4 Sunset Sailing Cruises in Maui to Build a Day Around

1.‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114Our pick

Board Sail Maui’s Alihilani at Maalaea Harbor for a two-hour sunset sail in the Auau Channel. You’ll find cold hors d’oeuvres, drinks, open deck space, forward trampolines, and an English-speaking crew. From December through March, keep watch for humpback whales.

“We really enjoyed our sunset cruise, the crew was fun and attentively engaged with the passengers -checking on & asking if people wanted a drink brought out to the deck. As well as being willing totake pictures. It was my most favorite activity in Maui, because it was so relaxed for my hisband & I- we loved sitting on the net and watching the sunset. Not rushed and a highlight of our vacation!”

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2.Sunset Sail from Ma’alaea Harbor

★★★★★★★★★★4.5 · 207 reviews · from $151

Sail aboard the Ocean Spirit catamaran from Ma’alaea Harbor for about two hours. You’ll get island-style music, appetizers, coffee, tea, and non-alcoholic drinks while watching the Pacific sunset. Humpback whales may appear in season. Confirm current alcohol rules before booking.

“Had a delightful sunset cruise recently. The water was calm, sailing was smooth, and the crew was attentive. The drinks were fantastic, and the Hawaiian music set a perfect vibe. While the appetizers were just okay, the overall experience was very enjoyable. No whales spoRead more”

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3.Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.7 · 150 reviews · 2 hours · from $134

Board Teralani’s luxury catamaran directly from Ka'anapali Beach for a two-hour sunset sail. Enjoy premium drinks, Hawaiian beer, wine, Mai Tais, pupus, and 360-degree views of the Pacific and West Maui Mountains. From November through April, you may also spot humpback whales, though this is not a formal whale watch.

“Fabulous and fun crew. Very safe and lovely tour! Mario and Bree were awesome as was the captain!!!”

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4.Ka’anapali Luxury Sunset Dinner Sail

★★★★★★★★★★4.8 · 123 reviews · 2h 30m · from $169

Spend 150 minutes aboard Teralani’s luxury catamaran, loading directly from Ka’anapali Beach for a sunset sail with buffet dinner, premium drinks, and views of the West Maui Mountains. Crew members such as Captain Patrick and Captain Sam add local insight, while seasonal whale sightings can turn dinner into a wildlife show.

“It was absolutely fantastic! The sunset was beautiful. We did not see any whales breach but we got to see some whales. The meal was great Good music and good appetizers”

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