2/2 on Sails for the Florida Keys Children's Shelter

Some trips you run for fun. Some you run for fish. This one, we ran for the kids.

The Miss Penny donated a full-day charter to the silent auction at the Best of the Upper Keys 2025, with all the proceeds going to the Florida Keys Children’s Shelter — the folks who provide emergency housing, counseling, and a safe place to kids and families across the Keys, free of charge, to the ones who need it most. A $2,000+ day on the water for a cause worth every dollar.

Chad ran the boat. I ran the pit. Our auction winner Richard Weinstein rolled up to the dock with Anton, Seth, and Barry ready to go, and we went to work.

The fish cooperated.

The Day

Clean morning. Light breeze. The kind of Saturday that makes you wonder why anyone stays on land.

Set the spread early and stayed busy. We went 2-for-2 on sailfish — two bites, two hookups, two clean releases. No long soaks, no “he ate and let go” heartbreak. Both fish ate right, jumped hard, came boatside, got the leader touched, and swam off strong. If you measure a trip by sail conversion, that’s as good as it gets.

Sailfish #1 putting on a show. This is what everybody books a Keys trip hoping to see.

Between the sails we kept rods bent on the reef and the edge:

• Cero mackerel — plenty of them, and one in particular was destined for bigger things (more on that in a minute)
• Mutton snapper on the reef
• Mixed-bag action that kept all four anglers rotating through and nobody sitting on their hands

The Crew

Chad on the wheel, making it look easy. That man’s got a sixth sense for where the sails are holding, and Saturday was no exception.

Richard, Anton, Seth, and Barry took turns in the chair — everyone got bent. That’s the mark of a good charter: nobody leaves the boat wishing they’d been next up.

Leader touched, fish in control, release clean. 2-for-2 on the day.

The Sushi Encore

Here’s where it went from “great day fishing” to “once-in-a-lifetime.”

The crew ran the fresh cero over to The Islander at Ocean Reef, where Executive Sushi Chef Eric Andreu broke it down into a full platter of nigiri. Same-day cero mackerel, caught that morning, on the sushi bar by that evening. You don’t get that at a restaurant. You catch it yourself and hand it to a chef who knows exactly what to do with it.

Chef Eric Andreu’s handiwork. From the cooler to the sushi bar in a single day. That’s the Keys.

Why We Did It

The Florida Keys Children’s Shelter takes care of kids and families in tough spots — emergency housing, counseling, a safe place to land — all free of charge, all up and down the Keys. When the Shelter team asked Miss Penny to kick in a charter for the auction, there wasn’t a question to think about. You want the DirtyBoat behind a cause, this is the cause.

Huge thanks to the Shelter team for putting the event on, to Richard Weinstein and his crew for bidding generously and fishing hard, to Chef Eric at The Islander for the sushi send-off, and to everyone at the Miss Penny for making the boat available.

Good fish. Better cause.

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