Family of Four Journeying to Open Waters

An Overnight Passage: Marco Island to Key West

On June 5, we set out for our third overnight sail – this time from Marco Island to Key West. It turned out to be our most exciting one yet.

We pulled anchor in the late afternoon, around 5:30 or 6:00 p.m. Dinner was on the stove, Barrett was juggling some charting and kid-wrangling, and spirits were high as we pointed south. The air felt beautiful, buzzing with that mix of anticipation and nerves that comes with an overnight run.

Storms hovered on the horizon but never touched us. I took the first shift and kept us steady, even as the weather radar lit up in the distance. Through the night we had good wind – mostly 16–17 knots, with gusts creeping into the low-to-mid 20s. The forecast hadn’t quite captured the reality: rockier, rolly seas with bigger swell than expected. It’s becoming a bit of a theme – no matter how many times we check PredictWind, the ocean writes her own script.

Still, the sunrise was magic. After a long, intense night shift, Barrett got some rest while I took the helm and watched the sky turn from ink to watercolor. By morning, the water shifted to the stunning turquoise we’d been dreaming of – our first glimpse of the iconic Key West palette. We were giddy, knowing this was the kind of view we’d get to soak in for the next few weeks.

Our plan was to grab a mooring ball at Garrison Bight, just around the corner from Key West Bight Marina. Protected? Yes. Pretty? …Not so much. The water was murkier there than the clear shallows we’d just passed through. But we were tired, happy, and ready to tie up.

That’s when the real comedy began.

Mooring Ball Grab Attempt #1: I leaned over with the boat hook to snag the mooring eye, only to find it stuck. With too much momentum, I had to let go – sending the boat hook floating away. (Thankfully, it bobbed up “stick side” first, sparing us a loss and any lectures.)

Ball Grab Attempt #2: We lined up again, this time certain we’d nail it. Nope. Same problem. This time the hook went in the water again and started sinking instead of floating. Cue another scramble.

Ball Grab Attempt #3: We regrouped. I took the helm alongside Barrett. He lined us up, then ran forward and grabbed position on the bow. With one last try – success! He hooked the mooring ball, secured the line, and exhaled in relief.

Showers. Laundry. A tiki bar around the corner. Bingo (we even won!). Live music, ferrying laundry, fish-cleaning lessons. That night, we slept like rocks, grateful for our safe arrival in Key West.