11 Sunset Cruises in Maui to Build a Day Around

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

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

Sail from Ka’anapali Beach for about two hours with unlimited cocktails, non-alcoholic drinks, and hearty pupus. The barefoot catamaran carries up to 48 people and may spot whales from December 15 through April 15. Expect live music on some Tuesdays and Thursdays, beach boarding, and possible spray on the way out.

“It was a great ride with amazing views of the sunset, but also WHALES! We saw more whales on this trip than we did on our whale watching tour. The people were great and the drinks were delicious. It was a relaxing night. Would schedule again.”

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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 out 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 live music on Wednesdays and Saturdays. From December 15 through April 15, the crew also watches for humpback whales. Expect wet feet when boarding from the sand.

“Beautiful sunset cruise. We ate and drank well, and saw many whales. A few breached. The boat’s driver needs to work on his whale approach instincts, and I wish he would cut the engines when close to them.”

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

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

Board the Quicksilver catamaran at Ma’alaea Harbor for a two-hour sunset cruise with table-side service, island-style music, and a three-course dinner. Choose prime rib, mahi-mahi, ribs, chicken, or vegetarian pasta. Two alcoholic drinks are included, and winter sailings may bring humpback whale sightings.

“Great experience as to cruise, music, food and photographer. Only suggestion is send out the email about traffic, parking, etc earlier in the day. Received it at 2pm for a 5pm cruise.”

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4.Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

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

Cruise Maui’s coast aboard the spacious Pride of Maui catamaran for a two-hour sunset outing near Molokini. You’ll get a buffet of ribs, shoyu chicken, vegetables, and coconut sweet potatoes, plus an open bar with microbrewed beer, wine, cocktails, and mocktails. Live Hawaiian slack key music and hula add a real island touch, and winter sailings may include humpback whales.

“This is a great late afternoon excursion. We'll worth the price and during whale watching season added immense pleasure to the trip.”

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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 cruise with table-side dinner service, island-style music, and a full bar. Choose prime rib, fresh fish, ribs, smoked chicken, or pasta. The crew may also point out whales during winter sailings, and photographer Marley is often aboard for optional pictures.

“Celebrated my sister's birthday in style! The service was exceptional. Very warm and welcoming staff on board. We had the fish dinner which was very delicious. Loved the sunset made dinner extra special.”

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6.Maui Premium Sunset Dinner Cruise & Whale Watch

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

Set out from Maalaea Harbor on a three-hour Pacific Whale Foundation cruise with a four-course dinner, alcoholic drinks, and live naturalist commentary. Watch for migrating humpbacks, listen for whale song, and take in sunset views toward Lana‘i and Moloka‘i. Captains and naturalists such as Andrew, Stevie, Ash, and Chris have helped make past trips memorable.

“The crew was awesome. Our captain was just as excited as we were to see the whales. Because we had the most sightings and preachings they had ever seen and us as well.”

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7.From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

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

Sail Maui’s ‘Alihilani takes you from Ma’alaea Harbor into the Au‘Au Channel for a two-hour sunset sail. Relax on the forward trampolines or under the cabin with included drinks and cold hors d’oeuvres. The English-speaking crew, often including staff such as James, Kevin, Jess, Nicholas, or Patrick, keeps service friendly and attentive.

“10/10 would do again! Great crew - great time! Worth it! Spent half day in Lanai then came and did this, THEN went to Lahaina pizza company. Full day and was awesome!”

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8.Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!

★★★★★★★★★★5.0 · 264 reviews · 1 hour (approx.) · from $420

Take a private one-hour flight for up to three people from Kahului over Maui’s beaches, resorts, central valley, Molokini Crater, and Kaho'olawe. Your pilot provides live commentary through a headset, then you celebrate with a glass of champagne after landing. Steve and Eric are among the pilots praised for friendly, clear island insight.

“We enjoyed a romantic ride on the most beautiful night! Our pilot was very knowledgeable about the island and was able to answer our many questions. I would highly recommend!”

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9.Sunset Prime Rib or Island Fish Dinner Cruise

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

From Ma’alaea Harbor, you’ll spend two hours aboard Calypso Molokini Charters’ roomy triple-decker catamaran, with dinner, live music, two alcoholic drinks, and sunset views of Maui, Lanai, Kaho’olawe, and Molokini. Chef Keoni’s menu includes prime rib, Mahi-Mahi, chicken, ribs, or vegetarian pasta. Whale sightings are possible from December through April.

“Great trip. Jill and Bree were knowledgeable and helpful. They found the whales and I would definitely go again.”

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10.Haleakala Maui Sunset Twilight Tour with Dinner

★★★★★★★★★★4.5 · 240 reviews · 7 hours (approx.) · from $256

Ride an air-conditioned coach from Lahaina to Haleakala’s 9,740-foot summit for sunset, crater views, and stars. The tour includes park admission, narration, a Kula stop, and a to-go dinner from Kula Bistro. Guides such as Mitchell, Dino, Randall, and Don have been praised for safe driving and local stories, but pickup coordination can be uneven.

“We had a great experience with Mitchell, who was very friendly and informative throughout the entire drive. The sunset was stunning and he took us directly to a prime viewing area. We are so glad we didn’t drive ourselves, as some parts of the roads don’t have railings and there are sometimes random cows on the road. Don drove us back to our hotel and was just as friendly and kind! Highly recommend”

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

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

Board the Quicksilver at Maalaea Harbor for a two-hour sunset cruise with table-side service, a three-course dinner, two alcoholic drinks, and live island-style music on most nights. Choose from prime rib, island fish, ribs, chicken, or vegetarian pasta while watching Maui’s coast, neighboring islands, dolphins, or seasonal whales from the cabin or upper deck.

“Great crew! clean ship! comfortable seats! Great food! beautiful sunset! We weren't sure it would be worth it,v considering there are so many great restaurants to eat at right in the water... but it was definitely fantastic! you get to just see so much more from the ocean! love seeing the islands from the water and search for paces we have been. The sun setting with unobstructed views is gorgeous. God is the ultimate artist!”

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