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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 2 of 234 listings

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
Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht
Sailing in Honolulu · 6 guests

Scandinavian Quality Sailboat | Nautor Swan Gecco 39 Yacht

New
$1,800/day
Come and Sail on this Beautiful 50' Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 6 guests

Come and Sail on this Beautiful 50' Catamaran in Honolulu, Hawaii

New
$500/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
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
Snoozed - Active 08 Oct 2025
Private South Shore Day Sail
Sailing in Honolulu · 49 guests

Private South Shore Day Sail

New
Snoozed - Active 30 Sep 2025
Honolulu Private Morning Ceremony Sail Catamaran Charter Oahu, USA
Sailing in Honolulu · 49 guests

Honolulu Private Morning Ceremony Sail Catamaran Charter Oahu, USA

New
Snoozed - Active 30 Sep 2025
Honolulu Private Sunset Sail
Sailing in Honolulu · 49 guests

Honolulu Private Sunset Sail

New
Snoozed - Active 30 Sep 2025
Honolulu Private Swim & Sail
Tours in Honolulu · 36 guests

Honolulu Private Swim & Sail

New
Snoozed - Active 30 Sep 2025

Sailing Reviews in Hawaii

  1. KV

    Kimberly

    Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii

    So much fun! Jason is very knowledgeable boating and offers some great history. Boat was very comfortable and equipped with items for a great day on the water. Got to see some whales as well. Deckhand was awesome too! Would definitely recommend using for any charter but for sure, I’ll use him again! Thanks Jason & Kevin.

  2. JT

    Jonathan

    46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii

    The team did a great job of communicating before the trip and carried that great service all the way through a fabulous experience on the water. This outing and snorkeling session with the turtles and plenty of fish was the highlight of our time in Ko’ Olina. We will be repeat customers because of how easy it all came together. Customer service can be so easy when done right, and your team delivered!!! Thanks. — Todd family

  3. Simon

    Simon

    46ft Luxe Private Sailing Catamaran Charter in Ko Olina, Hawaii

    We had an unforgettable day on the great boat. Everything was perfect: the team, the food, the dolphins and turtles we saw and the snorkeling together. A perfect day!

  4. JB

    JUAN CARLOS

    Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii

    Excellent Catamaran experience, top service, and great food! Highly recommended!