trilogy’s new aloha friday sunset sail: “sail away, sail away, sail away…”

Here in the Islands, Aloha Friday isn’t just a day on the calendar—it’s that carefree, laid-back feeling you get when the work week is all pau, and the next forty-eight hours or so are all yours. Back in 1982, musician Paul Natto even wrote a popular song about it (“It’s Aloha Friday, no work ‘til Monday…”), and hopping aboard Trilogy Excursions’ Aloha Friday Sunset Sail is just the ticket to get you in a weekend-kine state of mind.

After checking in at Trilogy’s kiosk by the Ka‘anapali Beach Hotel, my pal Joanne and I relax for a few minutes in lounge chairs on the expansive lawn near scenic Black Rock, caressed by a cool, refreshing breeze. As we await the catamaran TRILOGY IV’s return from a whale watching adventure, the chiseled peaks of Moloka‘i serve as a dramatic backdrop for the late afternoon sun’s illumination of a sparkling sapphire sea.

When deck hand Orrin announces it’s time to board, we remove our shoes and walk towards the ocean where we’ll climb a set of stairs directly from shore to boat. This afternoon an unusual west wind is causing some wave action (Captain Patrick would later tell me they refer to it as the “devil wind”), making it a bit dicey. It’s an exciting way to begin our voyage, as one by one we wait until the deck hands give the go ahead to board, and each of us gets a good soaking from the knees down in the process.

Joanne and I take seats up front along with 15 other passengers. Captain Patrick makes the introductions: crew memberes Orrin, Logan, and Kyler—barefooted, handsome young men decked out in black aloha shirts with white plumeria print—are there to serve our every need. “This is my favorite trip because we can guarantee the sun is going to set,” Patrick quips. “We’ll do it all—a little sailing, a little whale watching, a little music, and a lot of great food.”

During the safety briefing, Patrick assures us “we’ve never had to use the life jackets, and we hope not to this time.” But he goes on to say if we see him and the crew wearing one, we’ll want to get one, too! After explaining how to operate the head (“step on that foot pedal and the magic happens”), Patrick informs us no waste is discharged into the ocean, making Trilogy one hundred percent “green.”

To give us some perspective on humpback whales, Patrick explains they’re 45 to 55 feet long. “In comparison, this boat is 47 feet,” he says. Patrick enlists our help in spotting whales, but says it only counts if we shout out “thar she blows!” “Use the boat as a clock, and I’m especially interested in twelve o’clock for obvious reasons,” he says. “We don’t want to hit any whales.”

As the shoreline fades into the distance, the crew hoists the sails and we head directly into the sun towards Lana‘i. Patrick cuts the motor, and it’s immediately quiet and serene. Orrin is our musician for the afternoon, and he whips out his ‘ukulele. “The whales love ‘ukulele music, so keep your eyes on the horizon,” he says. As he performs his rendition of “Smooth Sails Ahead,” Joanne and I experience that Aloha Friday feeling washing over us. “Ah, this is the life,” we say to each other.

While we cruise along enjoying Orrin’s serenade, Logan and Kyler take drink orders: fruit juice, mai tais, red or white wine, champagne, and soda are offered. Next come plates and napkins in preparation for the pupus to come. By now TRILOGY IV is really rocking and rolling, and Joanne and I are amazed by how sure-footed the crew members are. All of us passengers wisely stay put while Logan and Kyler nimbly bring large platters of food to us—they’re completely steady on their feet as though we were still on dry land!

We happily munch on ahi poke in cucumber rings, California rolls, chicken skewers with tomato salsa and sweet Thai chili sauce, and pork spring rolls as the sun moves lower into the sky. Suddenly we hit a wave, and everyone on the port side gets a good drenching, after which the entire boat erupts in merry laughter. Joanne and I are seated smack dab in the middle so we’ve been spared!

It’s a wonderful afternoon for sailing. But where are the whales? They must be resting after having outdone themselves during the previous cruise. Captain Patrick tells me Trilogy IV was at one point earlier surrounded by the gentle giants. “I put on a mask, put my face in the water, and one of them looked right at me,” he says. “I swear he was waving at me.”

Captain Patrick has been a boatman since he was eight years old. Growing up in Venice Beach, California, he had a friend whose family belonged to the yacht club, and that’s where it all began. “The best part of my job is doing what I love,” he says. “If I weren’t working right now, I’d be playing on the water.”

Orrin performs the Bruddah Iz classic “Over the Rainbow” as the sun begins to set over Lana‘i. Partially obscured behind a group of fluffy clouds, the sun’s rays serve as a backlight while the ocean turns to cobalt. As we approach Ka‘anapali, crew members roll up the sails and Patrick waits a few moments to start the engine. We all pause to enjoy the sunset and get out our cameras for a memorable sunset photo op.
As a pink glow settles over the water and clouds gather over the West Maui Mountains, we quietly pass by Black Rock where a loincloth-clad youth is preparing for the nightly sunset ceremony. Kyler blows the pu as the young man lights tiki torches planted in the rocks. Suddenly the young man throws his lei into the ocean and follows it with a perfect swan dive. A finer chicken-skin moment than this is rare, indeed.

The moon is rising as we approach the shore, and Patrick gives instruction on how to disembark to dry land. That pesky “devil wind” is still blowing, so it promises to be no less exciting than when we boarded Trilogy IV two hours ago. Sure enough, the waves are still challenging so each of us awaits the signal from Kyler and Logan. One more good soaking later, we make our way to the beach and attempt to get our “land legs” back.

I’ve been on many a sunset cruise before, but this is one without any hype or silliness. It’s simply good fun, good company and food, stunning scenery, and plenty of Aloha Friday vibe. Driving home, I hear Paul Natto’s song in my head: “It’s Aloha Friday, no work ‘til Monday….”

–heidi pool


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