Kai Kanani sailing   Four Winds Sailing  

We recommend the above Sailing Vessels.

Maui Sailing Destinations

Lanai IslandLanai Island

Lanai is world famous for its scuba diving. Above water, it has many other hidden gems including long beautiful empty beaches. Lanai is a great place to explore for the day.


Molokini CraterLa Perouse

Your best chance of seeing spinner dolphins in Maui would be at La Perouse Bay. This bay is in South Maui and has great snorkeling along the rocky volcanic coastline.


Molokai IslandMolokai Island

Quite desolate, Molokai is home to some of the highest sea cliffs in the world. Many waterfalls drape over these cliffs, falling into the ocean making for an unforgettable experience.


Molokini CraterMolokini Crater

Snorkeling inside of the crater, and scuba diving on the back-side wall are both world famous. The back-side drops to around 300 feet in depth. The inside of Molokini Crater has a gradual slope, which is protected from swell and weather.


Turtle TownTurtle Town

Turtle town is a mysterious place. It refers to the area where turtles are most often found. This area is constantly changing, which makes a captain's insight quite valuable.


Napali CoastOuter Islands

Take an overnight trip sailing to Oahu, Kauai, or the Big Island. Nothing beats traveling by sail and landing in yet another exotic port.


South MauiSouth & West Maui

This is the best area to see whales in Maui, Hawaii. Humpback whales travel thousands of miles each year to spend their winters in the channel between Maui, Kahoolawe, Lanai, and Molokai.



Fun Sailing FactsIsland Navigation

  • Kahoolawe Island Learn how important the island of Kahoolawe has been to navigation and learning to the ancient Hawaiians and Polynesians.

Recommended Boats

Four Winds Sailing Charter

Makena Sailing Charter

Fun Sailing Facts

  • While sailing, the relative wind generated by the movement is called Apparent Wind. 
  • A Burgee is a small type of wind vane that is attached to the top of the mast in order to best gauge wind direction.
  • Running = Running rigging will control the sail movement.
  • Sheets = Ropes used to adjust the sail for direction.
  • Halyards = Ropes used to hoist and lower the sails.
  • Standing Rigging = Supports the mast.

    Fun Maui Information

  • Many believe that the Hawaiian Islands were formed from underwater volcanoes pouring out of hot spots in the pacific tectonic plate. According to Hawaiian legend, the demi-god Maui pulled the Hawaiian Islands from the sea with his fishing hook.