Beyond The Beach: Sailing to Lanai with Trilogy

Relaxing in Maui is easy, but I wanted more than just days at the beach. To me, the sea isn’t just a beautiful backdrop; it’s a playground. I was after aquatic adventure, and I got it with a day trip to Lanai on the Discover Lanai catamaran tour offered by Trilogy Excursions.

It began with an enjoyable walk to Lahaina harbour. There, I joined my fellow sailors. They were a mix of families, younger and older couples, plus another single traveler. The families with children took the hammock on the front of the boat (called, for good reason, the splash zone); I grabbed the nearest table. Over coffee, passengers who’d been on this excursion before filled me in on their experiences in Maui. (It says good things about the Trilogy experience that so many who’ve had it want to repeat it.)

With everyone aboard, Captain Brian introduced us to our crew and fellow passengers, and sketched out the day ahead. Lanai lay on the horizon, nine miles away. The morning calm offered no wind for our sails, so we motored out of the harbour.

As the sun rose, we skimmed across the ocean, noshing on big, gooey, cinnamon buns, taking deep, appreciative sniffs of the salt tang and keeping eager eyes out for whales. Humpback watching season starts in mid December with the arrival of an advance guard of males (the females make their way here later.)

Soon, we spotted a whale in the distance. As we headed towards it, it dove deep, the massive tail slipping smoothly into the water. Shortly afterwards, we spotted a second humpback. It’s an incomparable experience to watch these magnificent mammals in the unbounded blue of their natural habitat.

Maui Sailing

A humpback whale off in the distance




As we enjoyed snack wraps and drinks, the steep sea cliffs of Lanai hove into view.  From their tops to where they plunged into the sea a hundred feet below, they show a rough, weathered beauty.

After docking, we travelled to Hulopo‘e Beach Park. The park’s protected status as a marine reserve keeps the reef here exceptionally healthy, with clear water and a wide variety of fish. That’s made it, literally, an award-winning place to snorkel. And Trilogy is the only tour company with permission to take snorkelers to Hulopo’e Bay, ensuring an uncrowded experience. (Out of consideration for the locals, they don’t run this tour on weekends or holidays.)

The warm, sandy beach and calm seas made me keen to hit the water. Trilogy requires their guests to wear flotation devices while snorkeling, and offers a choice of  two types. The lower-profile one allows more experienced snorkelers to free dive, while the “floatier” model lets newbies or those after a more relaxing experience bob effortlessly on the surface. Since I hadn’t snorkeled or swum in a while, I opted for the surface model first. I stroked lazily out, then simply drifted, watching schools of colourful fish dart and weave below me. Later, I changed into a dive-type floatation device so I could get down and visit with my finny new friends.


Not long after, I took time to check out the land-based attractions in the area. Following the walking path, I explored the tide pools before heading to Puu Pehe, better known as Sweetheart Rock. Local legend recounts how a young warrior from Lanai captured a young princess from Maui and brought her back to be his wife.  Because he was afraid to allow other men to be exposed to her beauty, he confined her to a sea cave near the rock. One day while he was away, the weather suddenly changed for the worse and drowned the captive princess. Heartbroken, the warrior climbed the steep cliffs of the island and buried her in a tomb, then leapt off the cliff to his death. The story is especially haunting to recall when you’re standing where it’s set, watching the powerful surf pound unceasingly against the shore.

Next, I made my way back to take the optional van tour of the island. It really filled in the gaps of my limited knowledge of Hawaii. Lanai is the sixth-largest of the Hawaiian Islands, but only about 3,200 people live here. Previously known as the “Pineapple Island”, it once was home to a plantation that produced 75% of the world’s pineapples. The plantation shut down 1992, unable to compete with overseas rivals and their cheaper labour.

In 2012, Oracle entrepreneur Larry Ellison purchased 97% of Lanai for 300 million dollars. Along with the new owner came many questions about the island’s future. Lanai has two Four Seasons resorts, both currently under renovation, plus a small hotel and various B & Bs. The locals are eager for the resorts to re-open as tourism is a major employer here. Our guide was a good example: a local herself, she shared stories from her family’s generations of experience as she drove us around her town. I want to return to Lanai: any island with no traffic lights is clearly a peaceful place. And there’s plenty of off-road exploring to do.

Hulopo‘e Beach Beyond The Beach: Sailing to Lanai with Trilogy//

Lanai Sweetheart Rock//

Beyond The Beach: Sailing to Lanai with Trilogy//

Beyond The Beach: Sailing to Lanai with Trilogy//

Back at the harbour, we were treated to a Kiawe wood BBQ dinner, served at the Hale O Manele Bay, which overlooks its beautiful namesake inlet. We feasted on Stir Fry Hawker’s Noodles, pineapple glaze chicken, BBQ corn, and salad. The recipes are posted on Trilogy blog, so you can recreate the taste, if not the ambience, of this tropical paradise (Unless you’ve been here, in which case the scents and flavours can transport you back, at least in your mind.)

For the voyage home, I sat on the webbing net at the front of the boat, where I could look directly down to where blue water rushed between the twin hulls. A choppy sea gave the ride the exhilarating feel of a small roller coaster, with the boat surging up each wave and dropping down into the troughs! As a bonus, we were able raise the sail up for part of the journey back. We coasted along enjoying drinks. I opted for Moloka‘i Mule and Lana‘i Tai, but wine and beer were also on offer. Since you shouldn’t drink on an empty stomach, we simply had to partake of the delicious ice cream with fudge the crew were serving.

Beyond The Beach: Sailing to Lanai with Trilogy//

Trilogy Drinks//

Beyond The Beach: Sailing to Lanai with Trilogy//

Approaching the harbour, we lingered over the last moments of our day by stopping to enjoy the sunset over Lanai. As I said goodbye to the crew, I couldn’t thank them enough for how well fed and happy they kept us during the trip. I’ve been lucky enough to experience some great outings on my travels, so I have a good basis of comparison when I say this company really stands out. They go above and beyond to make the experience memorable and special, from teaching guests how to snorkel to helping children find an octopus, and making us laugh throughout the day. I can’t wait to return to Maui and sail with them again.

Have you gone sailing in Hawaii or do you want to? I would love to hear about it below!

Beyond The Beach: Sailing to Lanai with Trilogy//

Beyond The Beach: Sailing to Lanai with Trilogy

If you want to read more about Hawaii, check out Recovering in Hawaii.

4 thoughts on “Beyond The Beach: Sailing to Lanai with Trilogy

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