Sailing in Bávaro · 40 guests

    Punta Cana - PRIVATE BOAT MAX BBQ

    New
    $575/hour
    Saona Island 50' Private Sailing Yacht tour
    Sailing in Bávaro · 10 guests

    Saona Island 50' Private Sailing Yacht tour

    New
    Superowner
    Best of 2026
    $100/hour
    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
    Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia
    Events in Bávaro · 200 guests

    Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia

    New
    Superowner
    Best of 2026
    $17/hour
    Luxury 52 Catamaran With AC - Price include 2 People
    Sailing in Guna Yala Comarca · 8 guests

    Luxury 52 Catamaran With AC - Price include 2 People

    5.0
    $3,000/day
    Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music
    Sailing in Bávaro · 70 guests

    Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

    New
    $255/hour
    Sailing live aboard Charter in Montego Bay, Jamaica
    Sailing in Montego Bay · 15 guests

    Sailing live aboard Charter in Montego Bay, Jamaica

    5.0
    $950/day
    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ
    Sailing in Punta Cana · 70 guests

    Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ

    New
    $125+/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
    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
    Sailing Adventure on Bay in Miami on Tartan Sailboat!
    Sailing in Key Biscayne · 6 guests

    Sailing Adventure on Bay in Miami on Tartan Sailboat!

    5.0
    $100/hour
    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included
    Powerboats in Nassau · 15 guests

    55' Nisi Catamaran – Private Bahamas Day Charter- Gratuity and Tax included

    New
    $1,385+/hour
    Sailing catamaran in USVI
    Sailing in Charlotte Amalie · 6 guests

    Sailing catamaran in USVI

    5.0
    $1,300/day
    Maxicat 65ft Private Party Catamaran in Cartagena
    Sailing in Cartagena · 80 guests

    Maxicat 65ft Private Party Catamaran in Cartagena

    New
    Superowner
    $838/hour
    Punta Cana - FAMILY BOAT
    Sailing in Bávaro · 200 guests

    Punta Cana - FAMILY BOAT

    New
    $160/hour
    All-inclusive Luxury Shared Charter - Power Cat - St Martin
    Caribbean · 10 guests

    All-inclusive Luxury Shared Charter - Power Cat - St Martin

    New
    $419/day
    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

    Top Destinations Nearby

    Sailing Reviews in Caribbean

    1. DP

      Dawn

      Luxury 52 Catamaran With AC - Price include 2 People

      ⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!

    2. CT

      Cassie

      Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

      We had a great experience with Garth and Byron! They shared lots of fun information about the island and we had a great day of snorkeling and sailing. Would definitely recommend for a group of 6-8 versus jumping on a big boat with lots of people.

    3. RF

      Rachel

      Luxury Lagoon 50' Catamaran Charter In Grenada and The Grenadines

      We had a great experience, boat was beautiful and luxurious, crew was excellent, food and drink delicious. A great day out on the water for all ages!

    4. AW

      Alexis

      Private Charters In Simpson Bay or Philipsburg

      Anna & Scott were amazing hosting my group! We had a good time & they were so patient with us being that we had a large group.

    5. JR

      Janell

      Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

      Garth and Byron really made sure that we had a good time! I would definitely use them again when I come back to St Martin!

    6. Lisa

      Lisa

      Sailing live aboard Charter in Montego Bay, Jamaica

      It was my first time using the service and Chris was always available when I had a question. My clients had a great time.

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