Calypso Dinner Cruise

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

Due to high demand and limited capacity,
please call (808) 856-4274, and we will personally assist you.

sStaff Favorite


Don’t Miss The Calypso Dinner Cruise. Choose Lobster Tail, Prime Rib, Fish, BBQ Chicken, Baby Back Ribs Or Vegetarian entree.

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. You will spend two 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.

You pick your choice of succulent prime rib, lobster tail, light and tasty island fish, drunken BBQ chicken, finger lickin baby back ribs or a vegetarian option. Sides include dinner rolls with plenty of butter, Caesar salad with Parmesan cheese and cracked pepper, a great mix of vegetables, and mashed potatoes. And don’t forget—there’s chocolate cake or cheesecake for dessert!

A local live musician sets the mood throughout the Calypso dinner cruise with hits from the 1940s to today. 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. 

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 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, and Friday evenings.

Departs from Ma’alaea Harbor, Slip #82.
September 16th – April 15th Check-in 5:00 pm, return 7:30 pm.
April 16th – September 15th Check-in 5:30pm, return 8:00pm.
101 Maalaea Boat Harbor Road, Wailuku HI 96793
For help call Maui Activities at 808-856-4274