Incredible sailboat rentals in Hawaii, United States.

Average of 107 reviews in this area.
1 - 18 of 25 listings
25 results

Rent or charter a sailboat for a memorable experience in Hawaii.

Are you ready for a fun adventure out on the open water onboard a sailboat in Hawaii? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Hawaii is a wonderful sailboat rental destination.

Using GetMyBoat to book your next sailing experience.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sailing in Hawaii.

  1. TJ
    Troy
    Enjoy "Gauguin" Beneteau First 42.7 Monohull Charter in Honolulu, Hawaii

    Captain Mike & Michele were outstanding nautical hosts for our family outing. The booking and cruise around Waikiki were very professional and personalized to suit our family. This team made a great outing into a magical memory that our family will always cherish! Thanks again Captain Mike & Michele you are best sailing company in Oahu!

  2. HH
    Hassan
    Enjoy "Gauguin" Beneteau First 42.7 Monohull Charter in Honolulu, Hawaii

    We had a wonderful time with Captain Rick and Michele sailing for 5 hours. We got close to diamond head, then stopped for snorkeling and went on to stop at a tiki bar then ended with night sailing back to the marina. We dodnt get to see much marine life but we still caught some flying fish and some gorgeous rainbow. The crew is highly recommended as they will take care of yoi make sure youre comforable regardless of the conditions.

  3. RN
    Roni
    Sailing Charter On 40ft "Kahala Kai" Cruising Catamaran In Honolulu, Hawaii

    The crew was super accommodating and nice. The price was right compared to other booze cruises I've been on. I like how they provided a cooler with ice and water. We had a great time, even with the water being choppy. Thanks Captain Mike and Michele!

  4. ci
    cindy
    Royal Hawaiian Catamaran Charter in Honolulu

    Captain Richie his crew was awesome they were very nice and helpful, and service was superb, also Michelle was amazing she was keeping in touch with me the whole time building me and assuring me. This was an awesome experience highly recommend!

  5. SW
    Shari
    Sailing Charter On 40ft "Kahala Kai" Cruising Catamaran In Honolulu, Hawaii

    If you want a good time, book this boat with Captain Krash! I had a group of 14 and we had SUCH an amazing time. I will definitely book them again and recommend them to others!

  6. RZ
    ROBERTA
    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    Our party of 8 had an amazing day and evening onboard. We were able to swim with sea turtles at turtle canyon and sail around by Waikiki beach and diamond head. We would have gone farther but the wind and waves were too high to go past the point. Nevertheless it was a beautiful day and we also enjoyed the sunset. The vessel had snorkel equipment and a dining area with benches or nets to lounge on as well as a few bean bag chairs. The captain and first mate were knowledgeable and friendly during our 4 hours aboard. Definitely a highlight of our trip.