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    All listings in Caribbean

    Awesome sailboat rentals in the Caribbean.

    4.8
    (2,100 Reviews)

    Page 3 of 16 • 381 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico
    Sailing in San Juan · 6 guests

    Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

    4.9
    Superowner
    $198/hour
    Instant Book
    ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.
    Sailing in Miami · 4 guests

    ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.

    5.0
    Superowner
    $75+/hour
    Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
    Sailing in Miami Beach · 42 guests

    Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

    4.7
    Superowner
    Best of 2025
    $800/hour
    Sunset Sail in Bay of Santa Marta, Magdalena
    Sailing in Comuna 2 · 12 guests

    Sunset Sail in Bay of Santa Marta, Magdalena

    5.0
    $125/hour
    Instant Book
    “Exclusive Escape, Unlimited Adventure on our Yacht”
    Events in Miami · 14 guests

    “Exclusive Escape, Unlimited Adventure on our Yacht”

    5.0
    $250/hour
    Instant Book
    Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island
    Tours in Fajardo · 6 guests

    Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

    5.0
    Superowner
    Best of 2025
    $1,500/day
    Luxury Private Catamaran Charter – All-Inclusive from St. Maarten
    Sailing in Cole Bay · 16 guests

    Luxury Private Catamaran Charter – All-Inclusive from St. Maarten

    5.0
    $2,095/day
    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
    Sailing in Nassau · 40 guests

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    5.0
    Best of 2025
    $960/hour
    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR
    Events in Bávaro · 60 guests

    🏆Best Boat 2025🏆 Private Boat 3H with Unlimited drinks and Sand-bar in DR

    New
    $184+/hour
    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
    Sailing in Miami · 13 guests

    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

    5.0
    $187+/hour
    Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
    Sailing in Cartagena · 45 guests

    Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

    4.9
    Superowner
    Best of 2025
    $300/hour
    Charter Beneteau Oceanis 440 in Saint Lucia private sailing cruise
    Sailing in Gros Islet · 9 guests

    Charter Beneteau Oceanis 440 in Saint Lucia private sailing cruise

    5.0
    $1,118/day
    Luxury Lagoon 440 Sailing Catamaran in Key West
    Sailing in Key West · 6 guests

    Luxury Lagoon 440 Sailing Catamaran in Key West

    5.0
    $250/hour
    Sailing Catamaran Yacht for up to 24 Guests in Aruba
    Sailing in Oranjestad-West · 24 guests

    Sailing Catamaran Yacht for up to 24 Guests in Aruba

    4.6
    Superowner
    Best of 2025
    $600/hour
    Instant Book
    Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
    Powerboats in Fort Lauderdale · 6 guests

    Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

    4.8
    Superowner
    $113+/hour
    Instant Book
    Discover Miami on this Sea Ray Yacht Charter
    Events in Miami · 12 guests

    Discover Miami on this Sea Ray Yacht Charter

    5.0
    $100/hour
    sunbathe and relax on our island in the middle of the ocean
    Events in Punta Cana · 100 guests

    sunbathe and relax on our island in the middle of the ocean

    3.7
    Superowner
    Best of 2025
    $50/hour
    Let's go Sailing in Miami!
    Sailing in Miami · 6 guests

    Let's go Sailing in Miami!

    5.0
    $45+/hour
    Instant Book
    46' Oyster Sailboat in St. Thomas, Virgin Islands
    Sailing in St. Thomas · 6 guests

    46' Oyster Sailboat in St. Thomas, Virgin Islands

    5.0
    $197+/hour
    🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
    Events in Sosúa · 150 guests

    🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

    5.0
    $425/hour
    🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
    Events in Sosúa · 150 guests

    🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

    4.4
    $300/hour
    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
    Sailing in Collectivity of Saint Martin · 12 guests

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    4.9
    $1,153/day
    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
    Sailing in Cartagena · 23 guests

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    4.9
    $1,650/day
    Sailing From Pompano Beach, FL - $200/Hour - $33.33/Person
    Sailing in Pompano Beach · 12 guests

    Sailing From Pompano Beach, FL - $200/Hour - $33.33/Person

    4.5
    Superowner
    $125+/hour

    Sailing Reviews in Caribbean

    1. AB

      Afolabi

      “Exclusive Escape, Unlimited Adventure on our Yacht”

      This trip was top class a 10/10 , very respectful captain, good communication and professionalism at its highest . Really appreciate Carlos and the captain.

    2. AF

      Angela

      Sailing Catamaran Yacht for up to 24 Guests in Aruba

      Book it!! Hands down the best crew ever! I had a group of 18 and everyone enjoyed themselves. The crew is very attentive and entertaining. I would highly recommend them. Thanks again guys!!!

    3. RI

      Robert

      “Exclusive Escape, Unlimited Adventure on our Yacht”

      Had a great time on the boat, wonderful experience, the sound system is very very nice and the captain was great too. Overall great experience and hope to do it again soon!!

    4. JE

      Jackie

      “Exclusive Escape, Unlimited Adventure on our Yacht”

      Truly had the best time with the crew and on the boat. Booking went so smoothly and the crew gave us the best time celebrating our bride. Will book with them again in the future!

    5. SK

      Sandy

      Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

      If you are looking for an authentic sailing experience in Puerto Rico, look no further. This is for you! We came in with sailing experience but not in the ocean and not on as large of a boat. He let us sail the entire time and taught us along the way. Jimbo is a very experienced sailor and is looking to give you the sailing experience you are looking for. If I could have given him more than 5 stars I would have!

    6. FS

      Felicia

      Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

      This experience was amazing! This was the first time my family experienced a sunset ride on a sailboat and Jimbo made sure the experience was one we'd always remember. Jimbo ensured we were in the know on all safety protocols and during the sail, enlightened us with facts and history about Puerto Rico. Jimbo was personable and accommodating from the beginning to end of our excursion. This was our first, but not our last trip with Jimbo!

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