Category Maui Sunset Sails & Dinner Cruises

Maui · MAUI SUNSET SAILS & DINNER CRUISES

The 15 Best Sunset Sails & Dinner Cruises on Maui

25 reviewed

The west side faces the sunset, which is why the evening boats leave Kaanapali and Maalaea just before the light turns gold. Ranked below are the best sunset sails and dinner cruises: which serve a full plated dinner versus pupus and drinks, which keep the bar open, what each costs, and which one to save for a special night.

Maui: Original Sunset Cruise with Open Bar from Ka’anapali Beach

Maui: Original Sunset Cruise with Open Bar from Ka’anapali Beach - Open Bar and Heavy Pupus: the value question (and the best way to use it)

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

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

Ka’anapali sunset catamaran with open bar and heavy pupus plus winter whales. Barefoot beach boarding, great crew, ~2 hours.

“This is an easy, pleasant sail along the Maui coast. Nick, James and Em (I hope I remembered their names correctly!) were great hosts and provided a great experience for all onboard. The drinks were plentiful and the food was good. A really great sunset sail.”

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Maui Premium Sunset Dinner Cruise from Ka’anapali Beach

Maui Premium Sunset Dinner Cruise from Ka’anapali Beach - Meeting at Sea Maui and Boarding From the Beach Walk

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

From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver - Dinner on a Maui boat: the real value is a full 3-course meal

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

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

Maui sunset dinner cruise on the Quicksilver catamaran from Ma’alaea Harbor with 3-course local dinner, two drinks, live music, and views of Lanai and Lahaina.

“When I booked the trip, I told them we are going to Kona. They booked our trip on Maui, so when we got to Kona there was no trip for myself and my family. I do appreciate that you did return our money. Thank you for that.”

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Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

Maui Sunset Dinner Cruise - A Hawaiian Hula Experience - Setting sail on the Pride of Maui (and why the boat size matters)

4.Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

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

Maui sunset dinner cruise with open bar, buffet ribs, live hula and slack-key music, plus possible humpback whales near Molokini.

“We arrived there 45 mins prior. Instructions were not clear. We walked towards Pride of Maui, I showed the gentleman greeting customers our bouchers and he said we were on the wrong place and instruction us to walk to Calypso which was on the other side of the pier. When we got to Calypso, they told us Pride of Mayi is on the other side. I called Viator to confirm which boat it is and I was put on hold for a long time. I was still on hold when we reached Pride of Maui and was agitated already when I spoke to the lady greeting customers. She said we…”

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

Maui Ma'alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise - Boarding the Calypso: tableside service, Hawaiian music, and the onboard bar

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

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

Ma'alaea Harbor sunset dinner cruise on the Calypso catamaran with prime rib or fish, included drinks, music, and whale chances.

“Great food we saw some whales beautiful sunset a wonderful time we had a great time! we also took some great pictures of whales which we weren’t really thinking we were gonna be able to do”

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Maui Premium Sunset Dinner Cruise & Whale Watch

Maui Premium Sunset Dinner Cruise & Whale Watch - 4-course dinner and drinks: what comes with your ticket

6.Maui Premium Sunset Dinner Cruise & Whale Watch

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

Maalaea sunset dinner cruise with live naturalist whale watch, 4-course meal and drinks, plus Pacific views of Lana‘i and Moloka‘i.

“What an amazing experience! We saw so many whales, both adult and babies. March is a great time to go whale watching, especially in Maui. When we come here again, this will be one of the first tours I’ll book!”

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Maui Premium Dinner Cruise: Four Course Dining Experience

Maui Premium Dinner Cruise: Four Course Dining Experience - Timing, check-in, and what the 2.5 hours actually feel like

From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - The Alihilani Catamaran: Deck Space and Comfort That Actually Help

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

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

2-hour Alihilani sunset sail from Ma’alaea Harbor with ice-cold drinks, cold hors d’oeuvres, and a real shot at dolphins and whales.

“Despite choppy waters, the trip was lots of fun. Crew was awesome. Visitors are needed as activity wasn’t very busy as the area is still reeling from the Lahaina fire of August 2023. Maui visitors are warmly welcomed.”

