We Did the Unthinkable: A Jet Ski Day Trip to Pine Key and a Floating Picnic in Tampa Bay
Full throttle, wide-open water, and a storm rolling in over downtown Tampa — that's what a "regular" Sunday looks like these days. We loaded the jet skis at Williams Park in Ruskin like we always do, ran out to Pine Key... and then did something we'd never tried: anchored right in the middle of Tampa Bay for a full-blown floating picnic. If you've ever wondered whether you still have days like this in you, keep reading — you do.
A Regular Stop That Never Gets Old: Pine Key
Pine Key has been one of our go-to spots for years, and it's taught me something about showing up even when things get hard. The tiki bar out there took a direct hit during Hurricane Idalia — collapsed completely — and the owners are still rebuilding it, piece by piece. That's the kind of grit that keeps this whole stretch of coast alive, and it's worth noticing. We anchor our jet skis front and back out there, because when a big ship comes through the channel, the wake will flip an unanchored ski in seconds — so the moment that boat appears, everything stops and it's all hands on deck. It keeps you sharp. It keeps you present. And every weekend, we make a point to stop by the same family who's been selling hot dogs, Italian ice, and boiled peanuts out there for years, because supporting people building something themselves is part of why we keep coming back.
Why We Left the Island — And Why You Should Say Yes More Often
After about an hour on Pine Key — swimming, talking to people, soaking it in — it would've been easy to just head back to land for lunch like we always do. Instead we asked a simple question: why not right here? So we anchored in the middle of Tampa Bay, Davis Island behind us, a storm pouring down on the city skyline in the distance, and had a full picnic floating on open water. We'd never done that before, not once in all our years out here. Turns out one of the best lunch spots we've ever found was hiding in plain sight the whole time — we just had to decide to stop and take it. That's the whole game after 50: stop waiting for the perfect moment, and start making the moment.
Watch the Full Adventure — And See What's Still Possible
The anchor drill when the ship comes through, the storm rolling in over Tampa, the taste test — all of it is in this week's video. Watch it, and really picture yourself out there. This isn't a highlight reel of something out of reach. It's a normal Sunday for two people who decided retirement was going to be active instead of quiet. Give it a watch, and let me know in the comments if you've ever tried kiwi berries — or if this is the push you needed to plan a day like this of your own.
This Is What Retirement Looks Like — And What Yours Could Too
Nobody told us we'd be eating lunch in the middle of Tampa Bay when we retired — but that's kind of the point. Retirement isn't about following a schedule somebody else built for you. It's about noticing you can do something a little different on a random Sunday, and actually doing it. If a floating picnic in open water sounds like "too much" for retirement, I'd push back on that, respectfully. It's not too much. It's exactly enough.
That's the whole idea behind The Usable Years. Retirement isn't a finish line — it's actually the starting line. Everything you spent decades working toward — the career, the family, the grind — that part is done. This is the new start, and it's one that actually matters. It's a stretch of time you still have full use of, and the number of years you're strong enough, mobile enough, and healthy enough to actually use it is smaller than most people plan for. Every "unthinkable" thing I do out here — anchoring in open water for lunch, running jet skis every weekend — happens because I built my retirement around staying capable enough to keep saying yes to it. You can build yours the same way, starting today.
If you're picturing rocking chairs instead of jet skis when you think about retirement, this book will change that. It's not a financial planning guide — it's a push to think seriously about the years you have left before your body starts setting the limits for you, and what you're going to do with them while you still can. Read it, and then go plan your own version of a floating picnic. I promise you have one in you.
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