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All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, United States.

Page 1 of 236 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 · 12 guests

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

5.0
Superowner
Best of 2023
$350hour
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
Superowner
Best of 2023
$185hour
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
Superowner
Best of 2023
$300hour
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
Superowner
Best of 2023
$185hour
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
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
Superowner
Best of 2023
$499hour
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
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

5.0
$165hour
One of a kind, exhilarating trimaran sailing experience in Waikiki
Sailing in Honolulu · 6 guests

One of a kind, exhilarating trimaran sailing experience in Waikiki

4.9
$75person
Scape 40' Sailing Catamaran Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500-$750hour
40ft Luxury Catamaran for Honolulu Adventures
Honolulu · 49 guests

40ft Luxury Catamaran for Honolulu Adventures

5.0
$650hour
Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!
Sailing in Honolulu · 33 guests

Custom 38ft Private Party 33 Passenger Gorgeous Catamaran!

5.0
$990hour
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
40ft sailing race yacht
Sailing in Honolulu · 6 guests

40ft sailing race yacht

New
$180hour
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
Waikiki Sunset Boat Charters and Custom Day Tours
Sailing in Honolulu · 8 guests

Waikiki Sunset Boat Charters and Custom Day Tours

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

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

New
$999hour

Top Destinations Nearby

Sailing Reviews in O‘ahu

  1. FR

    Frederick

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

    Tony communicated with me from the time of reservation and even after the cruise. He was on time, explained our cruise experience. And ensured we had an amazing time and memories. The boat was well maintained and equipped. Tony had snacks and beverages available. We cruised along the Waikiki coastline and took advantage of the beautiful scenery from the ocean. His ship mate Abe was very attentive and making sure our concerns were met. He took great pictures of us. He also was our guide during the snorkeling tour. We were able to se lots of fish and some turtles. Overall we had a great time and beautiful memories.

  2. DT

    Diana

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

    Tony is such an amazing captain, and we enjoyed every minute of our sailing trip! The boat is super well-kept, all the equipment is available onboard, your role is just to relax and enjoy! What we appreciated the most is how Tony cared about our safety due to the bad weather conditions: he proactively contacted us and found alternative sailing time that worked perfectly to everyone. Thank you for everything!

  3. joseph

    joseph

    40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

    Book with confidence!!! Great communication and the crew was phenomenal. Highly experienced on the ocean. We had a blast! We have some amazing memories and photos that will last a lifetime. Definitely will book with Captain Rob again. We booked out 5 months in advance which was no problem. Have a great sailing!

  4. KV

    Keara

    40' Beneteau Luxury Private Sailing Charter in Kewalo Basin Honolulu

    We had a wonderful time with Captains Rob and Tom! Good conversation, great company, and a beautiful boat and day on the water. Captain Tom even went above and beyond and we were able to see whales. Highly recommend for a great experience on a sailboat!

  5. PS

    Perry

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

    We had Captian Tom and Ken on our booking . Great value , We didn’t have time to grab drinks and snack/ sandwiches prior to sailing as the cab driver taking us to the marina did know where the supermarket was on the way . Ken was gracious enough to drive me to the closet store so we could enjoy the day. booked 4 hour trip and went snorkelling ( didn’t see much ) it was still great . then put the sails up and it was awesome to experience a sailboat for the first time andfortunate enough to see some whales up close (pretty cool ) Both Tom and Ken were excellent . remember to bring your own supplies for food. we were 7 in total and it was the right amount of people for this vessel . Thanks again Tom and Ken . wish you all the best !

  6. Ross

    Ross

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

    Great experience, very knowledgeable captain, capable boat. We had a great time and would recommend Tony to anyone looking for a fun cruise that is more personal than the crowded tour company boats.