Private Catamaran Sailing Charter Trips in Maui

Perfect for family trips, weddings, honeymoons and vacations.

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

As Hawaii's second largest island, Maui boasts white sand, crystal clear water, black sand beaches, waterfalls & mountains. With Hawaii Sailing Adventures, you can sail Maui by booking a private sailboat charter and luxuriously exploring the white, black, and red beaches or many activities, including sailing, surfing, paddleboard, kayaking, snorkeling, scuba, biking, windsurfing, swimming, shopping, eating. Our boat routes are perfect for family trips, friends, weddings, honeymoons, birthdays, anniversaries, and vacations.

We offer the only private vacation sailing catamarans and the most extensive fleet of monohulls available on and inter-island to Maui from the neighboring island for just your family and friends.

Contact us today to talk about booking your Hawaiian vacation!

Explore Our Maui Fleet

top view anchored

Sunreef 70

catamaran charters

Sunreef 62

aqua water side view anchored

Isara 50

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

under sail 1

Beneteau Oceanis 48

saling 3

Nautor Swan 46

top view

Ferretti 69


Chesapeake Bay 36

Visit one of the luxury spa resorts on Kaanapali beach.

  • See “tons” of frolicking Humpback whales.
  • Snorkel, sunbathe, fish, surf, sail, swim, relax.
  • Maui, Lanai and Molokai, short sails between islands.
  • Fishing is great and we know the most amazing snorkel spots.
  • Lahaina is a historic whaling town, beautiful art galleries, wonderful upscale restaurants.

Sailing Maui and Oahu is a weather friendly option for Winter.

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

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