From Freezing My Nuts in Annapolis to Warming Hearts (and Maybe More) in Key West.
So, my whole blogging career (if you can call it that) started out as “Boredom Logging.” Yeah, I was literally logging my boredom. Picture it: winter, no woman to argue with about thermostat settings, no one to say, “stop leaving your socks in the galley,” just me on a boat in the cold like some frozen-out hermit crab.
Most sane boat people pack up and head south when the temps drop. But not me. Nope. I got dumped in September and spent a good 2–3 months doing that pathetic ex-boyfriend thing—replaying arguments in my head, texting essays, Googling “how to win her back,” and praying she’d suddenly remember I’m charming. (Spoiler: she didn’t.)
So, I wintered in Annapolis, freezing my ass off. But this year? This year I’m going south like a damn snowbird with a plan.
Why I Keep Blogging (and Why You Keep Reading)
Turns out I like writing this crap. It’s cheaper than therapy, safer than drunk texting, and close to 400 of you are rubbernecking and reading them every time I hit “publish.” So poo-poo to the naysayers.
For the last three years I had someone editing, censoring, and deleting the silly stuff I wanted to post. Not anymore. This is all me now, baby—raw, uncut, uncensored.
And yes, I know some of you (moms, especially) are lurking, waiting for me to announce that I’ve got a woman again. I get it—you want me coupled up, like I was with Donna. You want the Hallmark ending, where I sail into the sunset with someone who actually puts up with me. Don’t worry, we’ll get to that.
The “Disability” Update: MOGAD
Quick health detour. Most of you know I tell people I have Multiple Sclerosis because it’s easier than launching into a TED Talk on neurology at the bar. But truth is, what I actually have is MOG Antibody Disease (MOGAD).
Think of it like this: MS is when your nerves get stripped and stay stripped. MOGAD is more like your nerves get dinged up, but with the right meds they can grow back, like Chia Pets.
Latest MRI report came back, and—good news—my five-hour long weekly injections are working. The spine looks cleaner, the brain hasn’t gotten worse, and my optic nerve is holding steady. Basically, I’m like a used car: still drivable, but you wouldn’t want to take me on a cross-country road trip without roadside assistance.
Boat Projects: Sewing My Ass Off
The big project right now is sewing an awning for the rear deck/solar arch. And let me tell you, sewing something this big is like trying to wrestle a drunk octopus into a prom dress.
I had to stitch three giant pieces together, and at one point Joe had to feed fabric into the machine while I tried not to sew my fingers to the Sunbrella material. (If I lose a finger, do I qualify for another disability check? Asking for a friend.)
But damn if it isn’t looking good. Tan awning with black grommets done to match the teak deck. Stylish. Sexy. Functional. I’m basically the Vera Wang of boat canvas.
And now that I realized I don’t need to sew in a window to see the mainsail, I’m already planning to add 900 more watts of solar next summer when I return to Annapolis. Ohana’s gonna be greener than a Prius at Burning Man.
Charters: Still Raking It In
Still loving the weekend charter hustle. Four little trips in a weekend and I’m walking away with two grand. I don’t know where else you can make that kind of money for enjoying being out on the water chatting with (90% of the time) bachelorette parties… on someone else’s boat!
Afterward, I get to dink back to Ohana—anchored out in Annapolis harbor—to freshen up. Then it’s into town for dinner and drinks, playing tourist in my own backyard. Not a bad gig.
Scuba: Back to School
Colleges are about to start back, which means I’ll be teaching my first scuba class! First gig I get to teach is Salisbury State!! I’ll get their pool and classroom stuff sorted, but I’m dodging the checkout dives in the freezing quarry. By the time they’re ready to get wet in that chilly quary, I’ll be in sunny Key West, sipping rum and pretending to grade papers.
Boat Shows & Dock Hustle
So the plan is to grab a ball in Downtown Annapolis around my birthday (September 13—ladies, mark your calendars 😏) and spend a month there through the two boat shows.
For the Powerboat Show, I’ll be at AM/PM Marine helping sell their Regal line of boats. Then for the Sailboat Show, of course, I’ll be at the Antares booth, grinning like a kid at Christmas.
The routine is starting to make sense: leave after the shows every fall, head south for the winter, then back north in time for summer and the Blue Angels flyover in Annapolis. Perfectly syncs with hurricane season and keeps me out of trouble (well… most trouble).
Meanwhile, Pine Narrows Yacht Haven Marina is working through their list of boats that need winter slips. Looking good I’ll have a renter this year. Even cooler—Antares is going to use my dock to prep one of their boats (Sorella) for the show. Once they clear out, my renter moves in. That rental income? More than covers the cost of my Key West mooring. My dock is literally paying for my rum budget.
The Big Plan: Southbound!
Here’s where it gets exciting.
Route: offshore, about eight days, sailing through the night. Crew: Joe (trustworthy) and maybe one other sucker I rope in. And here’s the bombshell for the moms—there’s a slight possibility I’ll have a roommate for the adventure.
Yep. New Lisa. She loves boats, her friends say she should live on one, and she’s “working her plan” to get into this lifestyle. And—bonus—she might just join me in Key West. (Don’t freak out, moms, it’s just a buddy system. You know… safety. Yeah, let’s call it that.)
Wrapping It Up
So here I am: 30 days out from leaving my dock. Engines prepped. Generator tuned. Locks installed. Surveillance cameras up (because even pirates shop around). Carpentry tools and bike loaded back on board.
And now with my fancy new PredictWind service I’ll be tracked like a bad Tinder date. Once I figure it out, it’ll:
Route me based on weather and comfort.
Let friends/family stalk… er, track me as I travel.
Sync straight to my B&G plotters so I see it in the cockpit.
Even tattle if Ohana drags anchor or gets pushed around.
It’s happening. This time I’m not wintering alone, cold, and bitter. I’m heading south, baby.
And whether I end up with more solar panels, more students, more grommets—or hell, even more women stories for the moms—y’all are coming along for the ride.
Stay tuned. It’s about to get fun.
