Inter-Island Sailing Adventure by Dan Mehrez

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Dan at Sea

Inter-Island Sailing Adventure by Dan Mehrez

At Sea

My eyes open briefly to see the sails bellow with the wind. Ever so slightly though. The boat rocks in every direction as it dances with the waves. The boom and the ropes swing back and forth on every rock of the boat, creating a smack and keeping a steady tempo with the dance. I glance up at the dark sky and gaze at the spread of stars before my eyes, and then they close again. A few minutes later my eyes open again to the same scene. The lighthouse on the island of Lana’i looks no closer.

“At this rate we’ll get there next week” I think to myself. We left Ala Wai harbor in Waikiki just eight hours ago.

Down below sleeps Captain Charley, and above deck on the bench next to me are his two granddaughters Maggie and Alex. They’re practically sleeping on top of each other to share the narrow bench. Across from them on the other bench I sit, locked in a constant struggle to keep awake. A struggle that I lose every few minutes.

Eventually, after several slow hours of sailing, Charley stirs and comes up to join me.

“Where’s the wind go to?” he asks me.

“Not here Charley.”  But sure enough, as soon as those words leave my lips the sails are pushed out and the boat begins slicing through the water. I tell Charley he must be magical.

Captain Charley

Though I don’t really think he’s magical, Charley sure is an interesting character. Born in a very small town in Missouri, he left home at 18 to join the navy and has worked as a Navy Diver for over three decades, traveling the world and even working aboard a submarine for an entire month. As I write this on October 20th, Charley is somewhere in the middle of the ocean, sailing towards Guam and then on to the Philippines. I worry a little for him. Not because I think he’ll have any trouble, but because he won’t have any eardrums to fill with constant chatter. Charley is the single most talkative person I’ve ever met. And so I briskly slip down under the deck to get some sleep before I become captured by strings of run-on sentences.

Several hours later I awake to see the island of Lana’i off the port side of the boat. Nearly the entire side of the island drops hundreds of feet to the ocean below, where the waves crash and send pillars of white foam into the air. The land above is parched and brown.

A view of Lana‘i

We soon come to a break in the cliffs where the marina can be found and we motor in to a rickety old dock. The cleats are old and loose so we tie the ropes around the entire dock to be safe. After a nice cool shower we strut over to the fancy 5-star hotel and stroll through like we own the place, sampling some fresh lemonade on the way. At the front we catch the hotel bus up to town and celebrate our secret agent skills with some lunch.

The town is tiny. There is one small grocery store, a handful of small cafes, and a bank on the corner that looks just like a house (except for the sign in the yard reading “Bank”). After taking the grand tour we head back to the boat and I wander off to the beach to watch the surfers. I sleep on the beach that night under the stars.

The next morning we have a light breakfast and depart for Maui. It’s a short three hour cruise and we soon find ourselves in the boat channel, with surfers riding waves on either side of us. We dock at the gas station temporarily and let Charley loose to find us a slip for the night. Sure enough, within a half-hour Charley comes back and announces he’s found a slip for us. Sometimes it’s useful to have a motor mouth.


That day we roam around the town, enjoy some Maui ice cream, and I go for a sunset run on the beach. I pass an older man with long grey hair and funny spectacles standing on the beach with a drink in his hand. He smiles at me and says “Good evening.” I greet him back and notice in the yard behind him a dozen more old hippies with long grey hair sipping their brews.

“Only in Maui” I think to myself.

I sleep soundly on the gently rocking boat that evening and at the first crack of dawn I hear the engine start and Charley steers us out of the harbor. I go up and watch the sun rise behind the mountains of Maui. That day we sail from dawn until midnight. The wind is at our backs for the whole sail and the seas are huge. Occasionally a large swell overtakes us and we glide down the face of the wave as though we’re surfing it. A tugboat passes us going the other direction and we watch as it fights the swells, shooting up walls of water with every wave.

Soon we see the outline of Diamond Head, then the lights of Waikiki, and finally the channel markers guiding us home. We take down the sails, motor in to our slip, and drag ourselves off the boat. As I walk down the dock I feel like I’m still aboard the boat. I probably look drunk. I thank Charley for the amazing experience, say goodbye to Alex and Maggie, and with disheveled hair and salt crusted skin, begin my stumbling swagger back home to dream of waves and winds and the open seas.