Calypso Sunset Dinner Cruises · Ma'alaea Harbor
The Calypso's evening cruise leaves Ma'alaea near sunset for two hours on the water with a plated dinner, two included drinks and live island music. It's a dinner cruise, not a snorkel trip: book it for a different day, for the view back to the West Maui Mountains and Haleakala as the light goes.
This is the same company as the Calypso snorkel trip, and the cruise leaves from slip 76 in the same harbor. You check in 30 minutes before departure, sign a waiver, and sit at shared tables on a three-level catamaran, inside or out. Dinner is served at the table: prime rib, fresh island fish, kiawe-smoked chicken, baby back ribs or penne pasta, with dessert. Your first two alcoholic drinks are included and later ones cost $5. A singer plays island music, and a photographer sells prints.
Departure follows the sun. Resellers list 5:00 PM in winter and 5:30 PM in summer; the time on your ticket is the one that counts. The cruise heads out into Ma'alaea Bay for about an hour and turns back, so expect the view and the meal, not a destination. Guests mention dolphins, rainbows and whales in season, and one September 2026 group saw the sunset but not Molokini because of the weather.
Know the downsides before you book. Seating is first come, first served, and one honeymoon couple was seated at the end of a family's table. The bay is windy in the late afternoon, so some nights you eat inside, and the critical reviews mention seasickness and uneven food. The meal you pick at booking applies to your whole party unless you call ahead. Kids under 4 get no meal of their own.
Sign the waiver at slip 76 in Ma'alaea Harbor and look over the drink menu. Seats go first come, first served.
About 5:00 PM in winter, 5:30 PM in summer; check your ticket. Drinks start as the boat clears the harbor.
Salad, your chosen main and dessert, with live music on deck.
The boat turns for home as the sun drops. Watch for dolphins, and whales from December to April.
Dock after dark. Tip the crew in cash if you liked the service.
★★★★★The sunset was beautiful, and we caught a bonus beautiful full moon rising. [...] Also, don’t eat lunch, save the room for dinner. The portions are huge. (The Prime Rib was fantastic)
★★★★★The boat had three levels and you could sit inside or outside depending on your preference. [...] There was live music at the perfect volume and they also had a photographer capturing pictures throughout the cruise.
★★★★★The crew was great, hard working and very attentive. The meal (we chose the Prime Rib) was good and cooked as requested. We saw beautiful sunsets but weren’t able to see the Molokini Crater due to the weather.
★★★★★The prime rib was so delicious. Save room for dessert (chocolate cake or cheesecake) it’s amazing also.
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It follows the sunset: about 5:00 PM from mid-October to mid-April and 5:30 PM in summer, according to resellers. Check-in is 30 minutes before. Your ticket shows the exact time.
No. It's a two-hour dinner cruise in Ma'alaea Bay. For snorkeling, book one of the morning trips, such as the Calypso to Molokini.
A plated dinner with dessert, two alcoholic drinks (then $5 each), soft drinks, juice and water, live music and tableside service. Parking, photos and tips are extra.
From about December to April, often: Ma'alaea Bay is part of the humpback whale sanctuary. Sightings aren't guaranteed. Our whale season post has the 2026-27 dates.
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A plated dinner, drinks and island music on a sunset cruise from Ma'alaea Harbor.
Molokini & Turtle Town on the CalypsoA triple-deck catamaran with slides, a glass-bottom room and two meals. Big and busy, and the easiest day for families.★ 4.6 · 5.5 hours · from $189
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