Sunset Dinner Cruise

Molokini Snorkel CalypsoCalypso Dinner Cruise 146Calypso Maui - Maalaea Sunset Dinner Cruise (Smiling Couple)Calypso Maui - Maalaea Sunset Dinner Cruise (Calypso Maalaea)Calypso Maui - Maalaea Sunset Dinner Cruise (Maalaea Sunset Boat)Calypso Maui - Maalaea Sunset Dinner Cruise (Calypso Logo)Calypso Maui - Maalaea Sunset Dinner Cruise (Menu)Calypso Maui - Maalaea Sunset Dinner Cruise (Food)
Calypso Maui Breakfast 144
Molokini Snorkel Calypso
Calypso Dinner Cruise 146
Calypso Maui - Maalaea Sunset Dinner Cruise (Smiling Couple)
Calypso Maui - Maalaea Sunset Dinner Cruise (Calypso Maalaea)
Calypso Maui - Maalaea Sunset Dinner Cruise (Maalaea Sunset Boat)
Calypso Maui - Maalaea Sunset Dinner Cruise (Calypso Logo)
Calypso Maui - Maalaea Sunset Dinner Cruise (Menu)
Calypso Maui - Maalaea Sunset Dinner Cruise (Food)

Calypso Maui – Maalaea Sunset Dinner Cruise

$119.95 BOOK NOW

Best Price Guarantee

Calypso Impresses with Dining Options and View

This beautiful Maui dinner cruise departs from Maalaea Harbor and is on a stable, comfortable, triple-deck catamaran known as the Calypso. This enjoyable two-and-a-half-hour excursion gives you time to listen to great live music while having a wonderful evening meal watching the sun fade into the horizon! The Calypso Dinner Cruise comfortably accommodates groups of any size, it’s great for couples. large events, or families. Tables vary in size and are able to accommodate two, four, eight, and ten, as well as extra space to lounge. You’ll see the ocean with a new perspective on the Calypso Dinner Cruise. Take time to explore all three decks, the front of the boat is the sunniest and you’ll wanna bring your shades. Once you’ve gotten situated on board, appetizers and drinks will begin. This Calypso Dinner Cruise comes with two free drinks, and once the catamaran has motored out of the harbor, you can order alcohol. Very attentive crew members tend the bar, and they can bring you anything you like. After dinner step up to the beat of our Favorite Island Music and dance the night away on the dance floor. 

Choose Your Entree

  • Prime Rib with Au Jus and Horseradish Sauce
  • Baby Back Ribs: Our 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.
  • Smoked Half Chicken(Drunken) with Sweet and Mild BBQ Sauce
  • Grilled Mahi-Mahi on a Bed of Spinach and Tomatoes Topped with Lemon Caper Butter
  • Veggie Option: Cheese Tortellini with sautéed green/red peppers & served with a creamy alfredo sauce

Also includes salad, sides, desserts, and drinks!

Salad: Caesar Salad with croutons and parmesan cheese, dinner rolls

Sides: Sautéed mixed veggies, wild rice pilaf, mashed red potatoes with mushroom gravy.

Dessert: Chocolate cake with chocolate frosting.

Drinks: Fully stocked bar with your choice of Hawaii’s best tropical drinks including Mai Tai’s Pina Coladas, and everything else! First two are free!

Advance Reservations Required



Calypso Dinner Cruise - Sunset Special

  • Best Price Guarantee
  • E-Ticket Delivery
  • Free Cancellation
per Adult $119.95

Ages 13 and Up (7.00 Fuel Surcharge Applied in Checkout)

Ages 4-12 (7.00 Fuel Surcharge Applied in Checkout)

Ages 0-3 (Lap Only - No Meal)

Please specify details

Entree Choice Each Passenger

Total $0.00

Calypso Maui Dinner Cruise Details

Departs Maalaea Harbor Slip #82
GPS: 300 Maalaea Road, Wailuku Hawaii 96793

Maui Tickets For Less Cancelation Policy:
A 72 hours notice is required for a refund. Only exception is a note from a local doctor.
No-shows” will be charged full.

Advance Reservations Required

Days Available:
Monday, Wednesday, Friday

Times: Check-in 4:00pm, Departs at 4:30pm
Return 7:00pm
April 1st – September 30th Check-in 4:30pm, Departs at 5:00pm
Return 7:30pm

Check-in 30 minutes prior to activity start time.

Duration: 2.5 Hours


Need Help?

(808) 856-3500

Calypso Dinner Cruise
Based on 42 reviews
Liz H.
Liz H.
Great dinner cruise and crew! The food wasn't bad either. We saw a bunch of whales too, such a great bonus! The captain let my little guy drive the boat, he...
Hannah M.
Hannah M.
The first hour was a 2-3 star experience. After that it was 4-5 stars. To compromise, I'm giving this 4 stars.Here's the rundown:The notes said there...
Christine N.
Christine N.
Omg everyone should experience it they had one heck off a crew my daughter was getting anxiety and was panicking kelly rushed over and help so fast she even...
Bob K.
Bob K.
Our party of six had a GREAT TIME aboard the Calypso last night! The crew helped us celebrate our anniversaries as we renewed our wedding vows together....
Renz L.
Renz L.
Needed a fun, semi-casual activity for 5 adults + 4 kids under 5 and this was perfect! I was weary bc we get seasick easily but the boat was a 3 level...
Ren L.
Ren L.
We had an awesome time tonight with Captain Karl and crew. Food was good. Drinks were great and the views and commentary were outstanding!
Julia A.
Julia A.
First off a special thanks to Capital Karl... he was the sweetest and most helpful person. He called us from our car to make sure that my family and I were...
Jason M.
Jason M.
We had a great time! We saw a ton of wales and had a great meal. Covid sucks and makes everything difficult but the crew did a great job in spite of it. We...
Danny Matranga
Danny M.
Best place to rent from. They were very helpful and then equipment was the best I’ve used in Maui. Highly recommended. Very friendly and informative. Thank you.
Melonie K.
Melonie K.
It didn't take us to Ogygia but was fun nonetheless sitting on top deck and stargazing was one of my favorite things. The staff was super friendly and...
Toby Levitt
Toby L.
I rented and bought some snorkel gear from Brad. He was fantastic to work with. I have been here many times and this is the best store on Maui to rent or buy stuff from.
Steven Martin
Steven M.
Centrally located. Decent equipment prices are Competitive. Friendly and Knowledgeable staff.
Juliette F
Juliette F
The staff is very friendly. The availability of equipment was awesome. I had an issue with an underwater camera but was contacted by the owner and was offered a refund. This is a very professional business that cares that people are happy. Thank you Boss Frog's, I will be returning!
Martha J.
Martha J.
We scheduled this a few days out and the day we went it was overcast so we did not get the Sunset we were expecting, but it was a very nice evening and we...
Latasha K.
Latasha K.
First of all...the food....if you opt for that.. is ONO!!!!!! My boyfriend had the prime 8 year old the fish..and me... LOBSTER TAIL....of course...
James Skinner
James S.
Orron hooked us all up. Educated us on the dangers and suggested great places to go. Hooked my wife up with magnified goggles so she could see!! Great place!!

Questions? Call Maui Tickets for Less (Toll Free) 855-268-0387