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    All listings in Hawaii

    Incredible sailboat rentals in Hawaii, United States.

    4.9
    (1,122 Reviews)

    Page 1 of 2 • 33 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling
    Sailing in Honolulu · 6 guests

    Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

    5.0
    Best of 2025
    $180/hour
    A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!
    Sailing in Honolulu · 12 guests

    A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!

    4.8
    Superowner
    $185/hour
    Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!
    Tours in Honolulu · 6 guests

    Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!

    4.8
    Superowner
    $185/hour
    Instant Book
    40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu
    Sailing in Honolulu · 12 guests

    40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

    4.8
    Superowner
    $185/hour
    Epic 34' Catamaran Sailing in Waikiki
    Sailing in Honolulu · 12 guests

    Epic 34' Catamaran Sailing in Waikiki

    5.0
    Superowner
    $299/hour
    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
    Sailing in Honolulu · 15 guests

    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    5.0
    Superowner
    Best of 2025
    $400/hour
    Private sail on Luxury 43' Yacht! Best of GetMyBoat 2021, 2022, and 2023! 🥇
    Sailing in Honolulu · 12 guests

    Private sail on Luxury 43' Yacht! Best of GetMyBoat 2021, 2022, and 2023! 🥇

    4.9
    Superowner
    $185/hour
    Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull
    Sailing in Maalaea · 6 guests

    Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull

    5.0
    Superowner
    $475/hour
    The best sunset sail! Very private! Best of GetMyBoat 2021, 2022 and 2023! 🥇
    Sailing in Honolulu · 12 guests

    The best sunset sail! Very private! Best of GetMyBoat 2021, 2022 and 2023! 🥇

    4.4
    Superowner
    $185/hour
    Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii
    Sailing in Honolulu · 30 guests

    Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii

    5.0
    $650/hour
    42 ft Beneteau, located in Kewalo Basin, 2 miles from Waikiki.
    Sailing in Honolulu · 6 guests

    42 ft Beneteau, located in Kewalo Basin, 2 miles from Waikiki.

    5.0
    $235/hour
    ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki
    Sailing in Honolulu · 6 guests

    ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki

    4.9
    $250/hour
    43' Jeanneau Cruising Monohull Charter in Honolulu
    Sailing in Honolulu · 6 guests

    43' Jeanneau Cruising Monohull Charter in Honolulu

    5.0
    $165/hour
    Sunset Cruise on Luxury Sailing Yacht in Waikiki
    Sailing in Honolulu · 6 guests

    Sunset Cruise on Luxury Sailing Yacht in Waikiki

    5.0
    $550/hour
    Scape 40' Sailing Catamaran Honolulu, Hawaii
    Sailing in Honolulu · 12 guests

    Scape 40' Sailing Catamaran Honolulu, Hawaii

    5.0
    $500+/hour
    41ft Smooth Sailing Trimaran Charters & Adventures Oahu's North Shore, Haleiwa
    Sailing in Haleiwa · 6 guests

    41ft Smooth Sailing Trimaran Charters & Adventures Oahu's North Shore, Haleiwa

    5.0
    $250+/hour
    BYOB Private Waikīkī Catamaran Charters
    Sailing in Honolulu · 35 guests

    BYOB Private Waikīkī Catamaran Charters

    5.0
    $600+/hour
    Largest, most luxurious sailing catamaran on the island of Oahu
    Events in Honolulu · 12 guests

    Largest, most luxurious sailing catamaran on the island of Oahu

    5.0
    $1,119+/hour
    46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii
    Sailing in Kapolei · 6 guests

    46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii

    5.0
    $700/hour
    Adventures aboard 48' Luxury Catamaran
    Sailing in Waianae · 12 guests

    Adventures aboard 48' Luxury Catamaran

    5.0
    $700/hour
    Sunset Sails💥$295💥
    Sailing in Honolulu · 6 guests

    Sunset Sails💥$295💥

    New
    $165/hour
    Stunning Beneteau 42 Experience in Honolulu, Oahu
    Sailing in Honolulu · 6 guests

    Stunning Beneteau 42 Experience in Honolulu, Oahu

    4.0
    $1,550/day
    Sunreef 62 catamaran
    Sailing in Maalaea · 12 guests

    Sunreef 62 catamaran

    New
    $1,200/hour
    Maui, private 49 tour, snorkel, whale watch catamaran
    Events in Kula · 49 guests

    Maui, private 49 tour, snorkel, whale watch catamaran

    New
    $1,950/hour

    Top Destinations Nearby

    Sailing Reviews in Hawaii

    1. KL

      Katheryne

      A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!

      Captain Rob was helpful answering all my questions. Captain Joseph and Kenny were very kind and empathetic. We booked the trip to spread our mom's ashes, and they were so respectful and kind. They even gave us a few laughs during a difficult time. They also gave us free water bottles. We really appreciated them! <3 Thanks you guys.

    2. BP

      Benedict

      A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!

      Captain Joseph was incredibly laid-back and our group had really fun conversations with him throughout the entire trip. He was super communicative to our group at the start and continued to do so throughout. Boat size was good for our group of 10 and AMAZING sunset and city views!! Unforgettable experience

    3. WS

      Wendy

      Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

      Experience Hawaii in a whole new way by taking a sailing trip with Tony. It was a perfect way for our family and friends to celebrate a birthday. The wind was up, the water was beautiful and the sights were amazing. Everything was safe, seamless and fun! Highly recommend it for anyone looking for a sailing adventure. And Tony is a great master of ceremony!

    4. TS

      Taylor

      ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki

      Kiah and Alec were amazing!! They made sure we had the best time on our girls day. Everything went exactly as planned, the boat was the perfect size, and you really couldn’t want for anything else. I cannot recommend them enough!

    5. Jessica

      Jessica

      Epic 34' Catamaran Sailing in Waikiki

      Amazing time for our bachelorette group of 7! Captain was respectful, knowledgeable, chill and awesome. We had such a fun time.

    6. Shane

      Shane

      Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

      Tony is great. If you really are a sailor he knows what to expect, it was a great experience.

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