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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 1 of 230 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
$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
Best of 2026
$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
Best of 2026
$185/hour
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
Best of 2026
$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 2026
$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
Best of 2026
$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
$525/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! 🥇

4.5
Superowner
Best of 2026
$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, trimaran swimming & sailing charter experience in Waikiki
Sailing in Honolulu · 6 guests

ONE OF A KIND, trimaran swimming & sailing charter 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
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500+/hour
BYOB Private Waikīkī Catamaran Charters
Sailing in Honolulu · 35 guests

BYOB Private Waikīkī Catamaran Charters

5.0
$600+/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
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
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
Private Sailing Catamaran Waikiki – 48ft French Luxury Yacht
Sailing in Honolulu · 12 guests

Private Sailing Catamaran Waikiki – 48ft French Luxury Yacht

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
Waikīkī’s Premier Catamaran Experience
Sailing in Honolulu · 12 guests

Waikīkī’s Premier Catamaran Experience

New
$350+/hour

Sailing Reviews in Hawaii

  1. TH

    Tammy

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

    We had such a great time on the boat! We saw whales, dolphins and turtles. Captain J and Kenny made sure we were safe and having fun. Professional yet laid back. It was fun jumping into the ocean off the boat!

  2. JH

    Jenn

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

    We had a great day with Tony- did some snorkeling, swimming and sailing. Can’t think of a better way to spend a few hours. Tony was super knowledgeable and had everything we could have needed for a fun day on the water.

  3. Cole

    Cole

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

    Absolutely phenomenal experience. The captain ran a tight, professional operation while keeping the energy high and the vibe relaxed. From departure to docking, everything was smooth, well-coordinated, and clearly delivered by someone who knows the water and knows how to host. The route was stunning, captain made everyone on board feel taken care of. If you’re looking for a tour that overdelivers on value, atmosphere, and overall execution, this is it. Five stars. would book again without hesitation.

  4. DC

    Danielle

    40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

    We had a nice time out with Captain Joseph and Kenny! They were both kind, helpful and fun! Definitely recommend! Beautiful scenic views

  5. JB

    Jamie

    Epic 34' Catamaran Sailing in Waikiki

    Great boat and a super chill experience. Polu does a great job communicating and making sure we have the day we wanted.

  6. CC

    Candance

    Epic 34' Catamaran Sailing in Waikiki

    Captain Polu is super knowledgeable and made for a very comfortable sail! He was very attentive to what we desired and modified accordingly (if needed). We would 10/10 recommend him!