From Ma’alaea Harbor: Sunset Dinner Cruise Aboard Calypso

130 Reviews

Experience The Real Hawaii!

Book online or call: (808) 698-5779

Tour Overview

Hawaii is a major destination for relaxation and fun times—and this Maui sunset dinner cruise allows you to let loose and enjoy yourself while visiting the island. Step aboard a ship that cruises by the Na Pali coast, and take in views during sunset as you feast on your dinner of choice. Dance to live music, sip on two free drinks from a full bar, and create your own memorable experience on the water.


  • Tour Name: From Ma'alaea Harbor: Sunset Dinner Cruise Aboard Calypso
  • Availability: 7 Days A Week
  • Duration: 2h
  • Start Time: 5pm

What's Included

  • Dinner Options: (Depending on your Entrée selected) Fresh Fish, Kiawe Smoked Chicken, Baby Back Ribs, Prime Rib or Vegetarian
  • Island-Style Music
  • Your first 2 alcoholic drinks are free, and only $3 thereafter
  • Soda/Pop
  • Restroom on board
  • Experience Captain & Crew
  • Tableside Service
  • Entry/Admission – Calypso
What’s not included
  • Hotel pickup and drop-off – NOT INCLUDED
  • Gratuities / Tips
  • Paid parking is avail in front of Maui Ocean Center ($2/hour or $8/5hours)

What to expect

Itinerary
This is a typical itinerary for this product

Stop At: Calypso, 101 Maalaea Rd Slip 82, South Ferry Dock, Wailuku, Maui, HI 96793

Join us aboard the only 3-story Power Catamaran in Hawaii – and enjoy a wonderful sunset with a table-side serviced experience!

Duration: 2 hours

Departure and return

Departure details

101 Maalaea Rd, Maalaea HI 96763
SLIP 82

MANDATORY CHECK-IN: 30 minutes prior to departure

Return details

Returns to original departure point

Accecibility

  • Wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Transportation is wheelchair accessible
  • Surfaces are wheelchair accessible

Additional Information

  • Confirmation will be received at time of booking
  • MEAL SELECTION: If members of your group want different menu options, you will need to make separate reservations, once complete please reach out to our team so we can ensure you are seated together.
  • Operates in most weather conditions, please dress appropriately
  • A 48-hour notice is required for cancellation or reschedule.
  • Most travelers can participate
  • Mandatory Check-in 30 minutes prior to departure.
  • Children must be accompanied by an adult.
  • Minimum drinking age: 21 years old.
  • Bring cash if you’d like to tip the crew!
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
  • This tour/activity will have a maximum of 80 travelers

Cancellation Policy

For a full refund, cancel at least 24 hours in advance of the start date of the experience

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Adult - Baby Back Ribs $139.95
Adult - BBQ Chicken $139.95
Adult - Fish $139.95
Adult - Prime Rib $139.95
Adult - Vegetarian $139.95
Child (4-12) - Baby Back Ribs $109.95
Child (4-12) - BBQ Chicken $109.95
Child (4-12) - Fish $109.95
Child (4-12) - Prime Rib $109.95
Child (4-12) - Vegetarian $109.95
Small Child (0-3) 0

What others are saying...

