Trilogy Sunset Dinner Sail Review
We had a wonderful time and cannot wait to enjoy another sunset dinner sail.
Meal Quality 93%
Service 98%
95%Overall Score
Reader Rating: (22 Votes)

When it comes to things I enjoy, boat rides on the ocean are generally toward the top of the list. Add in whale watching during sunset, an open bar, a three-course dinner, and a random assortment of Hawaiian and 80s tunes, and it’s essentially a perfect storm of awesomeness.

Last month I hopped on Trilogy’s Sunset Dinner Sail, which departs weekly from Maalaea Harbor on Mondays, Wednesdays, and Fridays. We were promptly greeted by a few friendly staff members and escorted to our seats, a maneuverable and lovely table for two on the port side of the sailing catamaran (look at me using my boat words!).

After a short ‘boat safety’ and welcome spiel, we sailed out of the harbor and were given permission to take advantage of the premium open bar, which consisted of a Moloka’i Mule, Lana’i Tai, local beer from Maui Brew Co., Longboard, Bud Light, Champagne, and Wine. Game on. Servers rotated around with an assortment of pupus, including beef tenderloin crostinis, bread with lilikoi butter, cucumber with cream cheese, and salmon pita bites. Yum!

maalaea harbor dinner cruise

While the day had been windy, as soon as we got out on the water, the wind calmed down, allowing for a relaxing and calm-weathered cruise that did not require constant removal of hair from around my face. Almost immediately after leaving the harbor, we spotted several whales in the distance, coming up for air and pec slapping not far from the boat. One particularly frisky fella (or lady) even breached right in front of the boat.

maui cocktail cruises

Soon enough, dinner began. We started with a yummy caesar salad before moving onto our pre-chosen steak entrees (they also have a fish and vegetarian option), accompanied with mashed potatoes and mixed vegetables. Considering this meal was prepared on a boat, I was really impressed with the level of detail they put into the experience. From the sexy candle on the table (of the battery sort, obviously), to the convenient drink cup-holders and plating presentation, not to mention the sincerely friendly service, it’s definitely on par with any nice restaurant you’d go to back on land. Only better, because it’s on a boat. Duh.

sunset cruises maui

trilogy excursions dinner cruiseThe sunset was unshockingly beautiful, as they tend to be on remote tropical islands, and as we watched the last of the evening’s humpback whales wish us a lovely evening farewell, dessert was served. A combination of lilikoi cheesecake, chocolate truffles, and fresh fruit, we finished the last of our excellent cocktails (get the Moloka’i Mule) before heading back to shore.

I’ve been on several boat tours on Maui, and Trilogy’s table service was a nice touch, compared to the typical buffet-style found on most others. Our table neighbors had actually been on a kayak tour with my boyfriend the day before, and by his recommendation, decided to whale watch from a boat as well.

cocktail cruises maui

One last note that’s particularly awesome is the fact that a portion of all ticket sales go to their monthly Blue ‘Aina Reef Cleanup project, which I’ve participated in previously and enjoyed. It’s always good to give back on Maui.

sail trilogy dinner cruise

Big mahalo to Trilogy for an excellent evening on the ocean. I’ll definitely be back!

Sunset dinner sail tours last approximately 2.5 hours, cost $129 per person, and are only open to guests 21 and over.

7 Responses

    • Jackie

      Aloha, Booked sunset dinner cruise with Trilogy . However, as we sat at Kimo’s in Lahaina tonight at sunset , we Saw many catamarans pull out under power from Lahaina Harbor then anchor just in front of Kimos. Didn’t see any actually sail , much less move from anchorage just off shore from Front Street. Is this what to expect from “Dinner Cruise” ?. Actual cruise about 1/2 mile offshore? Please share any info you have on subject. Mahalo

      • Maui Guide

        That’s a good question. I personally do a dinner cruise at least 4-5 times a year, being a full-time Maui resident. That says quite a lot right there. If there’s enough wind, and conditions are good, you’ll sail. If not, you’ll motor and coast. Regardless of the sail, dinner cruises are awesome! Personally, I believe it’s the best on the water dining experience. There’s something special about eating out on the ocean where your view from the table constantly changes. Most boats cruise around so you get good views of different coastline. That being said, sunset dinner at a Front Street restaurant is great too.

  1. Dale Perry

    My wife and I booked with Trilogy in 1998. It was our first time in Maui and it was a very special experience .We sailed to Lanai and were very impressed with the crew.And the over all professionalism of all . The crew knew our names before we got out of the harbor and treated us like long lost friends (the good kind ! ). My wife and I
    have been back to Maui every year since, several times, twice a year,and still rate the
    Trilogy trips as number one . Maui no ka oi !

  2. Dardanela Reeves

    Can I make a reservation for group of 4 on May 28 it’s my anniversary thank you

  3. Keith

    Is this the dinner cruise catamaran that passes Kimo’s on the way back to Maalaea Harbor with white lights up and down the sails?


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