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All listings in Hawaii

Incredible sailboat rentals in Hawaii, United States.

Page 2 of 241 listings

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
Waikiki Sunset Boat Charters and Custom Day Tours
Sailing in Honolulu · 8 guests

Waikiki Sunset Boat Charters and Custom Day Tours

5.0
$99person
Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!
Events in Honolulu · 12 guests

Private Luxury 50' Catamaran Snorkelling, Sunset, Sailing, Dolphins, Fireworks!

New
$999hour
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
Best Sunset Cruise 50' Luxury Private Yacht. Book your sunset cruise today!
Sailing in Honolulu · 12 guests

Best Sunset Cruise 50' Luxury Private Yacht. Book your sunset cruise today!

New
Superowner
Best of 2023
$499hour
Sail Kaneohe Bay and Sand Bar, beautiful Catalina 27
Sailing in Kaneohe · 4 guests

Sail Kaneohe Bay and Sand Bar, beautiful Catalina 27

New
$800day
Largest, most luxurious sailing catamaran on the island of Oahu
Events in Honolulu · 12 guests

Largest, most luxurious sailing catamaran on the island of Oahu

New
$1,119-$1,499hour
Fountaine Pajot Helia 44 Cruising Catamaran
Sailing in Honolulu · 6 guests

Fountaine Pajot Helia 44 Cruising Catamaran

New
$1,500hour
*** $99 per person/hr, 5 people minimum booking 3 hr minimum sailing required
Sailing in Honolulu · 12 guests

*** $99 per person/hr, 5 people minimum booking 3 hr minimum sailing required

New
$99person
60 Passenger Private Luxury Searunner 54 Catamaran In Honolulu
Sailing in Honolulu · 60 guests

60 Passenger Private Luxury Searunner 54 Catamaran In Honolulu

New
$1,750hour
***99.00/ person/hr ***COME SAIL THE DREAM ON OUR LUXURY 52 ft SAILING YACHT***
Sailing in Honolulu · 12 guests

***99.00/ person/hr ***COME SAIL THE DREAM ON OUR LUXURY 52 ft SAILING YACHT***

New
$99person
Brand new 2022 Excess 12 - 39' Luxury Catamaran (Oahu only)
Sailing in Honolulu · 10 guests

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

New
$4,500day
Isara 50ft Sailing Catamaran, Ultimate Luxury and Quality
Sailing in Honolulu · 12 guests

Isara 50ft Sailing Catamaran, Ultimate Luxury and Quality

New
$1,200hour
Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii
Sailing in Honolulu · 6 guests

Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii

5.0
$475hour
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
Private Snorkeling and Sailing Charter
Sailing in Wailea-Makena · 49 guests

Private Snorkeling and Sailing Charter

New
$1,100hour

Sailing Reviews in Hawaii

  1. 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

  2. Joanne

    Joanne

    Waikiki Sunset Boat Charters and Custom Day Tours

    Brendan supplied us with an excellent experience on the ocean waters. He took an extra step to grab us up at our hotel so we didn’t have to walk in the sun with all our stuff to the harbor. He provided us with all the necessary equipment we needed to have while in the water, snorkeling gear, floating board etc. It was a really fun day and he made the day easy and enjoyable.

  3. GINA

    GINA

    The SV Praha Luxury Sailing Yacht in Honolulu, Hawaii

    What an amazing experience! In January, we saw and amazing number go dolphins, whales and even a giant sea turtle. The boat is absolutely beautiful. The crew was super attentive and very knowledgable. They provided a ton information and answered all of our questions about the islands. We were lucky and got perfect weather and temp. I've been to Oahu many times and have never seen it from this perspective before. I highly recommend it. Even thought it was smooth sailing, I do recommend Dramamine if you aren't used to being on the water like us city girls. Life's short...get the boat!!

  4. 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.

  5. 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!

  6. JB

    JUAN CARLOS

    Private Sailing Adventure on a Performance Catamaran in Honolulu, Hawaii

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