Private Hawaiian Catamaran, Sailing and Yacht Charters


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.  Snorkel, whale watch and visit Napali Coast, Kaanapali & Kohala Coast, exploring the beautiful "unknown" Hawaii through our one of our luxury boat trips.

Contact us to learn more about booking a private catamaran or boat charter where you'll create a memorable adventure for your family and friends. Enjoy extraordinary encounters with whales, dolphins, and sea turtles, swim and snorkel in tropical island waters and have the best sailing experience in your lifetime!

Explore Our Fleet

  • All
  • Catamarans
  • Sailboats
  • Yachts
top view anchored

Sunreef 70

catamaran charters

Sunreef 62

aqua water side view anchored

Isara 50


Custom 49 catamaran

2 boats

Leopard 47

snorkeling Lanai

Fountaine Pajot Bahia 46

people on boat and in water sand bar

Fountaine Pajot Helia 44

Catamaran Maui

Excess 12 – 39’


42 Catalina MK 11

Top view Waikiki (1)

Traylor 65

under sail 1

Beneteau Oceanis 48

saling 3

Nautor Swan 46


Beneteau 42

stern view

Beneteau Oceanis 41

side view group 1

Beneteau 393


Beneteau 39

top view

Ferretti 69


Chesapeake Bay 36

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.