Change of Plans: My Quest for a First Mate (And Maybe a Little Sun)
Well, readers, gather ‘round because Captain “Ohana Dave” (that’s me) has had yet another change of plans. But this time, I’m not just winging it. I’ve had a little help from what has turned into my “life coach” (a.k.a. “Old Lisa”), who’s been in my ear lately, helping me refocus. Her sage advice? “Stop obsessing over finding your next first mate and focus on something bigger… more complex.” And she’s right.
Funny thing, though — I can’t help but feel like God’s been steering me all along. He works in mysterious ways, doesn’t He? Nudging us through the people we meet, guiding us down unexpected paths. Lisa’s advice, Donna’s memory, and all the connections I’ve made over the years — it’s almost like He’s been laying the breadcrumbs for this new journey. So instead of chasing the sunset to the Bahamas this winter (cue conch fritters and solitude), I’ve decided to tackle something way more meaningful.
Enter Plan C: Key West — Where the Party Never Ends!
Why Key West and Not the Bahamas?
Sure, the Bahamas had its perks — sandy beaches, clear blue water, and plenty of alone time. But the more I thought about it, the more I realized I needed a deeper purpose. And that’s where Donna comes in.
I’ve been carrying her ashes aboard Ohana, and one of my life goals has always been to take her somewhere in the Keys and turn her into a natural reef. Not just any reef — I’m talking Donna style. The plan? Find a hobby horse (because besides diving horses were her thing), fill it with concrete and her ashes, engrave something meaningful — her name, her PADI Instructor number, and the dates she graced this world — and mark the GPS coordinates for future visits and dives. I’d invite friends and family down to join me as we set her final adventure in motion.
And honestly? I can’t shake the feeling that God is giving me this opportunity at just the right time. Living 6 months in Key West gives me plenty of time to make this happen. It’s the perfect place to find the right spot, the right horse, and create something that honors her in a way that feels true to who she was.
Why Not Key Largo?
I did give Key Largo a fair shot. I know the biggest dive shop there, and I’m pretty sure they’d hire me on the spot. I even found a slip right next to their docks — sounds perfect, right? Wrong. The slip alone costs a jaw-dropping $3,000 a month. That’s more than my entire boat budget!
And while Key Largo’s got great diving and fishing, the nightlife? Let’s just say I’d be in bed by 8 PM, with nothing but the sound of distant fish burps for company. I need a place with a little more energy… and that’s where Key West shines.
Enter Plan C: Key West — Where the Party Never Ends!
So now I’m eyeing Key West — where there’s plenty to do, an endless supply of colorful characters, and the kind of nightlife that’ll keep me busy enough to forget that I’m 58 and retired. But making this happen is going to take some work…
Step 1: Get Certified, Stay Legit
To make myself irresistible to dive shops down there, I need to finish getting my PADI dive instructor cert. Pair that with my 50-ton USCG captain’s license, and I’ll be a one-man water adventure package. And just to seal the deal, I’ll casually mention that I’ve been training under the guy (John Kiser) who’s been recognized by PADI for certifying more PADI open water divers than anyone on the planet.
Throw in the fact that I’ve taught at the US Naval Academy and half the colleges in Maryland, and they’ll probably just hand me the keys to the dive shop and a whistle. But timing is everything — the next PADI Instructor Exam (IE) in my area is Memorial Day weekend, and after that? Not until August. So, Memorial Day is my target. I’m locking that in like a diver setting their dive computer before a deep wreck dive.
Step 2: Find a Home for Ohana
Slips in Key West? Outrageous. And honestly, Ohana doesn’t need one. So, the plan is to snag a mooring ball in the city mooring field. For under $400/month, I get:
✅ A ball in a community that’s not crime-ridden
✅ A dinghy dock (because rowing in circles loses its charm quickly)
✅ A bike lock-up (because I’ll need my wheels)
✅ Even laundry facilities (which I’ll probably ignore because, let’s be honest, I will live in a swimsuits, and Ohana’s washer and drier can handle those.)
The only hiccup? Mooring balls in Key West are scarcer than a sober tourist on Duval Street. I think you can reserve them, but that’s a detail I’ll have to dig into… fingers crossed.
Step 3: Plotting the Great Escape
How do I get Ohana to Key West? That’s the million-dollar question. I’d prefer to sail the whole way down the outside (ocean route, not the ICW), but there’s one tiny problem — I get seasick in rough water. And the waters off Cape Hatteras? Rougher than a hangover after a Key West pub crawl.
So, I have options:
Hire a Captain — I know a guy from Chronic Sailing who could help. If I need to get there quickly for work, this may be worth it.
Find-A-Crew.com — Maybe I’ll snag an adventurous soul who knows a thing or two about boats.
Ask My Boys? — Ha! They’d be about as useful at sea as a screen door on a submarine.
If I land a job in the Keys before I leave, I will probably just hire a captain and power through as fast as possible. I can’t take a chance of being out there and getting seasick unable to address emergencies.
Step 4: Prepare for Key West Living
It’s not just about getting there — it’s about staying there. Here’s my new checklist before I make the leap:
🩺 Find a Reliable Place to Ship My Meds — Worst case, I can have them shipped to the dive shop I work out of, but I need a backup plan in case that’s not an option.
🚗 Figure Out What to Do with My Truck — Do I turn in the tags and let it sit? Or find a special policy that covers me for the state so I can quickly reactivate it when I return?
⏰ Set the Dates I’m Heading South — Once I lock in my departure, I can rent out my slip at Piney Narrows for the winter, which will essentially pay for the mooring ball I’ll grab in the Keys. Win-win.
Worst-Case Scenario: Plan D(esperation)
If nothing works out — no instructor cert, no job, no crew — I’ll go solo down the ICW, pop out for one overnight sail from South Carolina to Florida, and then stick to the inside. I’ll take my sweet time, soak up the journey, and chat with folks along the way. At least that way, I won’t freeze my butt off in Maryland, and I’ll have some company on the trip.
So, What’s the Big Picture?
This isn’t just about skipping the Bahamas — it’s about taking a detour that feels right. Key West isn’t just a party destination (although, let’s be honest, that’s a bonus) — it’s where I can honor Donna’s memory, chase my dreams, and maybe even find that elusive first mate who’s ready to sail through life’s adventures with me.
And through it all, I can’t help but feel like God’s hand is guiding me.
Every unexpected detour (like 4 yrs w/ the ex), every challenge (MOGAD), and every connection (“Old Lisa”) has led me to this moment — and I’m ready to see where this next adventure takes me.
So, who’s coming with me? 😉
