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.
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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
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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