Choose a sailing charter

Why Sail Oahu?

We offer the finest in luxury performance sailing on the largest, most elegant sailing yacht in the fleet. Our Captain and crew are here to see to your every need while providing the highest level of comfort possible aboard a yacht of this caliber.

We will present you with the finest selection of wines and beverages, as our chef prepares an exquisite feast, customized for you. Whether you are a first-time sailor or a seasoned “Shellback,” relax in comfort and pleasure as the Hawaiian trade winds blow us favorably past Diamond Head.

Customize Your Sail!

Have a special day in mind? Tell us about it. We can provide a no-obligation quote tailored to your perfect day in paradise. We also guarantee our quote for 60 days to give you plenty of time to decide.

Set Sail On Your Adventure

We ensure that your day in our blue paradise is spent the way you always dreamed it could be. Experience Hawaii and the Pacific Ocean aboard your private yacht.

All of our charter guests rate us 5 stars on TripAdvisor

Snorkel Cruise on a 70’ sailboat!

Can't say enough good things about Alan and his crew!! So kind. So knowledgeable of the island. We swam up close with turtles and had a freshly made lunch served. We felt like celebrities. Highly recommend!!

– Kay H., TripAdvisor
Best "After Christmas" Sail Ever!!

What an awesome afternoon with Sail Oahu! Captain Alan, First Mate Wanda, and crew are first class in every way. We had a beautiful day with stunning views of Waikiki and Diamond Head - with wine, beer, and a delicious lunch to top off the trip. The sailboat was impeccable, impressive and well appointed. We felt well cared for and very welcome. We are looking forward to our next visit to the island and another afternoon with Sail Oahu.

– mzak0506, TripAdvisor
Best Birthday Ever!!

Sail Oahu was Soo Much Fun!!! I had the best day celebrating my birthday!! Captain Alan and First Mate Wanda will make your Trip so enjoyable! They are amazing hosts! And their boat is so classy! I felt like a princess! And the views of Diamond Head were breathtaking!! I will definitely Sail with them again!!

– AnnieSelby, TripAdvisor
Sail Away, Sail Away, Sail Away

Sail Oahu was one of the most exciting, tranquil, humbling experiences of my life. Capt. Alan, his mate Wanda, and the entire crew were so welcoming & warm. They were particularly great with my nieces and nephews (ages 3-10) as well! They always put safety and comfort first! The sailboat itself is beautiful and lavish. The views of the Island from the open water were breathtaking. I will definitely Sail Oahu every trip I make to the island.

– leslie00seven, TripAdvisor
What a fantastic experience!

A fantastic day out with my friends with breathtaking views, lovely food, and a stunning boat. The crew were amazing people with such interesting stories, they really made us feel like a big happy family. I recommend this for all families, friend groups, young and old. A day I will never forget! Thank you Sail Oahu and hope to see you soon.

– Willers I., TripAdvisor