Southbound on Ohana: Charting a Course to Key West (And Trying Not to Screw It Up)
Big plans are underway aboard Ohana — and I’m finally putting pen to paper (or finger to keyboard, after several hours of pretending my to-do list was just “manifesting itself”).
The dream? Sail down to Key West, live aboard in the city mooring field, and spend my mornings teaching people how not to drown, and my evenings captaining sunset cruises for tips, tans, and tales. Basically, semi-retirement with salt in my beard and sunburn in weird places. 🤪
But as any sailor — or single dad with a boat and a history of questionable ideas — will tell you: dreams like this don’t just happen. They require planning, persistence, and more than a few conversations with yourself that begin with, “What the hell were you thinking?”
First: I Need Crew (And No, That’s Not Code for “Therapist”)
Even the most seasoned sailor appreciates good company and an extra set of hands. I’m looking for someone cute, tiny, adventurous, capable, and chill enough not to panic when I burn the coffee or start arguing with the autopilot. Bonus points if they can cook, laugh at my jokes, and tolerate Jimmy Buffett and Calypso music on a loop.
Worst-case scenario? I single-hand the whole way down and spend my evenings giving pep talks to the chart plotter. (She listens better than most of my exes — and doesn’t roll her eyes.)
The Route: Outside or Inside (Like Most Emotional Decisions)
Two main options:
Outside Route: Faster, saltier, more adventurous. Also includes sailing through the night and around a very rough section outside Hatteras, causing me to vomit over the rail while cursing Poseidon. So yeah, this option requires crew.
Inside Route (ICW): Hug the coastline down to Cape Fear, bypassing the hell-stretch known as Cape Hatteras, where Poseidon goes to rage-cry and destroy dreams.
From West Palm to Key West, you’re basically paddling upstream through molasses, with the Gulf Stream pushing back like a bad breakup. Which once again, means: I should have crew.
In short: it’s like every relationship. Much smoother if you plan ahead, don’t ignore the warning signs, and know when to duck.
Boat Business & Logistics (AKA Adulting Afloat)
Rent my slip at Piney Narrows. Let someone else enjoy the ice-cold dock walks. The income I receive more than covers the monthly mooring in Key West.
Update insurance. Right now, I’m only insured for the Chesapeake Bay. That’s like having travel insurance that doesn’t cover travel. Time to expand coverage for the trip and the hurricane off-season down south.
Pause truck insurance. No need to pay top dollar for a parked vehicle — but I’d love to avoid the DMV every season. Hoping there’s a discount plan for “emotionally neglected” vehicles.
Find storage for the truck. Possibly with the boys. If they even notice. If not, bonus.
Dive Instructor Certification: Hurry Up and Wait
This has been the bureaucratic equivalent of watching paint dry underwater. I’ve been told the class is “just about to start” for months now. Spoiler: it hasn’t. Looks like I’ll miss the local PADI exam and will be driving to Florida for it instead. Yay. Another road trip with only my wetsuit and self-doubt for company.
Also: I need a new 2mm wetsuit. Mine are either 8mm thick and designed for Antarctic exploration, or so old they came with a cassette tape… and probably still smell like Donna’s shampoo from 1984.
Networking with Dive Shops (A.K.A. Strategic Flirting with Business Cards)
I don’t want to show up in Key West like just another salty drifter. I want to bring value. My current dive shop is ready to send students south for their checkout dives — we teach at most Maryland colleges, from Salisbury State to the Naval Academy to Western Maryland.
I’ll connect with the Key West shop ahead of time and ask for fliers I can distribute before I head south. “Hi, I’m Dave — captain, instructor, and walking billboard.”
Charter Captain Dreams (Cue the Jimmy Buffett Playlist and Mild Delusion)
Kai, one of my marina managers, used to captain for sunset cruises in Key West. He might have some contacts I can charm (read: beg) into hiring me. I’m aiming for a gig that says, “He’s dependable,” as well as “He won’t hit on the passengers…too much.”
Tech Tools for the Trip
Looking into a PredictWind subscription — not just for weather, but for:
Anchor alarms — so Ohana doesn’t wander off while I’m ashore living my best margarita life. With the Starlink I will be notified while on land if she moves.
Live GPS tracking — so family, friends, and curious exes can follow along. (Hi, “Karen!”)
A Reflection from the Helm (Because It’s Not All Jokes and Jib Sheets)
Every Sunday, latte in hand, I write these blogs mostly to talk to myself, giving myself something to do. It is also see how the Mass readings apply to this beautiful mess I’m building.
This week’s Gospel tells the story of Jesus meeting the disciples after they’d spent a night catching absolutely nothing. He says, “Cast the net on the right side of the boat, and you will find some.” They do — and the nets are bursting.
It hit me: sometimes the big changes come from tiny course corrections. Ask for help. Take a different route. Trust the process. I’m trying to listen for those nudges — even when they show up as dive shop voicemail greetings or a gale warning.
Thinking this way makes the dream feel a little lighter — and the idea of living aboard Ohana feel less like a cliché midlife crisis and more like a holy calling. With laundry. And way more luxuries than a traditional home.
Final Thoughts (And a Soft Pitch)
This isn’t just a trip. It’s a whole new rhythm. A floating life that mixes work, wonder, and just enough chaos to remind me I’m alive and slightly underqualified.
I’ll be teaching people to breathe underwater by day, and guiding them through pastel sunsets by night.
If you want to crew for a leg or just laugh at my misadventures from dry land, drop me a note. The adventure’s coming together — one mistake, I mean checklist item, at a time.
— Captain Ohana Dave
