Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 1 of 233 listings

 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🥇!

5.0
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!

4.9
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
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
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
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
Limited Availability
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
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
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
Instant Book
Adventures aboard 48' Luxury Catamaran
Sailing in Waianae · 12 guests

Adventures aboard 48' Luxury Catamaran

5.0
$450+/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
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
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

Sailing Reviews in Hawaii

  1. CP

    Carrie

    Epic 34' Catamaran Sailing in Waikiki

    Captain Polu was very accommodating and personable. We had a great time..enjoyed relaxing on the boat, seeing the sea life and the Waikiki shoreline. Also, enjoyed getting out on the water to swim and snorkel!

  2. Wendy

    Wendy

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

    Incredible Fireworks Boat Ride in Waikiki! We had such an amazing time on our Waikiki boat ride to see the Friday night fireworks! From the moment we boarded, the crew made us feel so welcome and comfortable. The boat was spacious, clean, and offered fantastic views of the Honolulu skyline. As we cruised along the shoreline, we got to enjoy the warm evening breeze, the twinkling city lights, and a picture-perfect view of Diamond Head. When the fireworks began, it was absolutely magical! Watching the show from the water—without the crowds—felt like having front-row seats at our own private celebration. The atmosphere was fun and relaxed, and plenty of opportunities for photos. It was one of the most memorable experiences of our trip, and I’d highly recommend it to anyone visiting Waikiki. Whether you’re with family, friends, or on a romantic evening, this boat ride is a must-do! 🌺🌊🎆

  3. ML

    Maggie

    Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull

    The staff at Gung Honsailing was wonderful. They accommodated me last minute and did everything to make the scattering of my dad’s ashes meaningful and respectful. They were incredibly caring when I became seasick, and super friendly and knowledgeable on our journey. I recommend them!

  4. Rich

    Rich

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

    We had a great sail with the team. Sunset cruise for my wife’s birthday. The captain and crew were spectacular and so nice. They made it a wonderful experience in a beautiful setting. Could not ask for better.

  5. AP

    Andy

    Largest, most luxurious sailing catamaran on the island of Oahu

    Trevor was an incredible captain, and his team went above and beyond to make sure our family had the best time on the water. Great communication, preparation, and all the best food, drinks, and fun! We will be back!

  6. AH

    Angelique

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

    We had a great time- Tom and Savannah were awesome and Ashley was super flexible with us when we had a flight delay. Highly recommend!