You Can’t Fake This Stuff: A Charter Story

I’ve developed a pretty good nose for trouble. In the charter world, vetting guests is nonnegotiable—and when someone’s résumé doesn’t quite pass the sniff test, I dig deeper. We all keep what you might call a “bad boy list.” If a guest claims to have chartered elsewhere, I pick up the phone and verify it.

One client—let’s call him Steve—raised red flags early. Mid-40s, acting like he’d been around the block but couldn’t produce a single solid reference. “I race in Chicago,” he claimed. “Done a couple of Macks.” He was tossing around offshore-racing credentials that I couldn’t confirm, and then dropped a big name: Gary Jobson. He called him “Gary” and said he would vouch for him.

I know “Jobbo.” He and his wife were staying on one of my boats in Key West, Florida, that very week. So, when Steve and his father—a seasoned, capable sailor—were ready for their checkout, I decided to handle it myself. The handover started late, around 6:30 p.m. As we walked through the safety and systems checklist, it became clear that Steve was out of his depth. His answers were vague, his confidence unearned. His dad watched him sideways the whole time.

I pulled the father aside and asked, “Would you be comfortable running the boat?”

“Absolutely,” he said. “I just thought I’d let him take the lead.”

“Well,” I told him, “I’m not totally comfortable with his level.”

He nodded slowly. “Yeah, I’m not sure what he’s thinking either.”

At that point, I walked a few slips down the dock and found Jobbo. “Hey, Gary,” I said, “I’ve got a guy here who says he knows you. Mind coming to meet him?”

Gary smiled. “I’d be delighted.”

We all gathered topsides—Steve, his dad and me—just in time for Gary and his wife to walk over.

“Steve,” I said, “this is Gary Jobson.”

Steve turned pale. His dad laughed, shook Gary’s hand and said, “Big fan.”

I looked at the son and said, “Darlin’, I think your daddy’s going to be running this trip. You good with that?”

Steve stared at his shoes. “If he is, I’m good with it.”

We redid the paperwork, reviewed the systems again, and off they went. They had a great trip—and to their credit, they came back to charter with me several more times.

I told him then, and I tell everyone now: You can’t fake this stuff. It’s not just about insurance. It’s about safety. You need to be able to handle the boat and the responsibility. This isn’t a rental car.

Ask questions. Take the time to learn. And if you ever start believing that you know everything about sailing, step off the boat. You’re about to get someone hurt.

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