Or, How I Forgot That “Safe” Doesn’t Always Feel That Way

To maximize our time at the Bimini Islands, I planned a night sail across the Gulf Stream from Fort Lauderdale—a 13-hour crossing that I knew well. A swift trip even if translantic in nature. I wasn’t trying to impress anyone. I was simply making the most efficient use of our trip. I had checked the forecasts. A two-meter swell was rolling, but that was within my comfort zone. It usually meant good sailing and good sleep, especially for passengers.

What I didn’t account for—what I should have thought through more carefully—was how it would feel to someone with no experience on a large vessel in the open sea.

The Gulf Stream is a force. Add to that a three to five-knot current heading north and a 25-knot wind blowing south, and you get sharp, stacked waves. Manageable—but energetic. Still, I wasn’t concerned. I had outfitted the biggest boat I could safely run solo, retrofitting it with gear and systems that brought the required crew from three down to one: me.

But as nature often does, it upped the ante.

A squall moved in, and soon the breeze averaged 45 knots. Not gusts—sustained wind even though it seemed to be shifting as quickly as I could respond with various sail plans. The seas ramped up quickly. Swell became walls. I adjusted sail plans, balanced the rig, and kept the boat pinned down for stability. Why have a bare pole—too unstable and slower is a waste of time. Controlled motion was better than chaos.

Then the rain stopped going sideways and looked like it was going up. Then the mainsail jammed.

I had not planned for this maneuver, but thankfully, I was not clipped in so climbing the mast did not change any risk I was already assuming.

That’s when I realized I couldn’t move. Not because of the wind or waves—but because my fiancée had latched onto me with both arms and most of her soul, convinced this was how it ended. She was genuinely terrified, unfamiliar with the rhythm of big water.

I gently pried her loose, reassured her, and redirected her hands to something solid and stationary. She later let me know what the wind she couldn’t hear a word I said. Then, with water slapping my face like buckshot and the rig shuddering above, I climbed and got the sail sorted.

The rest of the trip was a series of adjustments, both nautical and emotional. I trimmed sails, balanced motion, kept an eye on our course—and silently reminded myself that “safe” to me might still feel like a storm to someone else.

When we reached Bimini, soaked but intact, she told me it was the worst trip of her life. Then she added, “And the best.”

That contrast seems to follow me. A few weeks later, staring at a mountain with a 45° slope, she said:

“I just imagine you hacking up that thing with a machete while riding your motorcycle.”

She might be right. And 26 foot waves at 15 knots of hull speed might’ve been a bit much.