Cookies!

We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.

All listings in Honolulu

Great sailboat rentals near Honolulu, Hawaii.

Page 1 of 235 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
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
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 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 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
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
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
Waikiki Sunset Boat Charters and Custom Day Tours
Sailing in Honolulu · 6 guests

Waikiki Sunset Boat Charters and Custom Day Tours

5.0
$250/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
***99.00/ person/hr ***COME SAIL THE DREAM ON OUR LUXURY 52 ft SAILING YACHT***
Sailing in Honolulu · 12 guests

***99.00/ person/hr ***COME SAIL THE DREAM ON OUR LUXURY 52 ft SAILING YACHT***

5.0
$99/hour
Blue water Hawaiian Sailboat Cruise with USCG Licensed 100 Ton Captain
Sailing in Honolulu · 4 guests

Blue water Hawaiian Sailboat Cruise with USCG Licensed 100 Ton Captain

New
$150/hour
Instant Book
The SV Praha Luxury Sailing Yacht in Honolulu, Hawaii
Sailing in Honolulu · 6 guests

The SV Praha Luxury Sailing Yacht in Honolulu, Hawaii

5.0
$388/hour
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$1,500/hour
27ft Classic Sailboat
Sailing in Honolulu · 6 guests

27ft Classic Sailboat

New
$199/hour

Top Destinations Nearby

Sailing Reviews in Honolulu

  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. 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.

  3. 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!

  4. 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!

  5. JC

    Jodee

    Epic 34' Catamaran Sailing in Waikiki

    We had the best time with Captain Polu! Was so nice having the boat to ourselves and we got to see a lot of sea life and truly enjoyed our time. Wish we had done the ride longer! I highly recommend this

  6. JG

    John

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

    Fantastic family outing. We brought poke and drinks on board for a 3 hour sunset cruise and snorkel. Our kids saw turtles and we had a great relaxing time. Enjoyed the trip and the company. Tony and Quinn were welcoming and shared their experiences from life. Thanks for providing exactly what I was looking for.