Top Sunset Sailing Cruises Near Wailea

Top Sunset Sailing Cruises Near Wailea

Picture of Grace Towle

Grace Towle

Living on Oahu, Grace Towle knows all the best places where locals go.

Set sail in the beautiful waters of Maui with one of the best sailing cruises in Wailea. You can either cruise at sunset or, if you are here during the winter months, you can search for humpback whales on a morning cruise. The cruises depart from either Maalaea Harbor (about a 22-minute drive from Wailea Beach) or Maluaka Beach, and each lasts around 3 hours. Make sure to book ahead, as cruises are very popular.

Photo Credit: Kai Kanani Catamaran Tours

Kai Kanani Exclusive Catamaran Tours

Check-in: Maluaka Beach
Price: Starting at $135

Beach-loading off of Maluaka Beach in Makena, South Maui, Kai Kanani offers many appealing tours. Go for an early morning snorkel and have Molokini all to yourself. Or sleep in and enjoy the deep blue ocean while the sun is high. And if sunset is your mood-maker, come aboard for appetizers and an open bar and leave the crowds behind.

Pride of Maui Sunset Luau Dinner Cruise - Open Bar & Polynesian Show

Check-in: Maalaea Harbor
Price: Starting at $175
Hop aboard the Pride of Maui. This cruise offers a premium Hawaiian dinner, an open bar, live music and a Polynesian dance show. This cruise is ideal for families, groups and couples.

Trilogy Maui Cocktail Sunset Sail - Premium Open Bar & Gourmet Tapas

Check-in: Maalaea Harbor
Price: Starting at $111

Take in spectacular sunset views on one of the best cocktail sunset sails on Maui, and relax aboard a luxurious sailing catamaran and enjoy a premium open bar and gourmet tapas.

Alii Nui Royal Feast - Maui Sunset Dinner Cruise with Open Bar

Check-in: Maalaea Harbor
Price: Starting at $229

Experience a premium dining experience aboard Alii Nui, the finest sunset dinner cruise on Maui. This adult-only sail is limited to 40 passengers for comfort. Enjoy a premium dinner menu selection and full open bar.

Calypso Maui Sunset Dinner Cruise & Island Music

Check-in: Maalaea Harbor
Price: Starting at $144

Enjoy a 2-hour Maui sunset dinner cruise aboard Calypso, a comfortable, triple-deck catamaran featuring 3-course dinner, local island music, table service and two free drinks.

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