Kai Kanani sailing   Four Winds Sailing  

We recommend the above Sailing Vessels.

Maui Sailing Activities

The following are some of the many things you can do while sailing in Hawaii.

Sunset CruiseMaui Sunset Cruise

Our favorite thing to do is take a cocktail cruise at sunset. You'll enjoy warm ocean breezes while sipping on drinks, indulging in tasty pupus, and watching a perfect Maui sunset while enjoying your time with your friends and family.


IslandInter-Island Exploration

Maui County is perfect for exploration because it's made of multiple islands. You can do day trips to Lanai and Molokai, or you can take an overnight trip to some of the outer-islands (reserve the Island Star for overnight excursions.)


Scuba DivingScuba Diving

Maui and Lanai are both famous for their scuba diving sites. The back-side of Molokini Crater is world-famous for diving as well as Lanai's Cathedrals are famous for their cave diving.



Snorkeling can be done off-shore with the rest of the masses, but it's nice to get away and enjoy off-shore spots like Molokini Crater. This marine sanctuary is protected from swell and usually has high-visibility. You can also go to Turtle Town or to La Perouse Bay.


Snuba DivingSnuba

If you're not completely ready for scuba diving, but you want more than snorkeling can offer you, Snuba is the solution. With Snuba you can dive deep without a tank on your back. Tubes run up to your tank, which floats on the surface and follows you as you explore.


WhalesWhale Watching

Humpback whales are famous for their surface activity. Watching them breach is one of the more exciting natural experiences you're likely to observe. With a whale watch, you can sail beside these huge and graceful animals.



Fun Sailing FactsSailing Activities

Recommended Boats

Four Winds Sailing Charter

Makena Sailing Charter

Fun Sailing Facts

  • Variation = error in a compass caused by the magnetic field of the Earth, which changes around the world.
  • Deviation = error in a compass caused by the large metal parts of the sailing vessel.
  • Leeway = is when a vessel drifts to one side due to the wind strength, which can further complicate sailing direction. Good captains take all of these factors into account when traveling to a particular destination.
  • Weather refers to the side of a boat that is getting the wind. Lee is the side that is calm.
  • Tacking towards the Starboard (right) gives you right-of-way over all vessels to your port side.

    Fun Maui Information

  • Maui County leads the Hawaiian Islands in whale watching because Humpback whales use the Auau Channel between the islands to enjoy winter. They spend their winters here to give birth and mate. Their journey consists of over 3,500 miles from Alaskan waters every year!