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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 1 of 240 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
The best value Sunset Cruise off Waikiki! Beneteau 43ft.
Sailing in Honolulu · 12 guests

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

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 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
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
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
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
Instant Book
Honolulu Private Catamaran Sailing from Kewalo Harbor
Sailing in Honolulu · 49 guests

Honolulu Private Catamaran Sailing from Kewalo Harbor

New
$1,600/hour
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500+/hour
Instant Book
$100 Off Winter Sale! Private Luxury Charter in Honolulu on a 41' Japanese Sloop
Sailing in Honolulu · 6 guests

$100 Off Winter Sale! Private Luxury Charter in Honolulu on a 41' Japanese Sloop

New
$233+/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
Instant Book
Honolulu Private Morning Ceremony Sail Catamaran Charter Oahu, USA
Sailing in Honolulu · 49 guests

Honolulu Private Morning Ceremony Sail Catamaran Charter Oahu, USA

New
$1,117/hour
Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!
Sailing in Honolulu · 12 guests

Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!

New
$999/hour
Instant Book
49 tour, snorkel, whale watch catamaran
Events in Kula · 49 guests

49 tour, snorkel, whale watch catamaran

New
$1,700/hour
Sunset Boat Charters and Custom Day Tours with 28.5 Hunter Yacht
Sailing in Honolulu · 6 guests

Sunset Boat Charters and Custom Day Tours with 28.5 Hunter Yacht

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

Sailing Reviews in Hawaii

  1. Gersan

    Gersan

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

    Captain Tony made our proposal an absolutely magical experience! His kindness, professionalism, and warm personality set the perfect tone for our sunset sail, creating a moment we’ll cherish forever. From start to finish, he went above and beyond to make everything feel special, and we couldn’t have asked for a more perfect setting for such an important day.

  2. cc

    cristian

    Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull

    We spent an afternoon with the family and it was a wonderful experience sailing, with the sound of the sea and the wind. I believe that Keahi and his partner have made this experience something superior, we are very grateful for their hospitality.

  3. DO

    David

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

    These folks are pros. Steve has sailed all over the Pacific. From Hawaii, Tahiti, and LA. He knows boats inside and out. He and Savanna's goal from the outset was for us to have a superior experience. We saw a whale, turtles, and fish. Which for those of you are into that, they make every effort to accommodate. For me, however, the best part was the professional and relaxed approach. My wife had a bit of a gimpy leg and they helped her get around the boat. Great trip.

  4. GM

    Geraldine

    Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii

    My family and I had the best experience with Richie and his crew. The boat was beautiful and everyone had a great time. The crew was very friendly and very helpful. I would definitely recommend booking with them!

  5. DP

    Debra

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

    My friends and I booked an excursion with sale Hawaiian style last year, and it was definitely top of list to do again this year. We had such a great time and the captain and staff were so wonderful and so helpful. It was absolutely perfect and we can’t wait to see them again next year!

  6. SG

    Sue

    Epic 34' Catamaran Sailing in Waikiki

    This excursion was amazing! Captain Polu found a pod of dolphins that stayed with us for most of the voyage and gave us quite the show!