The Adventures of Star and Her Motley Crew

The Adventures of Star and Her Motley Crew

Behind The Sails

Crew Calamities, Part 2: When Optimism Goes Overboard

On safety, ignored warnings, and what happens when bending your rules puts everyone at risk.

Sailing Star Hunter's avatar
Sailing Star Hunter
Mar 05, 2026
∙ Paid

Welcome to our weekly survival guide from the high seas, where plans unravel, the wind has opinions, and we question our life choices. If you’re here for glossy sailing fantasies, you may be disappointed.

This is a departure from our usual newsletter, focusing on the mistakes we made when it came to crew on Star Hunter.


Names and identifying details have been changed. This is shared not to shame anyone, but because these situations are far more common than people admit.


If you missed Part 1, here’s the gist: Our crew went from annoying to problematic overnight. Read it here: Part 1


You’d think after the last crew fiasco we’d be cautious. You’d be wrong. Very wrong.

We actually thought we were being careful. We had rules. Sensible rules. One of them was no one under 26. Life experience matters, and we wanted crew closer to our age. Naturally, we broke that rule almost immediately.

A former crew member asked if their friend could join. We met them on a video call, then in person. They seemed sensible. Respectful. Had sailing experience. Claimed to be handy. Apparently planned to get into carpentry.

So, we said yes.

Our assessment was… optimistic at best. Already exhausted from the emotional hangover of the previous crew, we let things slide. That was mistake number two. Possibly three. We’ve lost count at this point.

I am almost embarrassed to list what followed, but honesty is kind of our thing. Also, if we don’t laugh about it now, we might cry.

And hopefully it will help you learn from our mistakes.


Arrival & Early Red Flags

Our new crew arrived and began settling in. Since the previous couple had just left, we temporarily gave them their own room, explaining they’d move back into the bunk room once additional crew arrived. This was us being generous. Foreshadowing.

Almost immediately, Frazer was asked: “How do you feel about weed on board?”

We were very clear. Absolutely not. Not just because of rules, but because it would be drug smuggling and we are not criminals.

That question should have been our cue to say, “Thanks for coming, goodbye.” Instead, we smiled politely and carried on.

At that point, this was no longer about them, it was about our unwillingness to act on information we already had.

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