15 Dinner Cruises in Hawaiʻi for a Free Day

1.Big Island Historical Dinner Cruise to Kealakekua Bay

★★★★★★★★★★4.5 · 1,279 reviews · 3 hours (approx.) · from $189Our pick

Sail 24 miles round trip from Kailua Pier to Kealakekua Bay aboard a catamaran with a local historian, live Hawaiian music, sunset views, and dinner. Captain Erika and the crew are known for warm service, while the narrator points out coastline landmarks hidden from land. Vegetarian, vegan, and gluten-free meals require 48 hours’ notice.

“Food was good, crew were amazing and attentive with bringing drinks and offering to take photos. We spotted whales and two manta ray which was an added bonus. There was live music, but it was a hodge podge blend of music that didn’t fit well together and didn’t match the vibe of the boat. A soundtrack would’ve been more enjoyable. It was very overcast and cloudy so we didn’t really witness the sunset at all, but still had a lovely time and enjoyed the ride tremendously. My tip is to not cancel your trip based on weather, as it was still very enjoyable.”

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2.Honolulu: Three Star Deluxe Sunset Dinner Cruise and Show

★★★★★★★★★★4.5 · 1,204 reviews · 2 hours (approx.) · from $193

Sail from Honolulu on the Star of Honolulu for a sunset over Diamond Head, a five-course dinner with lobster or steak, live Hawaiian and jazz music, and a cultural show. You can board independently at Aloha Tower or add hotel pickup from select locations. Friday sailings run longer and may include fireworks.

“Great service and food. Highly enjoyed the entertainment and singers. Fireworks were beautiful. Thank you David. Highly recommend.”

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3.Sunset Dinner Cruise in Honolulu, Hawaii

★★★★★★★★★★4.0 · 1,023 reviews · 2 hours (approx.)

Spend about two hours offshore with views of Waikiki, Diamond Head, and the Pacific sunset. Prince Kuhio Tours serves a freshly prepared dinner of salad, short ribs or mahi-mahi, dessert, and soft drinks. Upper-deck seating depends on capacity. Alcohol is not sold, but you can bring your own for the onboard mixologist.

“It was terrible. They canceled our reservation that we made a month in advance to go to a sunset dinner and they canceled it like three hours before we could’ve chosen so many other things and now you have the nerve to send me a review. It was terrible, terrible terrible with the T the worst ever you should take them off of buy Tours do not sell this to anybody else”

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

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

Sea Maui’s 2.5-hour cruise leaves Ka’anapali Beach aboard a 65-foot catamaran for sunset views, a chef-prepared buffet, and a full open bar. From December 15 to April 15, the crew also searches for humpback whales. You can sit indoors or outside, with live music on Wednesdays and Saturdays. Boarding from the sand means your feet may get wet.

“Great crew good food I would recommend this tour.Check in was easy the crew was very helpful with loading as we entered on the beach”

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

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

Board the Quicksilver at Ma’alaea Harbor for a two-hour sunset cruise toward views of Lanai and Lahaina. You’ll receive table-side service, a three-course dinner, two alcoholic drinks, unlimited soft drinks, and island-style music. Winter departures may include humpback sightings. Arrive 30 minutes early at Boss Frog’s, and request dietary needs when booking.

“The water was way too rough to be out. They canceled the cruise then un canceled it. It was so windy and rough we all got sick. We never get sea sick”

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6.Maui Sunset Dinner Cruise – A Hawaiian Hula Experience

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

Board the Pride of Maui at Maalaea Harbor for a two-hour sunset cruise near Molokini. Enjoy ribs, shoyu chicken, roasted vegetables, dessert, and an open bar with microbrewed beer and blended drinks. Hawaiian musician Kekoa and a hula dancer provide live entertainment, while winter sailings may include humpback whale watching.

“Food was good. We appreciated the captain steering us toward the whales. The music guy and hula gal did great. (The background for her dancing could have been better, maybe off to the side. Drinks need improvement too). We would recommend this to anyone…”

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7.Honolulu: Pacific Star Sunset Dinner Cruise and Show

★★★★★★★★★★4.5 · 633 reviews · 2 hours (approx.) · from $139

Board the Star of Honolulu at Pier 8 for a two-hour sunset cruise with a Pacific Rim buffet, one Mai Tai, coffee, tea, and live contemporary entertainment. You’ll see Oahu’s coast from wraparound decks, with an extra hour and fireworks on Friday sailings. Seats and show views vary by dining level.

“The food was so-so. The chicken was great but the beef was tough and the pork was dry. The entertainment was great, but should sign up as early as possible so you can sit closer to the stage and in the middle.”

