Calypso Dinner Cruise – Prime Rib or Island Fish!

With views of Kaho’olawe, Lana’i, and Maui, this dinner cruise brings the enchantment and magic of the Islands to life.

No online bookings within 48hrs of activity date.
If you would like to book within 48hrs, please call (808) 856-4274.

sStaff Favorite

Don’t miss the Calypso Dinner Cruise. Prime Rib or Island Fish!

Are you looking for a truly unique dinner venue on Maui? How about the Calypso dinner cruise? Relax and have fun aboard the island’s only three-deck catamaran. Over 4000 square feet of table seating and three restrooms await on this large, stable vessel. You can simply kick back and take in the 360-degree sunset views. Checking in at Ma’alaea Harbor is a sea breeze, too, because parking is easy and low cost.

Say aloha to your captain and crew as you step up easily onto the boat, and find the perfect seat. Enjoy some hors d’oeuvres while everyone gets settled in. You will spend two and a half hours on the water while the sun sinks into the sea, turning the sky around you any number of lovely colors.

The Calypso dinner cruise is great for couples, as well as groups of any size. Large tables for eight are in the shaded areas near the center of the boat. More intimate seating – tables for two and also for four, is ready for you and your sweetie along both sides of every deck. If anyone would like to work on their tans, make sure to sit at the front of the second deck, or go up onto the third; both areas are open to the gorgeous island sky.

Once you have enjoyed the appetizers – delicious chicken and vegetable pot stickers as well as raw vegetables with dip – the dinner is fabulous. You will have your choice of succulent prime rib, teriyaki chicken grilled with pineapple, light and tasty mahi mahi (fish), or a vegetarian option. Sides include dinner rolls with plenty of butter, Caesar salad with Parmesan cheese, a great mix of vegetables, and roasted rosemary potatoes. And don’t forget—there’s chocolate cake for dessert!

A local live musician sets the mood throughout the Calypso dinner cruise with hits from the 1940s to today. One of the crew members has a beautiful singing voice, too, and when the spirit moves her, she will pause in her duties to join in! Feel free to dance in your seat or simply listen to the music — whatever floats your boat.

Tableside drink service allows you to enjoy your delicious meal, the unbeatable ocean views, and your fabulous company without interruption. Currently all alcohol is BYOB.

The Calypso dinner cruise is a lot of fun. Many folks enjoy this special excursion on their last night on the island, or to commemorate unique occasions such as birthdays, anniversaries, and engagements. Children six and younger ride and eat free (one child for each paying adult), so why not come aboard? You’ll love it!

Our chefs do their best to accommodate guests with food allergies.  Please tell us what your needs are when you book your seats.

The Calypso dinner cruise is available on Monday, Wednesday, Friday, and Sunday evenings.

Departs from Ma’alaea Harbor, Slip #82.
October 1st – April 30th Check-in time is 4:00 pm returning at approximately 7:00 pm.
May 1st – September 30th Check-in time is 4:30 pm returning at approximately 7:30 pm.
101 Maalaea Boat Harbor Road, Wailuku HI 96793
For help call Maui Activities at 808-856-4274