Dinner Cruise Maui

A dinner cruise in Maui gives you a sunset, a meal and a drink on one ticket, and the three I compared run from $140 to $169 for two to two and a half hours. Two leave from Ma’alaea Harbor and one from Ka’anapali Beach. For the wider list of cruises, see my guide to boat tours in Maui. Prices are in US dollars, checked in October 2026, and booking links are affiliate links, as I explain on my about page.

My pick for a dinner cruise in Maui is the Calypso sunset dinner cruise at $150: prime rib or island fish, live music, two drinks, and 4.6 from 260 reviews. If I wanted to board from the beach, I’d take the Teralani at $169.

Dinner Cruise Maui Hawaii

A dinner cruise in Maui, Hawaii is a short evening, not a night out, so pick the one whose food you want. The table puts them side by side.

Trip	Operator	Price	Duration	Boat	Rating	Cancellation
Sunset Dinner Cruise aboard the Quicksilver	Quicksilver Charters	$140	2 hours	Double-deck catamaran	4.5 (226)	2 days ahead
Sunset Prime Rib or Island Fish Dinner Cruise	Calypso Molokini Charters	$150	2 hours	Catamaran	4.6 (260)	2 days ahead
Luxury Sunset Dinner Sail	Teralani Sailing Adventures	$169	2.5 hours	Luxury catamaran	4.8 (164)	2 days ahead

The Calypso is the one with the most to say for itself. The listing describes a sunset glowing on the Kahalawai Mountains, Lanai and Molokini Crater, a gourmet dinner, two drinks from the bar and Hawaiian music, with a complimentary drink after the boat leaves the harbor. It meets at Ma’alaea Harbor, Slip 76 to 78. A reviewer says the night was windy but they still saw the sunset, and the food and entertainment were good. The listing names humpback whales from December through April.

Night tour

Calypso Molokini Charters

South Maui: Sunset Prime Rib or Island Fish Dinner Cruise

• ★ 4.6 (260 reviews)
• 2 hours
• Free cancellation

My pick: My pick: prime rib or island fish with live music and two drinks, $150, 4.6 from 260 reviews.

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$150

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Cocktail Cruise Maui

If you want drinks without a full meal, a cocktail cruise in Maui is a better fit, and I have one on the list. The Teralani luxury sunset cocktail sail costs $135 for two hours, with appetizers, an open bar and gratuities, and 4.7 from 194 reviews. That is $34 less than the Teralani dinner sail and a half hour shorter. It boards from the same Ka’anapali kiosk.

Alii Nui’s luxury catamaran happy hour sail is another cocktail option, at $159 for two hours from slip 56 at Ma’alaea Harbor. The listing mentions a premium open bar with craft cocktails, local spirits and Maui Brewing beers, plus a zero-proof menu of non-alcoholic spirits, wine and beer. It has a 5.0 rating, but from only 4 reviews, so I’d not call it a favorite yet. Both are on my sunset cruise page.

Maui Cocktail Cruise

On a Maui cocktail cruise the drinks are the main event, so check what each listing says. The Teralani lists an open bar and appetizers. The Quicksilver dinner cruise lists two alcoholic drinks, with more at $5 each, plus unlimited soda, juice and water. The Calypso lists two drinks, and a complimentary drink as the boat exits the harbor. Anyone who wants to drink more should pick the Teralani, whose open bar is the only one without a drink cap on a dinner trip.

The Quicksilver listing excludes smoking and vaping, children aged 0 to 3 have no meal included, and unaccompanied minors are not allowed. Those are the points I’d check if you bring a family.

