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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
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
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
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
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
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 experience in Waikiki
Sailing in Honolulu · 6 guests

One of a kind, exhilarating trimaran sailing 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
40ft Luxury Catamaran for Honolulu Adventures
Honolulu · 49 guests

40ft Luxury Catamaran for Honolulu Adventures

5.0
$650hour
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 · 8 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
40ft sailing race yacht
Sailing in Honolulu · 6 guests

40ft sailing race yacht

New
$180hour
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
$388hour

Top Destinations Nearby

Sailing Reviews in O‘ahu

  1. JK

    Jaci

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

    We'd definitely recommend Captains Tom & Rob! This was our first sailing adventure and my in-laws' first ever time out on the ocean! Captain Tom and Johnny were patient, helpful and made sure everyone felt safe and had fun. We enjoyed the sail to Diamondhead and back (even with high winds!) and a chance to snorkel away from the tourist crowds. It allowed my in-laws to feel more comfortable and confident about getting in the water - and they were so happy they did! We're looking forward to doing this again with future visitors.

  2. SR

    Steven

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

    Amazon crew. The prices have to be the best on the island, the experience is exactly what you are looking for. We chartered for 3 hours and wanted the sunset at the end. The PRIVATE experience is great for families looking to spend time together without other tourist with you.

  3. 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!

  4. 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!!

  5. Sean

    Sean

    Epic 34' Catamaran Sailing in Waikiki

    Captain Polu is a true Hawaiian... warm, friendly, relaxed and a great captain. Celebrated an 80th birthday with a short cruise and snorkel on a what turned out to be a beautiful day. Great boat with lots of indoor shade as well as a place to relax in front. Felt like we more than got our money's worth. Thank you again and mahalo, Captain Polu!

  6. 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.