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All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, 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
$180hour
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 2023
$185hour
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
Best of 2023
$99person
Private sailing on Beneteau 43' Luxury Yacht! GetMyBoat 2021 & 2022 Winner! 🥇
Sailing in Honolulu · 12 guests

Private sailing on Beneteau 43' Luxury Yacht! GetMyBoat 2021 & 2022 Winner! 🥇

4.9
Superowner
Best of 2023
$185hour
The best value Sunset Cruise off Waikiki! Beneteau 43ft.
Sailing in Honolulu · 12 guests

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

4.9
Superowner
Best of 2023
$185hour
Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
Sailing in Honolulu · 6 guests

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

5.0
Superowner
Best of 2023
$350hour
Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks
Sailing in Honolulu · 12 guests

Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks

5.0
Best of 2023
$149person
Diamond Head Sunset Sail on Private 43' Luxury Yacht! Book Now!
Sailing in Honolulu · 12 guests

Diamond Head Sunset Sail on Private 43' Luxury Yacht! Book Now!

5.0
Best of 2023
$89person
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
Best of 2023
$99person
Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!
Sailing in Honolulu · 12 guests

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

New
$999hour
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
$650hour
Adventure Awaits on Private Luxury 50' Yacht for the Ultimate Sailing Experience
Sailing in Honolulu · 12 guests

Adventure Awaits on Private Luxury 50' Yacht for the Ultimate Sailing Experience

5.0
Best of 2023
$499hour
The best sunset sail! Very private! Best of GetMyBoat 2021 and 2022 Winner! 🥇
Sailing in Honolulu · 12 guests

The best sunset sail! Very private! Best of GetMyBoat 2021 and 2022 Winner! 🥇

4.2
Superowner
Best of 2023
$185hour
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
$235hour
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
$200hour
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

5.0
$165hour
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500-$750hour
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
$100-$300hour
Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!
Sailing in Honolulu · 33 guests

Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!

5.0
$990hour
Waikiki Sunset Boat Charters and Custom Day Tours
Sailing in Honolulu · 6 guests

Waikiki Sunset Boat Charters and Custom Day Tours

5.0
$99person
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
$700hour
Stunning Beneteau 42 Experience in Honolulu, Oahu
Sailing in Honolulu · 6 guests

Stunning Beneteau 42 Experience in Honolulu, Oahu

4.0
$1,550day
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$1,500hour
Best Sunset Cruise 50' Luxury Private Yacht. Book your sunset cruise today!
Sailing in Honolulu · 12 guests

Best Sunset Cruise 50' Luxury Private Yacht. Book your sunset cruise today!

New
Best of 2023
$499hour

Top Destinations Nearby

Sailing Reviews in O‘ahu

  1. SW

    Susana

    Hawaii's Best Waikiki Sail Snorkel Adventure Sunset Cruise Friday Nite Fireworks

    We booked the yacht as part of a bachelorette trip for a party of 7 and it was perfect! Everything on the yacht is as described on the listing. Captain and assistant were super accommodating and adjusted their schedule for us due to a last minute change on our end, which we greatly appreciated. Bring all the booze and snacks!

  2. RM

    Ryan

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

    We had such a great trip! Captain Steve and Savannah were great in providing a memorable trip. We were 4 adults an2 kids so we had plenty of space to relax while sailing around. They brought us to a great swim spot and made sure we were safe and having the best time. Can't wait to come back!

  3. FM

    Frankie

    Epic 34' Catamaran Sailing in Waikiki

    We had a total blast. Capitan Polu was the BEST! We felt at home on the boat. We saw sea turtles and enjoyed having a semi-private experience. We went to the same place as all of the big snorkeling tours, but we didn’t have to share a boat with 30 others. Highly recommend!

  4. HA

    HIROSHI

    40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

    We entrusted a company called Hawaii Sea burial Center, located in Tokyo, and came from Japan to Hawaii for an ocean scattering ceremony at Waikiki. With the performance of a ukulele player, it became a touching ceremony. The captain's service was excellent, and I thought that when I pass away, I would like my family to scatter my ashes from this yacht. Thank you.

  5. Ankit

    Ankit

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

    We had a great time with Tony. His boat is great and we were well taken care of. For a family of 6, this boat trip was a better value for money than doing a regular catamaran - this was more personal (only our family was onboard) and we could take our time snorkeling (being novices). It's a great way to do your own thing, at your own pace, at your own time!

  6. Ginger

    Ginger

    Epic 34' Catamaran Sailing in Waikiki

    I can’t recommend Captain Polu enough!!! The boat was perfect for our group of 10. We all had an amazing time. We weren’t really sure where to go out in the water but he took us out right in front of Waikiki strip and the views were great! Any time I had a question I was able to text him and he gave me an answer right away!