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8.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 tableside dinner service, Hawaiian-style music, and an onboard bar. Choose prime rib, mahi mahi or other dinner options. Your first two alcoholic drinks are included, and winter departures may bring whale sightings.

“We had a blast! It was an experience you will remember for a lifetime! It was my husbands birthday and they sang happy birthday to him! The photographer took amazing photos! Everything was truly amazing!”

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9.Leila Na Pali Sunset Dinner Sail

★★★★★★★★★★4.5 · 524 reviews · 5 hours (approx.) · from $263

Sail from Port Allen Marina along Kauai’s Na Pali Coast aboard the 50-foot Leila. You’ll see towering cliffs, waterfalls, sea caves, and marine life, then enjoy a fresh dinner, open drinks, and a Champagne toast near sunset. Captain Kevin and crew members such as Jess, John, Nicole, and Max have all helped make recent trips memorable, though the crew changes.

“The layout of the boat made it tough to have the experience we were hoping for. For the cost of the experience I wish there was better seating and the fact it was too rough to sail was disappointing because the motor was loud. The crew was fantastic and very knowlegable. They really do a wonderful job with what they have. The coast was stunning once we got there and we even got to see a group of dolphins!”

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10.Maui Premium Sunset Dinner Cruise & Whale Watch

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

Sail from Maalaea Harbor on a three-hour Pacific Whale Foundation cruise with a four-course dinner, alcoholic drinks, sunset views, and live naturalist commentary. During whale season, keep watch for humpbacks, calves, dolphins, and underwater songs. Captain Andrew, Captain Chris, Stevie, and Ash are among the crew members praised for their warm, informative work.

“It was great experience. The crew member gave us a lot of info about the whale and we got to see 8 whales including a 3 weeks old baby whale”

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11.Maui Premium Dinner Cruise: Four Course Dining Experience

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

Cruise from Maalaea Harbor for about 2.5 hours as the sun drops over Maui. Pacific Whale Foundation serves four courses with a choice of chicken, short rib, shrimp, or Portobello mushroom. You’ll see Molokini, Kahoʻolawe, Lanai, and sometimes humpback whales. Bring a jacket, check in 45 minutes early, and expect a cashless boat.

“It was a beautiful boat ride. The food was delicious and everyone was excellent! Could not have asked for a better dinner cruise”

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12.Honolulu Sunset Dinner Cruise with Friday Fireworks Show

★★★★★★★★★★4.0 · 285 reviews · 2 hours 30 minutes (approx.)

You’ll cruise from Honolulu along Waikiki Beach toward Diamond Head, dine on beef short ribs or fresh mahi-mahi, and watch Friday’s Hilton Hawaiian Village fireworks from the water. The crew includes staff such as Alex, Lili, Lucy, and Jessica. Bring your own alcohol for the onboard mixologist, and arrive early if you want a better upper-deck seat.

“Great staff and food. Would do it again! The views were great also. Very well organized. Would recommend”

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

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

Sail from Ma’alaea Harbor for two hours aboard Calypso Molokini Charters’ triple-decker catamaran. Enjoy live music, two alcoholic drinks, sunset views of Maui, Lanai, Kaho’olawe, and Molokini, plus a choice of prime rib, mahi-mahi, chicken, ribs, or vegetarian pasta. Whales may appear from December through April.

“It is a memorable birthday celebration for my husband.”

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14.Historical Dinner Cruise Tour to Kealakekua Bay

★★★★★★★★★★4.8 · 198 reviews · 3 hours · from $199

Spend three hours aboard Body Glove Cruises, sailing from Kailua Pier along Kona’s coast to Kealakekua Bay. A local historian explains sites linked to Captain Cook, King Kamehameha, and Hawaiian traditions while you enjoy live slack-key music, dinner, one complimentary drink, and sunset views.

“great live music, great staff, great drinks. and we saw whales”

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15.Honolulu: Sunset 5 Course Dinner Cruise with Entertainment

★★★★★★★★★★4.4 · 28 reviews · 2 - 3 hours · from $193

Sail from Honolulu for a two-hour sunset dinner cruise with five courses, Maine lobster, tenderloin steak, two premium beverages, Hawaiian and jazz music, and the Moku Ola show. You’ll see Waikiki, Ala Moana, and Diamond Head from four decks, including an open observation deck. Optional Waikiki pickup is available.

“I enjoyed it, our server seemed a bit scatter brained and the tables were definitely set up in a way that was not ideal for where we were sitting. But the upper deck of the boat was really nice and seeing the sky and the coast from the boat as the sun went down was super beautiful. The food was really good. I think the circumstances of seating location and the server being a bit overwhelmed was probably the worst part of it.”

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