Private Hawaiian Catamaran, Sailing and Yacht Charters

IT'S TIME FOR THE VACATION OF YOUR DREAMS

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

Featured in the Netflix series “The most Amazing Vacation Rentals” Episode 1, Season 9.

Hawaii Sailing Adventures offers private boats, catamaran charters, and sailing trips on our luxury fleet. We provide charter options for Maui, Kaanapali, Kauai, Niihau, Lanai, Molokai, Honolulu, Waikiki, Oahu, Kaneohe Bay, and The Big Island. We can also show you the "unknown" islands of Hawaii. Visit Napali Coast, Kaanapali & Kohala Coast, whale watch, snorkel and more!

Enjoy extraordinary encounters with whales, dolphins, and sea turtles, snorkeling, swim in tropical island waters and have the best sailing experience in your lifetime. Create a memorable adventure for your family and friends with Hawaii Sailing Adventures.

Explore Our Fleet

All
  • All
  • Catamarans
  • Sailboats
  • Yachts
2 charter-blaze-17

Sunreef 62

aqua water side view anchored

Isara 50

Untitled-53

Custom 50

snorkeling Lanai

Fountaine Pajot Bahia 46

stern steps

Fountaine Pajot Belize 43

anchored bow

Excess 12 – 39’

stern view

Beneteau Oceanis 41

side view group 1

Beneteau 393

saling 3

Nautor Swan 46

top

Sunseeker Predator 75

OLYMPUS DIGITAL CAMERA

Beneteau 39

Untitled-10

Beneteau 42

Ready to find out more?

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

Napali Coast, "The Forbidden Island", North Shore Molokai, Kanaapali, Manele Bay

Niihau, Kalalau Valley, lagoon, reefs and beaches, sea cliffs, waterfalls, snorkel, scuba, swim, sunbathe, kayak, paddleboard, surf, windsurf, fish, and dine ashore. Stay in the harbor as a pleasant, charming, quiet, relaxing home base with all the cooking and sleeping amenities, a more creative environment than a hotel or house, and explore on-island activities on a week or two sailing charter. Relax, work the sails, whale watch, extended inter-island trips, short sailing tours, sunset sail, and dinner cruise. Feel what it is like to offshore cruise in the most dramatically beautiful settings in the world. Our crewed sailing and luxury yacht charters and boat tour prices include skipper, food, fuel, gear, other vessel costs, Sail Blue Hawaii, and much more.

What our customers say...

A Dream Wedding in Hawaii

Ask us about our tropical, romantic wedding and honeymoon packages. Then, let us arrange your marriage ceremony aboard your private yacht.

Catamaran and Monohull sailboats to; Maui, Lahaina, Molokai, Lanai, Oahu, Honolulu, Kauai, Niihau, Big Island Hawaii.