Maui Dinner Cruise

The fresh sea air and bright blue waters draw many to the shores of Maui – and some of these visitors really cause a splash. These mighty wanderers, best known as humpback whales, breech, splash, and swim through the ocean with a surprising grace for animals that can weigh in at 45 tons.

When the Calypso Maui dinner cruise sets sail on whale-watching tours, the captain and crew ensure that passengers have the best view of the whales. When Destination360’s Dan Taylor took a cruise, it didn’t even take 10 minutes to spot the first whale and calf. These amazing creatures lingered for a while, as did the stunned passengers.

“The captain was kind enough to move the vessel around so everyone had a chance to view,” he said. “During the sailing we encountered at least 10 whales, some of which popped up rather close to the vessel. We saw several pec slapping, many tails, a breach, and numerous whale spouts.”

Whale Watching Dinner Cruise

Like the time that Destination360's group enjoyed their outing, Calypso passengers are treated to a warm welcomes by the affable crew, plus chef-created meals, and plenty of time to enjoy the scenery. The islands of Lanai and Kaho’olawe stretch out in the distance, and it’s easy to spot the legendary snorkeling site, the Mokokini Crater from the decks of the motorized catamaran.

With three decks, glass-bottom panels, and shaded cabins, the Calypso Maui is well-suited for whale-watching excursions and other outings. This catamaran sets sail from the South Ferry Dock in Wailuku—a centrally located small town just to the west of Kahului and Maui’s main airport. In addition to seasonal whale-watching tours, Calypso Maui welcomes passengers aboard for Maalaea and Lahaina dinner cruises, snorkeling tours, and private charters. Cruises are available year-round, with the whale season taking place between December and April.

Dinner Cruise Group in Maui

Cruise Lobster Menu Option

For the Destination360 group, the check-in process for his whale-watching trip was straightforward by providing a voucher number or a last name. “One thing to keep in mind is seating is first come first serve," Taylor said. "So if you’re particular about getting a certain seat, then arrive early. If you’re prone to sea sickness select a select down low and in back, if you want the best views but exposed most to the elements then select the front. We choose the 2nd level in back which gave us shade, some wind block, and still excellent views. It was near enough the excellent solo musician who played great tunes.” 

After everyone settled in for their Maui dinner cruise, the friendly staff came around took drank and confirmed food orders. When reservations are made, passengers can choose what meal options sounds best. “Our group chose lobster, prime rib, and fish,” Taylor said. “The lobster was a big 8oz portion, the prime rib was on the smaller side but excellent quality, and while we didn't have the ribs they seemed to be the biggest plate of the food if you're a hungry meat eater. One thing to note is they don't have specific gluten free dairy free options so ask the chef what each side dish is made with.”

Maui Dinner Cruise Sunset

Sunset Maui dinner cruises are available year-round, with the best chance to see whales happening from Christmas Eve to April 15. The evening Destination360 set sail, the weather was perfect, he said. “We would highly recommend Calypso if you’re looking for a Maui dinner cruise.”

The Calypso Maui, offering Maalaea and Lahaina dinner cruisesresides at Slip 82 at the South Ferry Dock at 101 Maalaea Road, Wailuku, HI, 96763. Check out Calypso Maui for more details about this Maui dinner cruise. Parking is available on the pier in front of the vessel, which costs a few dollars for 2-3 hours. If you save extra time before the cruise, you’ll have the chance to stroll around and watch for turtles and whales in the distance.

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