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All listings in O‘ahu

Incredible sailboat rentals in O‘ahu, United States.

Page 1 of 226 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
$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🥇!

4.8
Superowner
Best of 2026
$185/hour
Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!
Tours in Honolulu · 6 guests

Private Sunset Sail on Luxury Yacht, see whales, dolphins, and turtles!

4.8
Superowner
Best of 2026
$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
Best of 2026
$185/hour
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
$299/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 2026
$400/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
Best of 2026
$185/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! 🥇

4.5
Superowner
Best of 2026
$185/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
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
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

5.0
$165/hour
ONE OF A KIND, trimaran swimming & sailing charter experience in Waikiki
Sailing in Honolulu · 6 guests

ONE OF A KIND, trimaran swimming & sailing charter experience in Waikiki

4.9
$250/hour
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
$250+/hour
43' Jeanneau Cruising Monohull Charter in Honolulu
Sailing in Honolulu · 6 guests

43' Jeanneau Cruising Monohull Charter in Honolulu

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

Scape 40' Sailing Catamaran Honolulu, Hawaii

5.0
$500+/hour
BYOB Private Waikīkī Catamaran Charters
Sailing in Honolulu · 35 guests

BYOB Private Waikīkī Catamaran Charters

5.0
$600+/hour
Sunset Cruise on Luxury Sailing Yacht in Waikiki
Sailing in Honolulu · 6 guests

Sunset Cruise on Luxury Sailing Yacht in Waikiki

5.0
$250/hour
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
$700/hour
Private Sailing Catamaran Waikiki – 48ft French Luxury Yacht
Sailing in Honolulu · 12 guests

Private Sailing Catamaran Waikiki – 48ft French Luxury Yacht

5.0
$500/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
Waikiki’s Premier Lagoon 420 Catamaran Experience For 12 Guests
Sailing in Honolulu · 12 guests

Waikiki’s Premier Lagoon 420 Catamaran Experience For 12 Guests

New
$350+/hour
Brand new 2022 Excess 12 - 39' Luxury Catamaran (Oahu only)
Sailing in Honolulu · 12 guests

Brand new 2022 Excess 12 - 39' Luxury Catamaran (Oahu only)

New
$660/hour
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$900/hour
Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 12 guests

Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii

5.0
$700/hour

Sailing Reviews in O‘ahu

  1. SH

    Sue

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

    What a great evening we had on the water, enjoying the views of Waikiki, Diamond Head, and the gorgeous sunset with Tony! Tony is a real interesting guy, with lots of stories from his vast experiences sailing all over the world. He is passionate about Hawaii and we thoroughly enjoyed chatting with him as we sailed. We are definitely glad that we chose Tony for this sunset cruise. I'm convinced it was the best choice we could have made.

  2. CD

    Ceri

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

    Had a brilliant day out with Tony on his boat. He’s very accommodating, great fun and he had lots of great info about the island. He lets you run your trip as you’d like and offers great suggestions on best places to snorkel and chill. I would highly recommend Tony and we’ll definitely go out again with him when we come back to Oahu

  3. EP

    Emma

    Epic 34' Catamaran Sailing in Waikiki

    Polu was very accommodating and friendly. He didn’t bother us, let us do our own thing. He asked us if we wanted to snorkel or just cruise around. We got to see so many dolphins and when we changed our mind and decided we wanted to snorkel he took us back to the snorkel location and gave us supplies to get into the water to see all the fish.

  4. AT

    Anna

    A Private sail, snorkeling adventure! Best of GetMyBoat 2021, 2022 and 2023🥇!

    A perfect sunset sail, the crew made us feel so safe and well taken care of. A few members of our party got a little sea sick and our captain immediately noticed and redirected to calmer waters. An amazing time!

  5. Rachel

    Rachel

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

    Tony created an amazing experience for all of us, the boat is beautiful, he was communicative and really experienced. He helped us have the best experience! Would definitely go back!

  6. Andrea

    Andrea

    Sunset Sails💥$295💥

    If you’re in Honolulu, this sailing charter is a must. Nothing compares to seeing the islands from the water. As we left the harbor, the views of Waikiki and Diamond Head were absolutely breathtaking—something you can’t fully appreciate from land. The 46-ft sloop was spotless and comfortable, and Captain Allen and his crew made sure we felt completely at ease. We booked this for a deeply meaningful occasion—spreading our loved one’s ashes—and it was a beautiful, respectful experience to honor her memory, that we’ll never forget. Highly recommend for anyone looking for something truly special.