We’re asked regularly which boat has the best dinner cruise, and though some instead offer cocktails and pupus, they’re worth mentioning too. Here’s a thorough question we received and the full answer for which is the best Maui dinner cruise or sunset cruise.
“I’ve been trying to find out information on nice dinner cruises in Maui for my parents 60th wedding anniversary. Every time I think that we are settled on a cruise, I find reviews saying that they aren’t worth the $ – that there were no tables, that the drinks weren’t strong enough, or the food wasn’t as good as Mamas. I’m very frustrated as I’ve been working on this for over a month and we leave for Maui on the 19th! Do you have any advice for us?“
Thanks so much! – Andy
Thanks, Andy, for asking a really good question.
When it comes to Dinner Cruises in Maui, they’re all different. In our opinion, you’re not going to get a Michelin Star meal on any boat, but you’ll have a great time and enjoy good food (we’ve had some amazing meals on these cruises listed). The logistics are just too difficult to manage an award-winning meal. With anything, you’ll always find bad reviews. There’s always 1 guy that’s pissed off about something and thinks he’s a critic. With dinner cruises, it’s even easier to find faults. All it takes is the wind to pick up and knock over a mai tai for some schmuck to be unhappy for the rest of the trip. You have to be prepared for little things like this when on a moving boat. The good thing is that the crew is usually very good at fixing problems and making everyone comfortable and leaving happy.
Calypso
Aboard Maui’s only triple-deck catamaran, the Calypso offers a 2-hour sunset cruise departing from Maʻalaea Harbor. You’ll choose from five entrées, including prime rib and fresh fish, accompanied by a buffet of sides and two cocktails (you pay for additional cocktails.) Live island-style music is played, and you may get the addition of a whale watch experience in season!
Trilogy
Trilogy’s Captain’s Sunset Dinner Sail is a adults-only (18+) cruise departing from Maʻalaea Harbor for a 2.5-hour sail featuring a chef-prepared 4-course dinner served at intimate 2-top tables. A premium open bar complements the meal, and you’ll enjoy stargazing post-sunset.
Pacific Whale Foundation
This popular double decker Maui Dinner cruise departs daily from Maʻalaea Harbor for a 2 to 2.5-hour journey along Maui’s coastline. You’re treated to a chef-prepared 4-course dinner served at private tables, accompanied by up to three cocktails.
Kai Kanani
Departing directly from Maluaka Beach in Makena, Kai Kanani’s 65-foot luxury catamaran offers an intimate 2-hour sunset sail. You’ll enjoy a 3-course appetizer menu crafted by The Market-Maui, complemented by an open bar featuring local spirits like Ocean Vodka and Kula Rum. Live ukulele music by Dwight Quenga livens things up, culminating in a sparkling Lokelani Rosé toast at sunset.
Four Winds
While Four Winds is renowned for its snorkeling tours, it does not currently offer dedicated sunset dinner cruises. However, private charters can be arranged for sunset excursions, providing a customizable experience aboard their vessels.
Maui Custom Charters
Offering exclusive private charters, Maui Custom Charters provides 2-hour sunset sails aboard vessels like the 47’ catamaran S/V Artemis or the 42’ monohull S/V Nova. Accommodating up to 6 guests, these charters are ideal for intimate gatherings. Guests can bring their own food and beverages or arrange catering, tailoring the experience to their preferences.
No matter what you decide, it will be an unforgettable event. Everyone gets a kick out of eating on the water with the sunset and live music. We live here and we do dinner cruises every chance we get. It’s a lot of fun and perfect for a wedding anniversary.
I hope this helps, Andy. Have a great time while on island! ALOHA!
