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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 1 of 229 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
Epic 34' Catamaran Sailing in Waikiki
Sailing in Honolulu · 12 guests

Epic 34' Catamaran Sailing in Waikiki

5.0
Superowner
$299/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
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 and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull
Sailing in Maalaea · 6 guests

Sailing and Snorkeling Adventures on Maui on 27 Foot HunterX Monohull

5.0
Superowner
$525/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
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
Sunreef 62 catamaran
Sailing in Maalaea · 12 guests

Sunreef 62 catamaran

5.0
$1,200/hour
Sunset Sails💥$295💥
Sailing in Honolulu · 6 guests

Sunset Sails💥$295💥

5.0
$165/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

Sailing Reviews in Hawaii

  1. 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.

  2. VS

    Valerie

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

    I had family in town visiting (a group of 13) and we decided to book a boat day, which ended up being the highlight of everyone's trip! The captain and crew were fantastic and went above and beyond to make sure we had a good time. We snorkeled with sea turtles, sailed out on the open waters, swam, and relaxed on the netting/ bean bag chairs. Such a fun day. Highly recommend!!!

  3. NT

    Natalie

    Epic 34' Catamaran Sailing in Waikiki

    My group had a fantastic and smooth experience with Captain Polu. Easy to find the boat, very clean and well kept boat, and he had snorkel gear for all of us.

  4. MM

    Mallory

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

    We had the best time on our private sale ! It was perfectly relaxing, beautiful, and fun. They had snorkel equipment and took us out to a beautiful snorkel spot. Wouldn’t have wanted to get out to sea with anyone else !

  5. Claudia

    Claudia

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

    The best day ever with the BEST crew! This was the highlight of our vacation. We will come to Oahu again just to hang with this crew and sail the seas! We even saw whales!

  6. TL

    Tiffany

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

    Captain R responded quickly and communication was very friendly and clear. Thanks for a great day!