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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 1 of 234 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
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🥇!

5.0
Superowner
$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
$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
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 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
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
$175/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! 🥇

4.3
Superowner
$185/hour
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

New
$165/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
$200/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
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
Stunning Beneteau 42 Experience in Honolulu, Oahu
Sailing in Honolulu · 6 guests

Stunning Beneteau 42 Experience in Honolulu, Oahu

4.0
$1,550/day
Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht
Sailing in Honolulu · 6 guests

Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht

New
$1,800/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
Waikīkī’s Premier Catamaran Experience
Sailing in Honolulu · 12 guests

Waikīkī’s Premier Catamaran Experience

New
$350+/hour
50ft Hans Christian Yacht
Sailing in Honolulu · 6 guests

50ft Hans Christian Yacht

New
$199/hour
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$900/hour

Sailing Reviews in Hawaii

  1. KB

    Keith

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

    We had a great time. We enjoyed relaxing on the water seeing the sea life and Waikiki shoreline. The captain and his wife were on time, friendly, and full of information. I highly recommend this charter.

  2. Derricka

    Derricka

    Epic 34' Catamaran Sailing in Waikiki

    Great experience with it being my first time on a yacht! Captain was so accommodating and truly a great time!

  3. Ages

    Ages

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

    So amazing! Loved it so much, it was so beautiful, so peaceful and great to have the boat just for my husband and I. The most beautiful way to enjoy a sunset. Truly so romantic. Fellas I’m telling you, it’s worth it to splurge to be able to have your own boat for you and your significant other. Will definitely be booking again and will recommend to all of our friends who are visiting Oahu.

  4. KG

    Katy

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

    What a WONDERFUL day! The snorkeling was even better because Savannah and Whitney had us buttoned up on exactly how to see the best spots. Our Captain, Tom was the perfect blend with Savannah and Whitney. The boat was perfect for all of us. We were very comfortable with 10 people. I highly recommend both the boat AND the crew!

  5. TF

    Teresa

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

    This was the best charger we have been on! The staff were exceptional and the boat was fantastic! We had such a great time! Thank you, Bella, Savannah, and CPT George!

  6. RW

    Rachel

    Epic 34' Catamaran Sailing in Waikiki

    Our trip with captain Polu was so much fun! Super easy to communicate and book. Lots of room on boat, clean, and he was very flexible with where we wanted to go and what we wanted to do. He provided an ice chest, snorkel equipment, floaties, and a speaker!