The 15 Best Sunset Cruises on Maui

1.Original Sunset Cruise with Open Bar from Ka’anapali Beach

★★★★★★★★★★5.0 · 1,422 reviews · 2 hours (approx.) · from $127Our pick

Board Sea Maui’s barefoot catamaran at Ka’anapali Beach for a two-hour sunset sail with unlimited cocktails, soft drinks, and hearty pupus. The crew, including names such as Tommy, Travis, Jenni, and Mario, keeps service lively. Expect island views, possible whales or dolphins, and wet feet during beach loading.

“Best experience solo traveling in Maui! Thank you Sea Maui crew for an unforgettable night! The crew kept the drinks flowing and the vibes going. Shout out to Tommy for being especially attentive to all the guests 😊 Definitely coming back!”

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2.Maui Premium Sunset Dinner Cruise from Ka’anapali Beach

★★★★★★★★★★5.0 · 903 reviews · 2 hours 30 minutes (approx.) · from $166

Set sail from Ka’anapali Beach aboard Sea Maui’s 65-foot catamaran for a 2.5-hour sunset cruise with a chef-prepared buffet, full open bar, indoor and outdoor seating, and seasonal whale watching. Crew members such as Kay, Tim, and Kyle have earned praise for friendly service, while boarding from the sand means you should expect wet feet.

“Best crew and whale watching experiences. Highly recommend. The crew was friendly. Reverting air this evening was perfect.”

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3.From Ma’alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

★★★★★★★★★★4.5 · 826 reviews · 2 hours (approx.) · from $139

Set sail from Ma'alaea Harbor at 5 p.m. aboard the double-decker Quicksilver catamaran for a two-hour sunset dinner cruise. Enjoy a three-course meal, two alcoholic drinks, live island-style music, and views toward Lahaina and Lanai. Winter sailings may include humpback whale sightings.

“We had a great time on the dinner cruise! The staff and food was great! The only issue I have was that there wasn’t much cruise time! We stopped in a cove and parked. Parking at the event was a little confusing, we barely made it.”

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4.Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

★★★★★★★★★★4.5 · 703 reviews · 2 hours (approx.) · from $158

Board the spacious Pride of Maui at 5:00 pm for a two-hour coastal sunset cruise near Molokini. Enjoy ribs, shoyu chicken, roasted vegetables, coconut sweet potatoes, dessert, an open bar, live Hawaiian slack key music from Kekoa, and a hula performance. Humpback whales may appear from January through February.

“All was very nice except the directions to the pier were missed by us so we needed to call Viator in New York for help and that took so long we ended up asking at another pier where to go :(”

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5.Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise

★★★★★★★★★★4.5 · 533 reviews · 2 hours (approx.) · from $149

Board the three-story Calypso at Maalaea Harbor for a two-hour sunset dinner cruise with table-side service, island music, two included alcoholic drinks, and choices such as prime rib, mahi mahi, ribs, chicken, or pasta. Seasonal whale sightings can add a memorable bonus.

“Very pleasant evening. Nice service. Pretty good food. Drinks were good. The ride out was very nice with lots of whale sightings and a beautiful sunset.”

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6.Maui Premium Sunset Dinner Cruise & Whale Watch

★★★★★★★★★★4.5 · 504 reviews · 3 hours (approx.) · from $189

Board at Maalaea Harbor for a roughly three-hour sunset cruise with a four-course dinner, alcoholic drinks, and live naturalist commentary. You may see humpback whales, dolphins, and hear whale song through a hydrophone. Captains Andrew and Chris, plus naturalists Ash and Stevie, have earned special praise.

“We got the opportunity to see three whales and it was beautiful! Learned about whales and a little extra about sharks from Ash. We had a great time. Thank you to the crew as they were amazing and kept us well informed and safe. We had never done a whale watching tour and we are so happy we did. My wife and I talked about our experience and we were just mesmerized by the beautiful creatures in the ocean that sometimes we forget about. The beauty Mother Nature has to offer is just priceless! Something’s are just meant to me memories in ur mind because there is no phone or…”

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7.Maui Premium Dinner Cruise: Four Course Dining Experience

★★★★★★★★★★4.5 · 373 reviews · 2 hours 30 minutes (approx.) · from $170

Cruise Maui’s coast for about 2.5 hours while enjoying a four-course dinner, drinks, music, and sunset views of Molokini, Kaho‘olawe, Lanai, and the Pacific. Choose chicken, short rib, shrimp, or Portobello mushroom. Check in 45 minutes early at Maalaea Harbor.

“This dinner cruise is absolutely beautiful and fun. The staff were so cool and the food was delicious. We would highly recommend this to anyone wanting a great night out.”

