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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

4.9(Average of 1,084 reviews in this area)
Page 1 of 2 (42 listings)
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
$180hour
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
Best of 2023
$99person
Private Sailing Charter only people in your party, no other people! Luxury 40 Ft Beneteau. Best of GetMyBoat 2021 and 2022 Winner! 🥇 Sail Away in Paradise! Kewalo Basin Honolulu
Sailing in Honolulu · 12 guests

Private Sailing Charter only people in your party, no other people! Luxury 40 Ft Beneteau. Best of GetMyBoat 2021 and 2022 Winner! 🥇 Sail Away in Paradise! Kewalo Basin Honolulu

4.8
Superowner
Best of 2023
$185hour
Have an exciting Very Private sailing adventure on a  Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!
Sailing in Honolulu · 12 guests

Have an exciting Very Private sailing adventure on a Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!

4.9
Superowner
Best of 2023
$185hour
Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
Sailing in Honolulu · 12 guests

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

5.0
Superowner
Best of 2023
$350hour
Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks
Sailing in Honolulu · 12 guests

Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks

5.0
Superowner
Best of 2023
$300hour
The best value Sunset Cruise off Waikiki! Beneteau 43ft.
Sailing in Honolulu · 12 guests

The best value Sunset Cruise off Waikiki! Beneteau 43ft.

4.9
Superowner
Best of 2023
$185hour
Diamond Head Sunset Sail on Private 43' Luxury Yacht! Book Now!
Sailing in Honolulu · 12 guests

Diamond Head Sunset Sail on Private 43' Luxury Yacht! Book Now!

5.0
Superowner
Best of 2023
$185hour
Hawaii's Best Waikiki Sail and Coral Garden Snorkeling Adventure. Book Now!
Sailing in Honolulu · 12 guests

Hawaii's Best Waikiki Sail and Coral Garden Snorkeling Adventure. Book Now!

4.9
Superowner
Best of 2023
$185hour
Sailing and Snorkeling Adventures in Lahaina, Hawaii on 36 Foot Lidgard Monohull
Sailing in Lahaina · 6 guests

Sailing and Snorkeling Adventures in Lahaina, Hawaii on 36 Foot Lidgard Monohull

5.0
Superowner
$475hour
Adventure Awaits on Private Luxury 50' Yacht for the Ultimate Sailing Experience
Sailing in Honolulu · 12 guests

Adventure Awaits on Private Luxury 50' Yacht for the Ultimate Sailing Experience

5.0
Superowner
Best of 2023
$499hour
The best sunset sail! Very private! Best of GetMyBoat 2021 and 2022 Winner! 🥇
Sailing in Honolulu · 12 guests

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

4.2
Superowner
Best of 2023
$185hour
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
$650hour
Spacious Sailing Trimaran in Honolulu, Hawaii
Sailing in Honolulu · 45 guests

Spacious Sailing Trimaran in Honolulu, Hawaii

5.0
$750hour
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
$235hour
One of a kind, exhilarating trimaran sailing experience in Waikiki
Sailing in Honolulu · 6 guests

One of a kind, exhilarating trimaran sailing experience in Waikiki

4.9
$75person
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

5.0
$165hour
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500-$750hour
40ft Luxury Catamaran for Honolulu Adventures
Honolulu · 49 guests

40ft Luxury Catamaran for Honolulu Adventures

5.0
$650hour
Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!
Sailing in Honolulu · 33 guests

Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!

5.0
$990hour
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
$100-$300hour
Fountaine Pajot 46 catamaran
Sailing in Maalaea · 12 guests

Fountaine Pajot 46 catamaran

New
$965hour
Waikiki boat charters
Sailing in Honolulu · 8 guests

Waikiki boat charters

5.0
Snoozed - Active 08 May 2024
Stunning Beneteau 42 Experience in Honolulu, Oahu
Sailing in Honolulu · 6 guests

Stunning Beneteau 42 Experience in Honolulu, Oahu

4.0
$1,550day

Sailing Reviews in Hawaii

  1. sa
    shaman
    Sailing and Snorkeling Adventures in Lahaina, Hawaii on 36 Foot Lidgard Monohull

    The service and the communication was amazing I felt very special like my desires were met. I saw that the captain went out of his way to make sure we were happy. 😃 I do not write reviews but I will for them. Thanks for a gift and experience I will not forget .

  2. PB
    Powell
    Private sailing on 45 foot Luxury yacht ,day sailing, sunset sail ,snorkeling

    Captain Tony is the best! He really made our trip out to Hawaii a dream. I was proposing to my girlfriend and he set everything up to make it magical. I can’t rave enough about Captain Tony so if you’re looking to book a boat, definitely book here!

  3. EN
    Elizabeth
    Have an exciting Very Private sailing adventure on a Beneteau 43 Foot Luxury Yacht! Best of GetMyBoat 2021 and 2022 Winner! 🥇! Sail Away in Paradise! Kewalo Basin Honolulu!

    Second time sailing with this crew and it was just as amazing as the first! We asked for sailing, swimming, and whale watching and Captain Tom didn’t disappoint. Thank you for making my husbands birthday a memorable one.

  4. MF
    Mikaela
    Private sailing on 45 foot Luxury yacht ,day sailing, sunset sail ,snorkeling

    We had an amazing day on the water with Captain Tony, we didn’t want it to end! The boat was clean and well kept, and Captain was very amicable and knowledgeable. He was very flexible in letting us expand and extend our trip which we greatly appreciated. I highly recommend booking with him.

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

    Tom and Savannah were an awesome crew for our group of 7. Both were very knowledgeable about the area we cruised, Savannah led the snorkel and helped our family have a great experience with the fish and turtles, made several sweet videos of the snorkeling and showed our adult kids how to dive down. Overall safety on the boat and desire for all of us to have a great experience were at the forefront. When Captain Tom was made aware of a pod of dolphins close by, he helped us see the beautiful creatures. We had time to swim, relax and enjoy the lunch we had delivered to the boat prior to departure. Thank so much!

  6. DA
    Dani
    Epic 34' Catamaran Sailing in Waikiki

    Captain Polu was very knowledgeable and an awesome captain. We had a great time snorkeling and laying out on the catamaran!