10 Things I Learned While Sailing

By: Naomi Matlow

The sailboats have been docked, the lines tidied up, and there is not a full bottle of rum in sight. That means the Unsettled crew is back at their respective ports after a week of literally throwing caution to the wind while island hopping in the British Virgin Islands, but we’re not anchored for long.

It was a week of adventuring on open waters in every shade of blue. While not my first Unsettled adventure, it was my first time sailing with the Unsettled community.

Though impossible to sum it all up in words, here are ten things I learned on the journey worth passing along.

  1. It’s a social experiment of sorts. Imagine 25 strangers from around the globe on three boats, who learn to more than successfully live, sleep, cook, eat, sail, share, laugh, dream, and sometimes deck shower, together for a week in close quarters (with one shared travel-size bottle of soap).
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2. Sailors have a different word for EVERYTHING. And port and starboard (left and right… if your facing the front of the boat) is just the beginning… A rope is a line, the boat speed is measured in knots, a bathroom a head, a steering wheel a helm… and the list goes on. But this new vocabulary and new reality sets in right when that mainsail goes up for the first time. 3. The best lunch you may ever have is a peanut butter and jelly sandwich with your crew in the cockpit while the boat is set on autopilot. Sometimes you just have to lose track of time, feel the breeze, keep your phone on airplane mode, and just be. 4. Getting your full crew in the tiny dinghy, without a man overboard, is an art form. But an art form you will no doubt perfect by day 2. Trust us. 5. The boom is called a boom for a reason, and when your captain says to watch your head, they mean it. Fortunately, none of us learned this the hard way.






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6. Take advantage of those marina land showers. Fresh water is a luxury for a sailor, but crew showers on the transom after a group swim, is an even bigger luxury.

  1. There are so many ways to maximize that one sriracha bottle to feed your full crew for a week. Pasta sauce, mahi mahi on the grill… that bottle is good until the very last drop.

  1. Deserted island bonfires under a full moon is pure magic. You may have to remind yourself that you are not in a movie, and you didn’t know anyone around the fire more than only a few days ago.

9. While our Unsettled crew may have been from 15 countries, and from their mid 20’s to late 40’s, they can all break out some serious dance moves in Caribbean island bars like no one’s business. And damn, can they limbo.

10. Keep an eye on your ship’s pirate flag. Or be forewarned that if you steal one from another crew, you may be starting a boat war, and could end up with a very large and stinky crab shell hidden somewhere in your berth. But that’s pirate life, right?

Though we may have all now reached our harbors, we’re raising those jibs, tacking for days, and setting sail once again this January in the Bahamas and this June in Greece. Sign up today to get on deck!

Fair winds…


Unsettled is a global community for those who live and work differently. 

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