Night tourCalypso Molokini Charters
South Maui: Sunset Prime Rib or Island Fish Dinner Cruise
- 4.6 (260 reviews)
- 2 hours
- Free cancellation
My pick: Prime rib or island fish, live music and two drinks: $150, two hours, 4.6 from 260 reviews.
By Rowan Ellis · Updated · Affiliate links, explained in my disclosure

A sunset cruise in Maui is the trip I would book first if I only had one evening: six boats, from $124, each two to two and a half hours, leaving from Ma’alaea Harbor, Lahaina or the beach at Ka’anapali. For the full list of cruises I compared, 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 sunset cruise in Maui is the Sail Maui sunset sailing cruise from Ma’alaea at $124: 4.9 from 142 reviews, a 54-foot catamaran, appetizers and an open bar. From Lahaina, I’d take the Alihilani from the same operator, also $124 with 4.8 from 371 reviews.
A sunset cruise in Maui, Hawaii lasts as long as the golden hour, so the start time matters more than the length. Hawaii does not change its clocks, which helps: the times below are the same every year. They are for Lahaina’s coordinates, from the sunrise-sunset.org service for the 15th of each month, in Hawaii time. They can be a few minutes off, and you can check any date on the NOAA solar calculator.
| Month | Sunset | Month | Sunset |
|---|---|---|---|
| January | 6:07 PM | July | 7:12 PM |
| February | 6:26 PM | August | 6:57 PM |
| March | 6:37 PM | September | 6:30 PM |
| April | 6:46 PM | October | 6:03 PM |
| May | 6:58 PM | November | 5:46 PM |
| June | 7:10 PM | December | 5:49 PM |
The swing is under an hour and a half through the year, so a Maui sunset cruise is a reliable evening plan in every month. The listings don’t give departure times that I can see, so look at the times offered on the booking page, and I’d board about an hour before the times above.
| Trip | Operator | Price | Duration | Boat | Rating | Cancellation |
|---|---|---|---|---|---|---|
| Sunset Sail aboard Alihilani | Sail Maui | $124 | 2.5 hours | Catamaran | 4.8 (371) | 24 hours ahead |
| Sunset Sailing Cruise from Ma’alaea | Sail Maui | $124 | 2 hours | 54-foot sailing catamaran | 4.9 (142) | 24 hours ahead |
| Luxury Sunset Cocktail Sail | Teralani | $135 | 2 hours | Catamaran | 4.7 (194) | 2 days ahead |
| Sunset Dinner Cruise aboard the Quicksilver | Quicksilver Charters | $140 | 2 hours | Double-deck catamaran | 4.5 (226) | 2 days ahead |
| 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 | $169 | 2.5 hours | Catamaran | 4.8 (164) | 2 days ahead |
A Maui sunset cruise with dinner is a different night from a cocktail sail, and three boats do it. The Calypso costs $150, lasts two hours and serves prime rib or island fish with live Hawaiian music and two drinks. The Quicksilver costs $140 for a three-course meal, two drinks and island-style music, with more drinks at $5 each. The Teralani is $169 for 2.5 hours with a buffet and an open bar.
I’d pick the Calypso for the combination of rating and food: 4.6 from 260 reviews, and the listing says the sunset glows on the Kahalawai Mountains, Lanai and Molokini. A reviewer says it was a windy night but they still saw the sunset. The listing names humpback whales from December through April, which makes winter evenings a bonus. For all three side by side, see my dinner cruise page.
Night tourCalypso Molokini Charters
My pick: Prime rib or island fish, live music and two drinks: $150, two hours, 4.6 from 260 reviews.

Quicksilver Charters
My pick: A three-course dinner cruise from Ma'alaea for $140; 4.5 from 226 reviews, parking at Maui Harbor Shops.
A sunset cruise from Ka’anapali has the best boarding in my list: Teralani guests board from the sand. Check-in is at the Aqualani Beach Activities Kiosk, along the beach walk oceanside of the Outrigger Ka’anapali Beach Resort, and exclusive parking is at the resort. There are two sails. The cocktail sail costs $135, lasts two hours and includes appetizers, an open bar and gratuities, with 4.7 from 194 reviews. The dinner sail costs $169, lasts 2.5 hours and adds a buffet, with 4.8 from 164 reviews.
I’d take the cocktail sail for a couple and the dinner sail for a celebration. Both list wheelchair users as unable to join, so check that if anyone in your group needs access. Reviewers say the crews took good care of everyone, including a family of eight.
Night tourTeralani Sailing Adventures
My pick: Beach boarding, open bar and appetizers: $135, two hours, 4.7 from 194 reviews.
Night tourTeralani Sailing Adventures
My pick: The Ka'anapali dinner version: $169, 2.5 hours, buffet and open bar, 4.8 from 164 reviews.
For a sunset cruise from Lahaina there is one boat: Sail Maui’s Alihilani. The name means the place where the horizon meets the sea, according to the listing, and the sail goes through the channel with views of Maui, Lanai and Molokai. It costs $124 for 2.5 hours and includes light appetizers, non-alcoholic drinks, and an open bar of beer, wine and cocktails. It scores 4.8 from 371 reviews, the most of any sunset trip.