Quicksilver Charters

From Ma'alaea: Sunset Dinner Cruise Aboard the Quicksilver

• ★ 4.5 (226 reviews)
• 2 hours
• Free cancellation

My pick: The cheapest dinner cruise: $140, three courses and two drinks, 4.5 from 226 reviews.

from

$140

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Dinner Cruise Maui Kaanapali

The Ka’anapali dinner cruise is the Teralani sunset dinner sail, and it is the best-rated dinner trip in my list: 4.8 from 164 reviews. It costs $169 for 2.5 hours and includes a buffet-style menu and an open bar, and gratuities are listed as included. You board from the beach: check in at the Aqualani Beach Activities Kiosk along the Ka’anapali beach walk, oceanside of the Outrigger Ka’anapali Beach Resort, where exclusive parking is available.

The listing describes oceanfront views from every seat and a state-of-the-art catamaran for special occasions. Reviewers say the crew went out of their way to make the afternoon memorable. Wheelchair users are listed as unable to take it. Cancel up to 2 days ahead for a refund.

Night tour

Teralani Sailing Adventures

Ka'anapali Luxury Sunset Dinner Sail

• ★ 4.8 (164 reviews)
• 2.5 hours
• Free cancellation

My pick: The top-rated dinner trip: $169, 2.5 hours, buffet and open bar, 4.8 from 164 reviews, boards from the beach.

from

$169

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Maui Dinner Cruise Kaanapali

A Maui dinner cruise in Ka’anapali is the one with the least travel if you are staying on the west side. From Ma’alaea Harbor to Ka’anapali Beach it is about 14.7 miles in a straight line by my calculation, and the road is longer, so a south-side stay should choose a Ma’alaea trip. Lahaina Harbor and Ka’anapali Beach are only about 3.4 miles apart.

That distance is the practical reason to pick by coast: the two Ma’alaea dinner cruises suit Kihei and Wailea, and the Ka’anapali sail suits Lahaina, Ka’anapali and Kapalua. I’d also leave time for traffic on the way, because the listings give no departure times, and sunset in winter comes before 6 PM according to the sunrise-sunset.org service for Lahaina’s coordinates.

Dinner Cruise Maui Kihei

A dinner cruise from Kihei isn’t in my data: all three leave from Ma’alaea or Ka’anapali. Kihei Boat Landing is about 7 miles from Ma’alaea in a straight line, which gives you an idea of the drive from a Kihei hotel. The Calypso and Quicksilver both depart from Ma’alaea, so they are the closest dinner cruises to Kihei.

Parking at Ma’alaea is the thing to plan. The Quicksilver listing says passengers must park at Maui Harbor Shops, next to Maui Ocean Center, at 300 Ma’alaea Road. The Calypso listing doesn’t say where to park, so ask the operator when you book if you are driving.

What a Maui Dinner Cruise Costs Per Person

The ticket prices look close, but the extras are different, so here is how I compare a dinner cruise in Maui. The Quicksilver is $140 for two hours, which is $70 an hour. The Calypso is $150 for two hours, $75 an hour. The Teralani is $169 for 2.5 hours, about $68 an hour, which makes it the best value per hour despite the highest sticker price. On top of that come the drinks: the Teralani’s open bar has no cap, the Calypso gives two drinks, and the Quicksilver gives two with extras at $5 each.

Seasickness is worth a line. The Calypso listing excludes people prone to seasickness, and the Quicksilver’s double-deck design lets you choose between the upper deck and the cabin below, so a seat in the cabin is the quiet option if the water is rough. None of the listings states sea conditions, and I won’t guess them. A dinner cruise in Maui is a calm evening more often than not, but the Calypso review of a very windy night shows it is not guaranteed.

Finally, think about timing. A winter dinner cruise starts in daylight and finishes in the dark, because sunset is before 6 PM in November and December, while a summer one runs on past 7 PM. That changes how hungry you will be when the food arrives, so ask what time boarding is on your date.

How to Choose

I’d decide by the coast and the menu. South side, I’d take the Calypso for the music and the rating, or the Quicksilver to save $10. West side, the Teralani. Compare it to the sunset-only sails on my sunset cruise page, and read my sailing page and catamaran page for the boats. In whale season, my whale watching page and the snorkeling page show the daytime trips. The home page lists other cities. For every Maui boat trip I compared, return to my guide to boat tours in Maui.