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Mon, Jan 15


Maalaea Bay

The Monday After Party Sunset Cocktail Whale Cruise on the Calypso

Join the Race Director and Race Committee for a post race get together with runners and families on the Calypso. ​ Cocktails, dinner, and live music and probably whales to watch These are private charters for runners and family or friends and you must text Jenn at the Calypso to book. 808-283-6764

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The Monday After Party Sunset Cocktail Whale Cruise on the Calypso
The Monday After Party Sunset Cocktail Whale Cruise on the Calypso

Time & Location

Jan 15, 2024, 4:30 PM – 7:00 PM HST

Maalaea Bay, 101 Maalaea Rd, Wailuku, HI 96793, USA

About the event

Location: Slip 82, South Ferry Dock 101 Ma’alaea Road, Wailuku, HI 96793

To Register you must Text Jenn at the Calypso to Reserve (808) 283-6764.

International reservations should email:

Time Differences: +++Maui time: 8AM, West Coast time 11AM, East Coast 2PM

Adults (13-99): $TBA

Book the Maui Oceanfornt Marathon 2023 dinner cruise on Calypso boat, Sunday 1/15/23 or  Monday 1/16/23, 5-7 pm, has a check-in at 4.30 pm, at Maalaea harbour.

Each cruise will take 80 paying passengers,  Price $TBA, including discount, taxes & fees.

Menu choices include prime rib, with horseradish sauce & au jus , fish (mahi-mahi or ono, breaded, with lemon butter sauce), baby back ribs, BBQ boneless chicken breast, or vegetarian option, penne pasta with Thai basil marinara sauce.

All Options Include: Caesar Salad with homemade croutons and fresh shaved parmesan cheese. Jasmine infused white rice. Vegetable medley. Soft bread sticks. Dessert choice between chocolate cake or New York style cheesecake. two cocktails included, unlimited sodas, juices & water.

Guests should call/TEXT Jennifer Clarke, private charter agent for Boss Frog/Calypso charters, 808-283-6764


Ma’alaea Premier Dinner Cruise!!

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 live 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 on-board 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. dWhen 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!

Check out the entire menu below, and please know – our chef is happy to accommodate special dietary restrictions. Just tell us what your needs are when you book your tickets. If you forget to say something at that time, last minute changes must be submitted with Reservations by noon on the day of your tour at 808-661-9937.

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

We’ll sea you soon on Calypso!

Meal Options:

  • 8oz Lobster Tail: (Currently unavailable.) Baked onboard during the charter so it’s served HOT & delicious sided with drawn butter & lemon.)
  • Surf & Turf: (Currently unavailable.) 8oz Lobster baked onboard during the charter so it’s served HOT sided with drawn butter side by side to your Hawaiian Slow Roasted Prime Rib served with horseradish and au jus! THE Elite Hawaiian dinner option – from Mauka (Land) to Makai (Sea)!
  • Hawaiian Slow Roasted Prime Rib: Hand carved to order by 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: Cheese Tortellini w/ sautéed green/red peppers & served with a creamy alfredo sauce.
  • All Options Include: Caesar Salad with homemade croutons and fresh shaved parmesan cheese. Soft Hawaiian dinner rolls with butter.
  • Dessert choice: Either a delicious Chocolate Cake or New York style cheesecake!
  • *Dietary Restrictions: Vegetarian & Gluten-Free meals can be made available only upon request when booking reservation.*


  • Mai Tai: Light + Dark Rum, Guava, Pineapple & Splash of Cranberry.
  • Pina Colada: Light Rum, Coconut, Pineapple, Splash of Dark Rum. *Served on the rocks*
  • Margarita: Silver Tequila, Sweet & Sour, Splash of Orange Juice. *Served on the rocks*
  • Dark ‘N’ Stormy: Dark Rum, Ginger Ale & Splash of Bitters.
  • Tequila Sunrise: Silver Tequila, Orange Juice & Cranberry.
  • Vodka Soda Spritz: Vodka, Soda Water, Spritz of Your Choice (Guava or Pineapple).
  • Local Beers: Maui Brew Co. “Bikini Blonde” & Maui Brew Co. “Big Swell IPA”.
  • Wine: Chardonnay & Cabernet.

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