Gary E. Avatar
Gary E.
1 star rating
10/01/2025
Not worth the money The prime rib state was not cooked. I had to send it back. The drinks consisted of cheap alcohol. The music was bad. All in all not worth the 300 for 2 people.
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Danielle Avatar
Danielle
Lakeland, FL
5 star rating
9/22/2025
Excellent experience and great staff Great experience. Great staff. The photographer was mediocre though. For the prices she was charging and the horrible photos she took, it was not worth it.
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Heather K. Avatar
Heather K.
3 star rating
9/20/2025
Meh.. The instructions to get there are very clear. I appreciated the suggestion on what time to leave depending on where you are staying. The night we cruised, it was extremely windy. They said it’s the windiest harbor there is but I’m not sure if it was extra windy that day or if that was termed normal. They closed the ship up since it was so windy so your food didn’t fly away, I appreciated that. However, they had to cram a lot of people on to the 2 floors where it was enclosed. This resulted in not enough elbow room and you’re packed like the sardines during your dinner. They also sat you next to your guest rather than across from them. I suggest sitting your guests across from each other so you can have a natural conversation rather than turning to talk to your guest. And that way you’re not facing a stranger which was kinda awkward. Unfortunately, the prime rib was pretty bad. It was grey, overcooked and the horseradish wasn’t spicy at all. The gravy they smothered it in was pretty bad. The grilled vegetables were the best part! The drinks were okay. They did the best they could on a boat. I know the wind is out of their control, I just wish they would’ve opted to reschedule because the wind made it impossible to enjoy the cruise to its fullest, but again, maybe the wind is normal and I’m just being dramatic. I don’t think the cruise is worth $150 a person. I would’ve rather booked a catamaran and then had a fancy dinner.
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Gina M. Avatar
Gina M.
Middletown, OH
5 star rating
9/13/2025
Wonderful sunset cruise Such a wonderful experience from the food to the wonderful service and Captain Steve and songs by Christina. And of course the great Maui sunset. Highly recommend
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NorthStar16200699655 Avatar
NorthStar16200699655
5 star rating
9/05/2025
Charming. This was a beautiful cruise, slow and easy going though a few people did get seasick, the crew was ready with dramamine and ginger ale. We got seated up front with an amazing view and there was Live Music, not a recording. Captain Kiwi was attentive to the guests throughout the trip and was funny, keeping the cruise entertaining. The crew was helpful and continually checked on everyone so we didn't feel like e lacked anything. The meal was perfectly prepared with dessert closely following and was satisfying. Would recommend.
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Janet B. Avatar
Janet B.
Austin, TX
5 star rating
8/18/2025
Maui 2025 It was a very nice evening. The staff were great, very friendly and helpful. Enjoyed the live music, Christina was very good, with nice folk music that added a nice atmosphere to the trip. The food was good and the whole vibe was very relaxed and we enjoyed it all
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Travel589735 Avatar
Travel589735
3 star rating
8/03/2025
Dinner on a boat. It would be much more enjoyable if it was more of a cruise rather than going to a spot and staying until after the sunset. The food was NOT very good. Had the mahi mahi and I've had MUCH better. Staff was great!! They certainly did their part!
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MAJ D. Avatar
MAJ D.
5 star rating
7/31/2025
Sunset Dinner Cruise in Maui Our sunset dinner cruise on the Calypso was even better than expected. My wife and two small kids rated our trip a 8.5/10. The experience was amazing. We traveled along the Maui coastline and were treated to breathtaking views! The 2-hour journey included a 3-course meal and two complimentary cocktails. The meal options were delicious and well portioned. The crew was fantastic. They were all attentive and friendly. The onboard photographer captured wonderful moments for each traveler to enjoy. This is an absolute must try when visiting Maui!
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Bonnie D. Avatar
Bonnie D.
1 star rating
7/21/2025
The Maui Harbor is one of the roughest in the world, according to the captain’s announcement on the ship. If I had known that beforehand, I wouldn’t have booked the trip. The crew was nice. They did their best, but the ship pitched so much that we couldn’t enjoy or even fully eat our meal. The route was dull and the sunset was unimpressive due to cloud coverage. Not a fun trip.
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thomas h. Avatar
thomas h.
1 star rating
7/11/2025
Would book something else. We ended up getting seated at a table within the middle of the ship staring across at other guests. When you do a sunset cruise you kind of want to be outside or at least along the glass if inside. You also might expect Hawaiian music to get you in the island spirit. Instead we had a girl who sounded like she was from Alabama playing country songs for 2.5 hours. Food was ok. Caesar salad in a small paper bowl, prime rib was cooked medium-well with a lot of gravy on top. For $150/pp recommend a dinner at Leilani’s instead. We ended up booking dinner there while on the cruise as we know it wasn’t going to be great experience.
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