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$100-$300
All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, United States.

Page 1 of 114 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
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
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
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 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
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
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
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
$200hour
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
Vintage Sailing Yacht in Honolulu! Private Luxury Sail + Swim Tours
Sailing in Honolulu · 6 guests

Vintage Sailing Yacht in Honolulu! Private Luxury Sail + Swim Tours

New
$300hour

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Sailing Reviews in O‘ahu

  1. Brittany

    Brittany

    One of a kind, exhilarating trimaran sailing experience in Waikiki

    This was an absolutely amazing and breathtaking private boat ride in celebration of my husband’s birthday. The communication was superb! Kiah responded to all of my inquiries quickly and kindly and everything was just as described. Not to mention, the crew had such great personalities, were a lot of fun and definitely empowered us to personalize our ride the way we wanted. I truly couldn’t have made a better choice on this booking and when I return to Hawai’i, she will be my first call! I highly, highly recommend!

  2. ME

    Meagan

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

    I cannot say it enough - BOOK your time with Captain Tony! We had the most incredible experience start to finish. The dock & slip were easy to find, communication beforehand was great, & Tony & Olan were really helpful & inviting. Though it rained at first for a few minutes, it cleared up right away & we got to see DOLPHINS up close to the boat!! The wind picked up & we were able to truly sail & then we got to see WHALES coming up to the surface near the boat (this was in April, even after whale season, so a totally unexpected surprise)! After we sailed for a while, we anchored & used the onboard snorkeling equipment to check out a quiet reef area where were the only boat around. We felt very safe & enjoyed every moment - Tony even had a speaker for us to bluetooth our favorite music. The boat is absolutely big enough for 6, and we were able to bring drinks and food to enjoy on our afternoon. We sailed for 4 hours and truly could have extended our time onboard if we had more time. I would absolutely recommend this experience to anyone - couples, friends, family - you won’t regret it. We’ll be back!!

  3. 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.

  4. 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!

  5. 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!

  6. 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!