Calypso Dinner Cruise | Reg $139.95 | Special $119.95!

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This is our favorite dinner cruise.  The Calypso is Maui’s finest catamaran. If you have any questions about their dinner cruise, please don’t hesitate to give us a call! As Maui’s top rated rated rental shop, you can be certain our customer happiness superheroes will help guide you through the process and answer any questions you may have! Mahalo!

(808) 298-3021

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  • Guaranteed Safe Checkout
  • No Booking Fee
  • No Credit Card Fee
  • E-Ticket Reservation Delivery
  • Free Activity Cancellation
  • Easy Rental Gear Return

The Calypso sunset dinner cruise is the perfect way to celebrate any special occasion with your significant other! Instead of  booking another dinner reservation consider an evening on the water on Maui’s premier catamaran! Come aboard this stable, comfortable, triple-deck catamaran and enjoy sensational sunset views while sipping a tropical cocktail and listening to local live musicians. The meals are delicious and the desserts are decadent.

When the humpback whales are visiting from Alaska from November through April chances are excellent you will encounter them and your dinner cruise just turned into a whale watch 😉

There are tables for two, four, eight, and ten, as well as enclaves throughout the vessel to sit and sip drinks, see the ocean from a new perspective, or hang with the kids when they are feeling rambunctious and there are 2 loo’s on the boat.

The Calypso dinner cruise is our personal favorite. We’re sure you’ll have an incredible time so book your tickets today!

Pricing: Reg Adults $139.95

  • Adults (13 years and older) $119.95 plus tax 
  • Children (4 years to 12 years old) $94.95 plus tax
  • Young Children / Infants (3 years to 0 years old) $0 Free
  • Best Price Guarantee

Check-in: 4:30pm at Ma’alea Harbor 

Depart: 5:00pm

Return: 7:30pm

Available Days:

  • 7 Days Per Week

Cruise Duration: 2.5 Hours

Calypso Sunset Dinner Cruise Location: Ma’alaea Harbor, End Of Main Jetty, Slip 82 101 Ma’alaea Road, Wailuku, Hi 96793

GPS Address: 101 Ma’alaea Rd, Wailuku, Hi 96793

Vessel Details:

  • Spacious 3 decks
  • 3 flushing restrooms on lower deck
  • Bar
  • Plenty of seating throughout
  • 70′ Tripple Decker Catamaran, Stable and Fast

Included with your Calypso sunset dinner cruise:

  • Two free drinks (once the catamaran has motored out of the harbor you can order alcohol). Friendly crew members tend the bar, and they can bring you mai tais, blended drinks, wine, and beer. Cash bar after your first two free drinks.
  • Meal
  • Dessert
  • Live Music

Check-in outside the vessel in the Ma’alaea Harbor. Once you’ve settled into your chosen seats (1st come), pick up a fizzy soda, tropical juice, or an island theme adult beverage. When it’s time for the delicious main meal,  onboard chef Keoni carves the juicy prime rib. Mahi Mahi, teriyaki chicken, steamed vegetables, roasted potatoes, and chocolate cake is also ready for you to eat.  

Calypso Sunset Dinner Cruise Meal Options:

  • Baby Back Ribs: The Calypso sunset dinner cruise’s award-winning, meaty, mouth-watering baby back ribs are dry-rubbed and slow-smoked in our rotisserie smoker over a special mixture of kiawe and guava wood. We mop (or baste) our ribs while cooking with our homemade sweet and tangy BBQ sauce, sealing in the moisture and adding a tender crispy “bark” to the outside.
  • Drunken Chicken: Plump whole chickens are seasoned or “rubbed” with our homemade dry rub and, using a custom stand, are placed in our rotisserie smoker with a can of Maui Brewing Company’s Coconut Porter inside the chicken. We then slow smoke the chicken using our combination of kiawe and guava wood until the skin is crispy golden brown and the chicken swells with moisture from the beer slowly steaming from inside. The moist chicken absorbs the flavor from the kiawe and guava woods, too.
  • Hawaiian Slow-Roasted Prime Rib: Hand carved to order by our onboard chef with horseradish and au jus
  • Delicious Sautéed Island Fish (Mahi or Ono) lemon caper butter sauce served on a bed of spinach with tomatoes and onions.
  • Vegetarian options are available as well.

All Options Include:

  • Mashed potatoes.
  • Two free alcoholic drinks.
  • Caesar salad with Parmesan cheese and cracked pepper.
  • Vegetable medley.
  • Fresh dinner rolls with butter.
  • Ridiculously good chocolate cake.

The chef is very good at adjusting the menu for guests with food sensitivities and/or special diets.  When you book your seats, let us know what you need in the notes.

“This is me and Guinevere’s favorite date night out. The Calypso Dinner cruise is an awesome value for a super romantic, yummy, and enjoyable night out.”  ~Mark Noble, owner


Calypso Sunset Dinner Cruise Meeting Location

Ma’alaea Harbor, End Of Main Jetty, Slip 82

101 Ma’alaea Road, Wailuku, Hi 96793



Rental Pickup Location Map

Map is not available.