You check in at the parking lot at 116 Prison St, where the crew greets you at an A-frame sign and walks you to the harbor. The only way into Front Street is Shaw Street, according to the listing, so plan the drive. People with mobility impairments are listed as excluded.
Night tourSail Maui
My pick: My Lahaina pick: $124, 2.5 hours, open bar and appetizers, 4.8 from 371 reviews.
Most of these are catamarans, but the Sail Maui Akialoa is the one I’d call a proper sailing cruise. It is a 54-foot Gold Coast catamaran that leaves Ma’alaea daily and sails the inter-island channel, with views of Maui, Lanai and Kahoolawe. It costs $124, takes two hours and has the best score of the six: 4.9 from 142 reviews. Appetizers, soft drinks, an open bar, reef-safe sunscreen and the gratuity are included. You meet at slip 72, toward the far end of the jetty side of the harbor.
Two more catamarans are not on cards here. The PWF Eco Adventures sail costs $126 and has 4.7 from only 16 reviews, and the Alii Nui happy hour sail costs $159 with 5.0 from 4. I’d wait for more reviews on both. My catamaran page compares them with the Quicksilver, and my sailing page covers the Akialoa beside two other sailing trips.
Night tourSail Maui
My pick: My overall pick: $124, 54-foot sailing catamaran, 4.9 from 142 reviews, open bar and appetizers.
The differences between the six trips are mostly in what the price covers. Every one of them includes an open bar or a set number of drinks, which is unusual enough that I’d compare the extras before the headline price. Sail Maui and the two Teralani sails include gratuities in the listing; the Quicksilver and Calypso listings are less clear about tips, so I’d carry some cash. Teralani, Sail Maui and the Alii Nui sail give you appetizers, while the Calypso, Quicksilver and Teralani dinner trips give you a full meal.
Parking is the hidden cost. The Alii Nui listing says harbor parking at Ma’alaea is about $1.06 an hour, the Quicksilver requires you to park at Maui Harbor Shops next to Maui Ocean Center, and Teralani has exclusive parking at the Outrigger. For Lahaina, the Alihilani check-in is in a lot at Prison Street. The Sail Maui and Teralani trips list a 24-hour or 2-day refund window, so you can move the date if the forecast turns, but I’d still book early in whale season, when evenings fill up.
Children and guests who do not drink are catered for too: the Alii Nui sail lists a zero-proof drinks program, and the Quicksilver and PWF trips list unlimited soda, juice and water. The Quicksilver listing excludes unaccompanied minors and smoking, so read the exclusions before you bring a family.
I’d decide in three steps. First, pick your coast: Ma’alaea for the Akialoa, Calypso and Quicksilver, Lahaina for the Alihilani, Ka’anapali for the Teralani. Second, pick dinner or no dinner. Third, check the date against the times in the table above.
If you are going in winter, my whale watching page shows the day trips for the season, and my snorkeling page shows the day alternative. Go back to the home page for the other cities. For the full set of every Maui boat trip I compared, return to my guide to boat tours in Maui.
The six sunset trips I compared cost $124 for the Sail Maui Akialoa sailing cruise and the Alihilani sail from Lahaina, $135 for the Teralani cocktail sail, $140 for the Quicksilver dinner cruise, $150 for the Calypso dinner cruise and $169 for the Teralani dinner sail. Two more catamarans cost $126 and $159.
For Lahaina's coordinates, sunset ranges from about 5:46 PM in November to about 7:12 PM in July, with local time in Hawaii not changing in summer. That is a spread of about an hour and a half, so a two-hour cruise starts mid-afternoon in winter and early evening in June. Check your date before booking.
Sail Maui's Akialoa uses slip 72 at Ma'alaea Harbor, the Calypso slips 76 to 78, the Quicksilver the Boss Frog's shop at 300 Ma'alaea Road, and Alii Nui slip 56. The Alihilani checks in at 116 Prison St in Lahaina. Teralani boards from the Aqualani kiosk on the Ka'anapali beach walk.
On most of them. Sail Maui lists an open bar with beer, wine and cocktails, Teralani an open bar on both its sails, and the Calypso two drinks with dinner. The Quicksilver includes two drinks, with more at $5 each. PWF Eco Adventures includes two premium drinks for guests 21 and over with ID.
Yes. The Calypso offers prime rib or island fish for $150, the Quicksilver a three-course meal for $140, and Teralani a buffet for $169. The other sunset sails serve appetizers. I compare the three dinner options on my dinner cruise page, with their ratings and meeting points.
The Sail Maui Akialoa sailing cruise from Ma'alaea has the best rating with a real review count: 4.9 from 142 reviews, at $124. The Alihilani sail from Lahaina has 4.8 from 371 reviews at the same price, and the Teralani dinner sail 4.8 from 164. I'd start with those three.
My full review of each one, in the order I rank them: