trilogy captain’s sunset dinner sail: fine dining with an unbeatable view

TRILOGY_CSDS High Res-6727What could be finer than dining right next to the ocean at sunset? Give up? How about feasting on an elegant multi-course meal aboard a luxury sailing catamaran hosted by a genial captain and his crew? Now that’s what I’m talking about! Trilogy’s Captain’s Sunset Dinner Sail is the bomb.

There are strong on-shore winds in the late afternoon when Susan and I board Trilogy II at Ma‘alaea Harbor, so we’re not sure what to expect once we get out on the water. The catamaran’s brilliant white deck and cabin are complemented by navy blue and white striped fabric on the cushioned benches. Cozy tables for two have been set with white plates and blue napkins. Crew members are color-coordinated as well, looking snazzy in crisp white shirts with navy-blue shorts.

Susan notices a table is available up on the boat’s bridge right next to the captain, so we snag it. Captain Martin Kirk hails from North Carolina, and says he’s been a sailor his entire life. But being a captain for Trilogy the past eight years is the icing on the cake. “I never thought in a million years I’d actually get paid to sail!” he marvels.

Captain Martin descends from the bridge to welcome everyone on board, and introduce crew members Alex, Kama, and Max. “There’s just enough wind this evening to do a light sail, but not enough to mess up your hair,” he tells us. “And, for an added bonus, we should see plenty of whales. Don’t be embarrassed to point them out—feel free to jump up and down when you see them.”

Our chef this evening is Marcus Antonius from Maui Flavors Catering, which is owned by Chef Will Bailey (a.k.a. “Bruddah Willy” of Bruddah Willy’s Sticky Ribs fame). Marcus tells me he’s been a chef for the past 30 years. “Serving a four-course dinner on a boat outside the second windiest harbor in the world [Wellington Harbour in New Zealand holds the distinction of being #1] has its challenges, but no matter what, we always have a good time and leave happy,” he says.

Crew member Max brings Susan a glass of Champagne, while I opt for a Moloka‘i Mule (vodka, lemon elixir, ginger, lime, and cane sugar). Alex brings yummy freshly baked breadsticks dusted with Hawaiian sea salt and served with liliko‘i butter. Surprisingly, the ocean is fairly calm and, as sunset approaches, it turns a deep cobalt blue.

Captain Martin tells us Trilogy II is the newest vessel in the fleet. Built in 2010 by Schooner Creek Boat Works in Portland, Oregon, it’s 64 feet long, and boasts 1,950 square feet of working sails. “Eight of us traveled to the Mainland to collect the boat and sail it to Maui,” he says. “We were at sea for 17 days.”

Speaking of working sails, Captain Martin determines it’s time to allow Trilogy II to do what it does best. He turns the boat around, pointing it straight into the wind, while crew members hoist the main sail with what appear to be carefully choreographed movements resembling those of synchronized swimmers. Kama winches out the jib, the captain cuts the engines, and we’re under full sail power. On the port side of the boat, the sinking sun illuminates a shimmering ocean pathway directly to the neighboring island of Lana‘i, and one of the passengers points out a pod of cavorting humpback whales. To the starboard side, the pali is in full green splendor from recent rains. With the boat gently undulating, you can’t help but be lulled into a relaxed state!

Back to the business of dinner, our crew members serve us a trio of tasty bites to whet our appetites: juicy cucumber slices topped with Maui onion cream cheese; crusty triangles of pita bread layered with smoked salmon, capers, onions, and fresh dill; and tataki-style beef tenderloin served with crisp lettuce and caramelized Maui onions atop crunchy crostini.

Captain Martin points out the “wind line” on the ocean near the pali. “We’re going to head over there so you can enjoy your dinner,” he says. Meanwhile, Kama has everyone in stitches taking photos of each pair of guests with a plastic toy whale he calls “Bob”—in the resulting image it appears as though a gigantic whale is breaching in the water right next to you! Susan and I take our turn, making the appropriate expressions and gestures of surprise and wonder as instructed by Kama. Our photo is definitely a keeper, and I have fun for the next several days fooling unsuspecting friends.

As promised by our captain, the wind drops off, and we motor to a calm cove as the muted yellow sun begins its descent behind Lana‘i. Alex serves us generous helpings of Trilogy’s signature Caesar salad: tasty lettuce with just the right amount of dressing is garnished with parmesan cheese and fresh peppery watercress.

Captain Martin announces it’s time for “whale karaoke,” and Kama plunges a hydrophone into the ocean. Male humpback whales emit a series of repetitious sounds at varying frequencies known as whale songs. Marine biologists say the songs are among the most complex in the entire animal kingdom. Whale songs are eerie, yet beautiful.

As darkness approaches, Kama presses the “magic button,” and the candles gracing each table illuminate right on cue. As we feast on pan-seared rosemary and garlic crusted steak, and wild-caught mahi mahi topped with lemon-butter caper sauce (a vegetarian pasta option is available for non-meat-eaters), both accompanied by creamy roasted garlic mashed potatoes and sautéed vegetables, the sky at the horizon turns pink and the full moon dances in and out of cottony gray clouds. On shore, is another sea of sorts—this one consists of twinkling lights. Suddenly, the moon emerges fully, glowing like a diamond in the night sky, creating a magical glittering effect on the ocean.

Max brings our dessert: a luscious threesome composed of liliko‘i cheesecake garnished with a juicy blackberry; a decadent dark chocolate truffle; and a magnificent fresh strawberry sliced like flower petals; all presented on a schmear of strawberry sauce. With reggae music playing in the background, and our minds and bodies in full relaxation mode, Susan and I think this has been one fine way to spend the evening.

Family-owned Trilogy Excursions takes seriously the responsibility of supporting the local Maui community, and has a strong commitment to preserving our ocean and island environment. A portion of ticket prices goes to Trilogy’s Blue ‘Aina Reef Cleanup Program, maintaining day-use mooring (which also helps to save our reefs), assisting the Whale Sanctuary & NOAA, and eliminating overboard discharge. Trilogy is the first company in Hawai‘i to retrofit its boats to pump all waste onshore.

–heidi pool



Trilogy Excursions’ Captain’s Sunset Dinner Sail: fine dining with an unbeatable view aboard a luxury sailing catamaran. Cost is $129 per person.


Departs from slip #62 at Ma‘alaea Harbor. Parking is free.


Offered Monday, Wednesday, and Friday at 5:15 p.m. The dinner sail lasts for 2.5 hours. Guests must be at least 21 years of age.


Reservations essential: 888-225-MAUI (6284);

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