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Tour Highlights:
  • CLOSED due to COVID-19 pandemic (30-days from March 19- April 17).
  • The Calypso doubles as both a sunset cocktail cruise and a dinner cruise boat on the same trip.
  • A portion of the large boat is for those choosing dinner and another portion is for those simply choosing the cocktail cruise.
  • Departs from Maalaea Harbor.  
  • 80' 3 deck power catamaran with table seating, 3 restrooms and is ADA accessible.
  • 2.5 hours
  • Maximum of 120 passengers.
  • 2 complementary adult drinks included (beer and Ma'i Ta'is).  2 additional are available at an extra cost.
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Activity Rates Your Price (Before taxes/fees)
$ 49.95
$ 24.95

Today's Prices are shown. To request a reservation please select a Day and Time from the calendar below.
Hawaii State sales tax is 4.167%. The cost of additional fees required to be applied by the tour company (if any) can be seen by proceeding to the Activity Cart Order page.

Calypso Sunset Cruise is a two and a half hour sunset sightseeing adventure aboard the Calypso Dinner cruise along the Maui coast! This tour is a great option for families who want to enjoy the sunset on the ocean with drinks only. Guests 21 and over will have two complimentary adult drinks with additional drinks available for purchase. The Bar offers: Mai Tais, Beer options and blended drink favorites like Pina Colada and Lava Flows. The calm ride on this catamaran cruise provides the perfect way to end a perfect Maui day.
For our guests needing assistance with a wheelchair or walker please inform vendor at time of reservation so that you can be properly accommodated.
Operates: Monday, Wednesday, Friday and Sunday with with a check-in between 4:00 pm or 5:30 pm and departures half hour later. Times vary seasonally when placing reservation agent will confirm time for date being booked.
Departure Point: Maalaea Harbor, Slip 82 - Main Loading Dock. 101 Maalaea Boat Harbor Rd Wailuku, HI 96793
Duration: 2.5 hours.
Equipment: Calypso is a new 80 foot power catamaran with three separate decks with table seating. Three restrooms, including an ADA accessible one.
Capacity: Up to 120 passengers.

Water and an assortment of non alcoholic beverages.Guests 21 and Up
Two complimentary adult beverages of beer or MaiTai's are included.
Please bring a valid picture ID to be served alcoholic beverages.

Inclusions: Guide, sunset cruise with live entertainment, two complimentary adult drinks with a possibility of seeing whales during winter season.
Exclusions: Two additional alcoholic beverages are available for extra cost.
Restrictions: *SPECIAL 2 for 1, price of $24.95 is for ONE person, MUST reserve for 2 to equal the $49.95 Special. This tour has a 48 hour cancellation policy. This means that once you're within 48 hours of the start time, the tour is non refundable. If you choose to cancel before this time, the standard 3% cancellation fee will apply. If the vendor needs to cancel your tour because of weather, a mechanical issue or any other reason you will receive a 100% refund of the price you paid.

ADA Restrictions:
Wheelchairs and Walkers are available but vendor restrictions will need to be confirmed on a case by case basis. Often wheelchairs need to be left behind and guests must be able to maneuver transfers to the aircraft. Guests will be advised if they must have others in their party to assist them in order to participate. Agent will assist you at the time of booking.
Pride of America Cruise Ship: For Pride of America Cruise Ship passengers tour company will not pick up cruise ship passengers at the cruise ship dock. This tour can be reached via a taxi or Tom Barefoot's Tours could arrange for a rental car shuttle to pick you up directly at the dock. This tour can be organized for Sunday of your cruise ship schedule.

There have been 7 reviews written about the with .

Average Product Rating: 4.9 / 5

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Jim Marker
This was the absolute high light of our trip to Hawaii! Fortunately we saw several pods of whales and spinner dolphins as well and if that wasn't enough, we saw the full moon come up over Halakela! Add it all up and it left us delighted!!!

Cindy McMeekin
The crew aboard were all very attentive and friendly. I was under the impression that there would be pupus, however, it was only drinks. I guess that was my mistake. It would have been nice though.
The trip itself, was rather miserable. It was due to an extremely windy evening and had nothing to do with the captain...He did his best.
I would definitely book again but I will make sure to eat prior to the trip!

Michael Sawyer
This sunset cruise was fantastic! The crew were extremely friendly and helpful. The drinks were great. They had the best mai tais I had in Hawaii. And the cruise was wonderful, it was 2 hours long and there were many great views.

Amy Oh
We loved this cruise! The boat was almost a size gorgeous as the views!! The only recommendation Id suggest is for the cocktail cruise, there is no food, when we booked it said there would be potstickers and veggies, so Im the only one who didnt eat thinking that would hit the spot. I just think that needs to be made clear. The cruise is just lovely and the music was great! The captain was entertaining and the crew were very attentive! We loved it!

Alan Gamble
We went on the Calypso August 19th. It was so windy at Maalaea harbor that you
could barely stand up. I wondered if they would cancel the cruise. But when we
got out on the water I could not believe how smooth the boat was. We sat on the
very front of the boat, it was smooth and the views along west Maui were
beautiful. The crew was very friendly and helpful, and the restrooms were the
cleanest of any boat I’ve ever been on. Overall, it was a 10 out of 10

Jeff Moody
Great way to spend some time on the water in Hawaii.  Highly recommended.
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Leontine Clark
It was a great experience. The crew was very friendly and knowledgeable. I would
recommend anyone coming to maui to do this tour

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