Maui Sunset Sails and Catamarans

Maui Sailing

Maui sailing is all about ocean breezes, sunset light and views of the neighboring islands. Depart from Kaanapali or Maalaea for cocktail cruises, stargazing sails and seasonal whale watching.

About this experience

Ease Into the Evening on a Maui Sail

A sailing tour is a nice way to let the day taper off without adding another long drive or packed itinerary. Once you leave the shoreline behind, Maui starts to look different from the water, with the West Maui Mountains, nearby islands, and the changing evening sky all becoming part of the view.

Current options include Sea Maui sunset cocktail cruises from Kaanapali Beach, Hawaii Nautical’s small-group luxury sunset cruise from Maalaea, Pacific Whale Foundation sunset sails, a sunset and celestial stargazing cruise, Ocean Spirit from West Maui, and Malolo’s sunset cocktail cruise from Maalaea.

The feel of the evening depends a lot on the boat and departure point. Kaanapali keeps you close to West Maui, while Maalaea opens up views toward more of the central and south side. Some cruises are built around cocktails and appetizers, while others add live music, a quieter luxury feel, or stargazing after sunset.

If you are visiting during whale season, you may also spot humpbacks along the way. Sightings are never guaranteed, but they can turn an already beautiful evening into something you will remember long after the sail is over.

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