Originally published on October 6, 2020 in Endless Summer State of Mind

One of my sincere hopes in moving to the Caribbean was to dedicate far less time to work and far more time to fulfilling my passions. (It hadn’t quite dawned on me yet that I might be able to combine the two.) In addition to my land-based joys, like music and photography, I was also looking forward to time in the water. Two years before my move I had traveled to Hawaii where I went snorkeling for the first time. I swam with my first sea turtle in Hanauma Bay and fell madly in love. I couldn’t wait to get as much time under the crystal clear St. John water as possible. It should come as no surprise to my fellow sea turtle fans that Maho quickly became my favorite beach on the island.

What I had not anticipated was the fact that I would also fall in love with being on top of the water. It was almost a year after my arrival before I sailed for the first time, and then I had two experiences in one month that hooked me for life. We were celebrating Kellie’s birthday with a boat trip aboard Kekoa. When I watched those black sails go up on the 50ft catamaran it was something to behold, but the real magic happened the moment the engine shut off. I adored the quiet that came with being UNDER the water, but I had never experienced being ON the water with that kind of peace. I loved power boats with their speed – the race, the thrill – but this, THIS seemed like the way you were MEANT to be on the water. It felt like a relationship with the ocean that fit in perfectly with the natural order of things. It was that same pace that I was learning to embrace in my new life – slow, in tune with the elements, enjoying the journey rather than focusing on the destination. It felt like something that I definitely wanted more of.

A month later, I was invited to join my friends Grace and Sunny for the sailing excursion that would solidify that desire for good. We went out on Grace’s 32ft. monohull Alcyone for an overnight trip to the Hans Lollik Islands, north of St. Thomas. I was surprised at the difference in the movement of the boat from that of the large catamaran. I loved being that close to the water, knowing if the boat heeled over far enough that you could reach out and graze the ocean with your fingers tips. It felt sort of scary and reassuring all at the same time. The sail there was smooth. We arrived in about 2 hours and anchored at the base of the channel between Little and Big Hans Lollik. We lounged onboard for a bit and then went for an amazing snorkel. It was my first time swimming with a school of tarpin – they were easily my size. It felt like a legit “mermaid moment”. We took the dinghy to the perfect spot for sunset and kept our eyes out for the green flash. Then it was back to the boat for dinner and guitar time. It felt like I had stepped into another world. Cooking dinner and playing music ON A BOAT, ON THE OCEAN– it seemed like something out of a movie. It felt like someone else’s life.

The next morning we were up and at it early because Sunny needed to be back for a work shift that afternoon. The expectation was another nice and easy sail back with plenty of time to spare. And then two things changed – the weather shifted and the engine died, almost simultaneously. To top it off, the engine died in the worst possible of locations and the shift in wind had us drifting towards rocks. Grace and Sunny were both experienced sailors and they didn’t miss a beat. I watched in awe as they both jumped into action. They had the sails up and the boat moving to safety in what seemed like the blink of an eye. The wind picked up again and extra hands were required. Grace threw me a line. I told her that I had no idea what to do and she said that I only needed to follow her instructions. “When I say ‘pull this in,’ pull it in. When I say,’ let it out,’ let it out.” And so it went. The change in circumstances also required charting a different course back to Cruz Bay, which meant tacking on a lot of extra distance and time. All in all, it was a wild ride.

“Went sailing and man was it a sailing trip. We lost our engine in 18kt winds. 4 mi. trip turned into 20mi, the hard way. It was awesome!”

Sunny's Facebook status that night

When we finally found ourselves safely on a mooring ball in Cruz Bay, Grace looked at me and she said, “Girl, that was no joke and you had a smile on your face the ENTIRE time. You are a sailor!” I could feel that smile broaden further and I knew that she was right.

Just as my move to St. John unfolded in a serendipitous fashion, so too did my journey to sailing. Once the desire was full blown, the rest began falling into place immediately. The day after our Hans Lollik adventure, I had a new roommate move in. I truthfully, don’t even remember how Ben and I got connected other than the memory that I was in need of a new roommate ASAP and he came with trusted recommendations and a rent check in hand. It turned out that Ben was captaining for a sailing charter and would be happy to teach me to sail if I wanted to come along as crew. Some unforeseen circumstances caused Ben to leave island about a month later, but it was enough time for the ball to start rolling, a friendship to be forged, and me to be forever grateful.

Just as Ben was realizing that he would have to head out, I started classes to become scuba certified. It turned out that my instructor, Jason, worked for the same sailing charter! He captained the second boat. When he heard that I was crewing with Ben, he told me that he would also be happy to teach me the ropes. I spent the entire next season crewing for Jason. It was a blast! My favorite trips were the sunset sails. After a while I started bringing a guitar along and would play for the guests after we served drinks and set out the cheese plate.

Despite my strong desire to be on the water, my lack of confidence at the time caused me to stick to learning how to crew more so than learning how to sail. I could tie lines, drop anchors, raise sails, pour rum punch, and cut a beautiful fruit tray. I was, however, too timid to get comfortable at the helm. But fate had plans for me and they would lead to an adventure that would change my life in ways that I could not yet imagine. As it turned out, only a week after my trip with Sunny and Grace, I met someone at my very first gig on island. He was a musician and a sailor and he was passing through for a few days while he repaired his boat engine before continuing his travels down island. Two years later he would invite me to spend a couple of months singing and sailing our way through the Caribbean…and so would begin the epic story of the “Boys On The Boat” (which I will tell you all about in next month’s issue. Stayed tuned!)

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