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8.‘Alihilani Sunset Sail Catamaran Tour

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

Sail Maui’s Alihilani carries you through the Auau Channel from Maalaea Harbor for a two-hour sunset sail. Expect open-deck seating, trampoline nets, drinks, cold hors d’oeuvres, English-speaking crew, and possible dolphins or humpback whales from December through March.

“Absolutely amazing experience! Jamie, Nicholas, and Steven were a fantastic crew, and we would recommend this to anyone coming to Maui!”

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9.Sunset Prime Rib or Island Fish Dinner Cruise

★★★★★★★★★★4.7 · 242 reviews · 2 hours · from $149

Board Calypso Molokini Charters at Ma’alaea Harbor for a two-hour sunset dinner cruise. Chef Keoni serves prime rib, mahi-mahi, chicken, ribs, or vegetarian pasta, while live music, two drinks, whale watching, and views of Lanai and Molokini fill the evening.

“There were so many whales, beautiful music, and delicious food. What a fantastic night!”

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10.Sunset Dinner Cruise Aboard the Quicksilver

★★★★★★★★★★4.5 · 218 reviews · 2 hours · from $139

Spend two hours aboard Quicksilver, a spacious double-deck catamaran sailing from Maalaea Bay. Enjoy a three-course dinner, two alcoholic drinks, island-style music, and sunset views of Maui and nearby islands. Seating may be first come, first served, so arrive early if you want a preferred spot.

“It was an experience of a lifetime! A pod of dolphins on the starboard side and the sunset on the port side, couldn’t decide which way to look. Excellent time for our 25th anniversary!”

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11.Sunset Sail from Ma’alaea Harbor

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

Join Pacific Whale Foundation’s two-hour Ocean Spirit sunset sail from Ma’alaea Harbor. You’ll watch the Pacific turn gold, enjoy island-style music, appetizers, coffee, tea, and soft drinks, and may spot humpback whales in season. Alcohol service has changed, so confirm the current policy before booking.

“We really enjoyed our sunset sail. Our all female crew were fun and hard working (I had no idea of the physical exertion required in hoisting the sail). The food was really good and my beer was cold. But the real attraction was nature itself. Being in the ocean watching the sunset was simply amazing.”

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

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

Board the Teralani catamaran from Ka'anapali Beach for a two-hour sunset sail with ocean views from every table, premium drinks, and pupus including coconut shrimp and teriyaki meatballs. Crew members such as Captain Ian, Anna, and Patrick have earned praise for warm service, while whales may appear from November through April.

“Such an incredibly fun time! Great food and drinks, awesome music, beautiful views, and very welcoming and friendly crew. Thank you so much for a fantastic evening!”

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13.Ka’anapali Luxury Sunset Dinner Sail

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

Board Teralani Sailing Adventures directly from Ka'anapali Beach for a 150-minute sunset sail. You get ocean views from every seat, an open bar, and a buffet of Hawaiian-inspired dishes. Captains such as Patrick and Sam keep watch for whales, while the crew handles drinks, dinner, and beach boarding.

“Incredible experience! One of the highlights of our Maui trip! The crew was very friendly and professional. It was a beautiful night with a gorgeous sunset and the food was very tasty! Not mentioning the variety of cocktails! My husband and I truly enjoyed ourselves as it was very relaxing and enjoyable. Captain Patrick and the crew including Sammy and Miles were amazing. Max took beautiful pictures on board. We highly recommend this activity!!!”

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14.Coast of Ka’anapali Beach Sunset Dinner Sail

★★★★★★★★★★5.0 · 121 reviews · 2 hours (approx.) · from $158

Board Gemini directly from Ka'anapali Beach for a barefoot two-hour sunset sail. Expect a beach launch through shallow surf, views of Maui, Molokai, and Lanai, a buffet dinner, open bar, music, and a crew such as Captain Andrew, Kayla, or Drew, depending on the sailing.

“It was wonderful!! I really felt like I was on vacation. Russell, Arielle and Captain Brad were the best! So fun and nice and helpful. I didnt have high expectations for the food but I was wrong , it was excellent! I highly recommend Gemini. A note to Russell, thanks for helping my hubby when he stumbled getting off the boat. You saved him from going down!!”

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15.‘Alihilani Sunset Sail from Ma’alaea Harbor

★★★★★★★★★★5.0 · 74 reviews · from $112Best value

Board Sail Maui’s 65-foot Alihilani catamaran at Maalaea Harbor for a two-hour sunset sail. You can spread out on the forward trampolines, sit under 575 square feet of covered space, enjoy appetizers and drinks, and watch for humpback whales from December through May.

“So much fun, food and drinks were great. Amazing crew. The humpback whales were putting on an incredible show.”

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