2.5 Hours
Maalaea Harbor, Maui
Tour Times

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.


  • Availability: Daily
  • Tour Times: 5:30 PM
  • Duration: 2 Hours 30 Minutes (approx)

Location: Ma’alaea Harbor, Slip 76 – 78
Address: South Ferry Dock 101 Ma’alaea Road,, 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:

  • Rosemary Garlic Roasted Prime Rib 


  • Fresh Mahi Mahi w/ Lemon Butter Caper Sauce


  • Vegetarian option: Penne Pasta w/Fresh Thai Basil Marinara


  • BBQ Roasted Chicken Thigh Leg Combo


  • Kiawe Smoked Baby Back Ribs

All Options Include:

  • Caesar Salad, Homemade Buttery Crouton, Warm Breadstick, Fresh Parmesan
  • Freshly Sourced Veggies Sauteed 
  • Desserts: New York Style Cheesecake or Double Layer Chocolate Cake 


  • Soft Drinks 
  • Juice-Passion, Orange, Guava 
  • Water 
  • Adult Beverages 
  • Hot Coffee/Tea

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 when booking reservation.*