Our Fleet

Private Catamaran Sailing Charters

1/2 day, one-day, sunset, dinner, multi-day to multi-week inter-island vacation, and trip options are available.

Hawaii Sailing Adventures is proud and committed to offering you a unique, unusual, adventurous experience on the best and only private pleasure sailing catamarans available in all Hawaiian islands. Sail Maui, Oahu, and the rest of Hawaii by our luxurious and private catamaran charters.

All our boats are individually owned and well maintained, giving you the benefits of pride of ownership. Hawaii Sailing Adventures delivers personal attention, years of experience, and a love of sailing Hawaii's islands and waters. We have local insights, a love of Hawaiian culture, and want to share the beauty of land and sea life above and below.

We are all Hawaii locals, lovers of the deep ocean, owners, captains, and sailors. In addition, we have sailed on these boats all around the Pacific Ocean from the Caribbean, Panama, Mexico, Tahiti, and more.

If you want a truly intimate and adventurous vacation, contact Hawaii Sailing adventures today for more information about private charters.

Explore Our Fleet

  • All
  • Catamarans
  • Sailboats
top view anchored

Sunreef 70

catamaran charters

Sunreef 62

aqua water side view anchored

Isara 50

snorkeling Lanai

Fountaine Pajot Bahia 46

Lagoon 440 Fly Bridge Catamaran Charter

Lagoon 440 Fly Bridge

people on boat and in water sand bar

Fountaine Pajot Helia 44

Catamaran Maui

Excess 12 – 39’

side view Hale Lono

Beneteau Oceanis 50

under sail 1

Beneteau Oceanis 48

saling 3

Nautor Swan 46

under sail, Daimond Head

CSY 44


Beneteau 42

stern view

Beneteau Oceanis 41

side view group 1

Beneteau 393


Beneteau 39

The Sunreef 62 - As seen on NETFLIX

The Sunreef 62 is featured in the Netflix series “The most Amazing Vacation Rentals” “episode titled "Aloha Hawaii” Season 1, Episode 9.

Click here to learn more.

We're proud to offer the "only catamaran sailboats available for private vacation charter in all of the Hawaiian Islands" Just your family and friends

What our customers say...

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Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.