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South Maui: Sunset Prime Rib or Island Fish Dinner Cruise

South Maui: Sunset Prime Rib or Island Fish Dinner Cruise - The sunset route: Kahalawai Mountains, Lanai, Molokini, and more

9.South Maui: Sunset Prime Rib or Island Fish Dinner Cruise

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

2-hour South Maui sunset dinner cruise from Ma‘alaea Harbor with prime rib or mahi-mahi, live music, whales, and sea turtles.

“Our 25th Anniversary Couldn’t Be More Memorable !!! The Crew Was Great - The Captain Outstanding AND THE SUNSET WAS REMARKABLE !!! I’d Suggest This For ANYONE For ANY Occasion !!! FANTABULUOS VOYAGE !!!”

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Haleakala Maui Sunset Twilight Tour with Dinner

Haleakala Maui Sunset Twilight Tour with Dinner - Haleakalā Visitor Center at 7,000 Feet: Where the Weather Sets the Tone

10.Haleakala Maui Sunset Twilight Tour with Dinner

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

Sunset at Haleakalā by coach from Lahaina, with crater views, stars, and Kula Bistro to-go dinner. Small group, weather permitting.

“Our guide Mitch was very friendly and informative. The sunset was amazing! We highly recommend this tour! We could have driven ourselves, but we were glad we did not have to navigate the descent after dark.”

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From Ma’alaea: Sunset Dinner Cruise Aboard the Quicksilver

From Ma'alaea: Sunset Dinner Cruise Aboard the Quicksilver - First stop: Boss Frog’s parking and the easiest way to start

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

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

Two hours on the Quicksilver catamaran with a Maui sunset, live island music, and a table-side 3-course meal plus two included drinks.

“Amazing experience! The crew was wonderful and the captain did a spectacular job narrating our cruise. He knew SO much about the area. Live music was a major bonus-can’t get that anywhere else. Food was delicious. This was the highlight of our trip to Hawaii!!”

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Sunset Sail from Ma’alaea Harbor

Sunset Sail from Ma'alaea Harbor - The Ocean Spirit catamaran ride: comfort, group size, and “real” sailing

12.Sunset Sail from Ma’alaea Harbor

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

A 2-hour Maui sunset sail from Ma’alaea Harbor on the Ocean Spirit catamaran with pupus, unlimited non-alcoholic drinks, and possible whales.

“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 spotted due to time of year, and sunset was blocked by clouds, but plenty of room on the boat and a delightful crew. Would recommend for a relaxing evening on the water. Attended with 2 other couples. Oly recommendations would be for the crew to tell us a bit about the area or sights -- not too heavy but a little detail would have been nice.”

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Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar - The Teralani Catamaran Experience: Comfortable, Stable, Photo-Friendly

Maui: Ka’anapali Luxury Sunset Dinner Sail

Maui: Ka'anapali Luxury Sunset Dinner Sail - 150 Minutes on the Water: Timing, Views, and That Sunset Shift

14.Ka’anapali Luxury Sunset Dinner Sail

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

A 150-minute Ka’anapali sunset sail on a luxury catamaran with direct beach loading, unlimited drinks, and a Hawaiian-inspired buffet.

“Fabulous crew and great dinner and cocktails!! The perfect boat for a large group with plenty of room to relax and stretch out. Tanner, Freddie, Ian and Sammie were knowledgeable and a lot of fun!!”

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Maui: Coast of Ka’anapali Beach Sunset Dinner Sail

Maui: Coast of Ka'anapali Beach Sunset Dinner Sail - What You’ll See: Maui Coastline Views and the Molokai/Lanai Promise

15.Coast of Ka’anapali Beach Sunset Dinner Sail

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

Two-hour Ka'anapali sunset dinner sail with a buffet, open bar, pupus, and possible whale sightings with views of Molokai and Lanai.

“Don't go for the dinner, go for the views from the water. The meal is really basic as should probably be expected on a two-hour boat ride. If you like to be out on the water and take in island views, you should go.”

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