2.5 Hours
Maalaea Harbor, Maui
Seasonal 4:30PM or 5:30PM
Tour Times

UPDATED 2021: Description of activity subject to change without notice due to new limitations and updated capacities. Thank you.


  • Availability: Daily
  • Tour Times:
    • Summer Schedule: (April 16th – October 14th)
      Check-in: 5:30 PM
      Departures: 6:00 PM
      Return: 8:00 PM
    • Winter Schedule: (October 15th – April 15th)
      Check-in: 4:30 PM
      Departures: 5:00 PM
      Return: 7:00 PM
  • Duration: 2 Hours 30 Minutes (approx)

Are you looking for the best sunset views Maui has to offer? Consider the Calypso dinner cruise. This stable, comfortable, triple-deck catamaran leaves from centrally-located Ma’alaea Harbor. The relaxing two-hour excursion gives you time to enjoy a delicious meal, explore the incredible craft, listen to great island music, and watch the sun go down from your place on top of the waves! Seating on the Calypso dinner cruise comfortably accommodates any size group, including couples, families, and even large corporate events. You’ll find 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 need to fidget.

Explore all three decks, and take your time to find just the right spot in sun or shade. Calypso’s three restrooms are on the lowest deck. The front of the boat is the most open to sun and wind, so wear a secure hat and, as one of our lighthearted guests advised: consider leaving your fake eyelashes on shore! After you’ve settled in, pick up a fizzy soda, tropical juice island theme adult beverage. Your Calypso dinner cruise includes two free drinks, and 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.

When it’s time for the delicious main meal, our 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. While you chow down, the crew comes by often to take things out of your way, ensuring that no trash ends up in the ocean. There is plenty of time to gaze at the islands of Kaho’olawe and Lanai in the distance – not to mention the epic snorkeling site Molokini Crater. Closer to the boat, you’ll see the Kahalawai Mountains of west Maui as they stretch toward the sky. When humpback whales are visiting the Islands from Alaska, chances are excellent that you will see some of the magnificent marine mammals on your Calypso dinner cruise! Any time you do, the captain and crew are sure to get on the mic for some whale conversation. You and your group will love this fun time on the sea, so follow the sun, love your loved ones, and have a great meal on the Calypso dinner cruise!

**Food not included for free kids. Must purchase child’s ticket to include food.

Location: Ma’alaea Harbor, Slip #82
Address: South Ferry Dock, 101 Maalaea Rd, Wailuku, HI 96793
Google Maps: https://goo.gl/maps/iVGq13dS8WgCFubR9

Parking is $0.50/hour. Pay for 6 hours ($3.00). You can pay in cash or with a credit card.

Check-in: Please check-in 30 Minutes prior to your tour time.

Special Notes:

  • Guests need to fill out the Liability Waiver before checking in, or check-in may be delayed.
  • Kids 3 & under are free – (1) per paying adult. Additional kids (3 & under) must purchase a child ticket.
  • 2 alcoholic drinks included. Beer is provided by Maui Brewing Company. Wine, mai tais, and well drinks. Additional alcoholic drinks are $5.
  • Our chefs do their best to accommodate guests with food allergies. Please tell us what your needs are when you book your seats.
  • All special requests must be received at least 24 hours before your scheduled cruise.

Activity Company: Boss Frog's Calypso

Dinner Menu Meal Options:

  • Hawaiian Slow Roasted Prime Rib: Hand-carved to order by the onboard chef, served with horseradish, au jus & other condiments available.


  • Baby Back Ribs: Our award-winning, meaty, mouthwatering ribs are slow-smoked in a rotisserie smoker over kiawe and guava wood. We baste our ribs in our homemade sweet & tangy BBQ sauce sealing in the moisture and adding a tender crispy “bark” to the outside!


  • Smoked Chicken: Plump whole chickens are seasoned or “rubbed” with our homemade dry rub and using a custom stand are placed in our rotisserie smoker. We slow smoke the chicken using our combination of Kiawe and guava wood until the skin is crispy golden brown & the chicken swells with moisture steaming from inside. In addition, the moist chicken absorbs the flavor from the kiawe and guava woods!


  • Local Island Fish: Delicious local island fish (usually Mahi-Mahi or Ono) served with fresh lemon, & savory caper beurre blanc sauce. Mmm!


  • Vegetarian Option: Pasta Primavera using Cheese Tortellini w/ sauteed green/red peppers & served with a creamy alfredo sauce!


  • Vegan Option: Sliced Zucchini topped with sauteed mushrooms, onion, tomato & served with marinara sauce!

All Options Include:

  • Caesar Salad with homemade croutons and freshly shaved parmesan cheese.
  • Mashed potatoes and gravy. 
  • Vegetable medley.
  • Soft Hawaiian dinner rolls with butter.
  • Dessert choice: Either a delicious Chocolate Cake or New York-style cheesecake!

2 alcoholic drinks included. Beer is provided by Maui Brewing Company. Wine, mai tais, and well drinks. Additional alcoholic drinks are $5.

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

*Dietary Restrictions: Vegetarian & Gluten-Free meals can be made available only upon request at least 24 hours before your scheduled cruise.*