Cruising with Holli: The First 4 Years

My name is Holli and I live on a boat. Today marks one month shy of four years we’ve lived aboard Shiloh. That we’ve been cruising. That we’ve been sailors.

I can’t quite believe it, to be honest. I still feel like a newbie, an observer. But at the same time, I can’t imagine living on land.

Sailing is another adventure in a life of many. I’m from suburban Canada, and my hubby is from Cape Town, South Africa. We met in Ghana, West Africa 15 years ago, working in the telecoms industry. We were instant soul mates with restless souls. We very quickly concocted a plan to escape our jobs and our then-current lives. The first idea was to fit out a camper van and drive from Cairo to Cape Town, but with the crime and border issues we’d experienced working across the continent, we decided it was too dangerous and that perhaps sailing the world would be a better idea. Only I’d never been on a boat in my life. In fact, the day we took ownership of Shiloh five years later, was my very first time. No lessons, no starting with a small boat; we just jumped right in.

Shiloh is a 41-foot French built Lagoon catamaran with four cabins and four heads. She was built for chartering and that’s what she did for a few more years, while we worked to save some money and fully plan our escape. With our last child off to university in 2012, we moved aboard and never looked back.

We ticked many bucket list items over the past four years of sailing the eastern Caribbean, the Bahamas, and the east coast of the USA. We’ve sailed right up to the statue of liberty, which was amazing and gave me tingles all over. We’ve anchored off so many uninhabited islands and sandbars, but we never take it for granted. It never gets boring. We’ve met so many friendly people who’ve helped us in our steep learning curve. What is it to be a cruiser? Somehow, I’d figured that over time it would become obvious.

Recently, though, I’ve realized something profound. I’d been observing all the sailing folks we’ve met, trying to ascertain how we fit in to the cruising life, what kind of sailors we are, which box we should slot ourselves into. And that was exactly the wrong perspective to have. The truth is, like anywhere, you invent your own life and your own style of doing things. You carve out your own comfort zones, and then as far as sailing goes, you push that envelope all the time.

Every time we find ourselves in a big storm with zero visibility, whipping winds, huge waves tossing us around, lightning snapping the water surface all around us, my boundaries are pushed a bit further.

Then there are the days where your boat is anchored across from the Manhattan skyline and you find yourself dressed in your ‘cruiser uniform’: flip flops and backpack, navigating the eclectic neighborhoods of NYC on foot. You have to pinch yourself on those days.

I pinched myself in the crystal blue turquoise waters of the Exumas in the Bahamas. It was like a different world. Yet what connects the two worlds is us, and our experience of both, and all the amazing worlds in between.

For the first two years I imagined being a cruiser was living on your boat in tropical heat, with no a/c, swimming daily, listening to the ‘cruiser net’ on the VHF radio, and immersing yourself to some extent in the politics of the cruiser community in the islands. It was all about rum punches with frequent squalls, anchoring in clear sandy bottom places, spotting sting rays and turtles, enduring rough seas from island to island.

The past two years I’ve learned so much more. Cruising is what you make it, where you make it.

Being in the states for the past six months I haven’t swam once, haven’t seen the bottom when we drop anchor in just as long, and our VHF radio is constantly buzzing with local fishing boat traffic. I’ve been wearing long pants and fuzzy slippers and I can’t remember when I last broke a sweat. Cheap gold rum has been replaced with red wine and tots of whisky to warm the chilled soul.

But still, we are the observers. Taking our home with us, from bay to bay, city to village, climate to climate.

The rest of the world lies ahead, undiscovered, beckoning a couple people who live on a boat, who crave the adventure and the thrill of the unknown. I’ve abandoned the idea of fitting into a box, choosing instead the fluid, non-defined beauty that is this experience. Like the ocean herself, we are moving.

Written by Holli Holdsworth

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