Hurricanes & Sailboats Don’t Mix

My Pearson 365 survived Hurricane Milton, but several of my nearby dock neighbors suffered sadder fates. Thanapipat/Adobe.Stock

One of my favorite movies of the past several years was The Florida Project, director Sean Baker’s masterful take on the seedy underside of the Sunshine State as experienced by a feisty 6-year-old in a rundown budget motel just a stone’s throw from Walt Disney World (code-named “the Florida project” during its planning stages). For the past couple of winters, I’ve conducted my own personal Florida project, living aboard my Pearson 365, August West, in a tiny cove on Sarasota Bay tucked behind a barrier island called Longboat Key.

I was aware from the outset that I was tempting fate by keeping a boat on Florida’s west coast during hurricane season, and was especially fearful last summer when the steamy, adjacent Gulf of Mexico topped out with seawater temperatures approaching 100 degrees. I was terrified that the soupy brine would turn into an incubator for tropical activity, which proved to be precisely the case. We were mostly spared the wrath of brutal Hurricane Helene, but two short weeks later, when Hurricane Milton made landfall on Siesta Key a handful of miles south of my berth, my little marina was creamed.

Unlike several of my dock neighbors, which sank or were dismasted, my rugged old Pearson—built like the proverbial brick outhouse back in the mid-1970s—remained afloat, its bilges dry. But August West did get punched in the nose: The bow pulpit, anchor platform and headsail furler were swept away, along with several forward stanchions. All repairable, but now I’m facing several actual projects. Boat projects.

All of which has led me to some existential questions. I’m seriously grappling for answers. Should I double down, make the repairs here, and cross my fingers that Milton was “the big one” and all shall be well going forward? Or do I cut my losses, bail out, and point that scruffy bow northward toward my Rhode Island home waters? After all, August West may not look like much at the moment, but it’s still a perfectly capable, oceangoing sailboat.

At this precise moment in time, the option of bailing seems to be the more sensible one.

Part of this has to do with the marina. Several of the docks took direct, wipe-out hits, and it’s unclear when or if the condo association that owns them will wish to invest the considerable sums it will take to fix them. After all, it’s wrestling with the same question I am: When’s the next one coming?

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It’s impossible to arrive at a comfortable, optimistic answer. You can debate “the climate” all you want, but the fact is, the Gulf Coast has been belted repeatedly during the past few years. It will be years before Fort Myers Beach and Sanibel Island will ever be the same, and you can now add Siesta Key, Longboat Key and Bradenton Beach to that sad list. What’s that line about insanity—expecting different results from the same repeated activity?

The Florida Project concludes on a devastating note. The little protagonist, in the face of youthful tragedy, makes a break through Disney World. She runs and runs, bound for the Magic Kingdom. It’s all so lovely, so fresh and polished and inviting.

It’s all a bloody mirage.  

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