How it started

Grand Cayman, on our honeymoon.

We booked a private boat trip with Crazy Crab Cayman and it genuinely took our breath away. We snorkeled. We saw stingrays. And we had the entire boat to ourselves.

What made it land wasn't the destination — it was the contrast. Around Stingray City we could see the other boats: packed, everyone jostling for a view, for space, for a turn. Meanwhile our captain asked what we wanted to do next and then simply did it. We changed the itinerary partway through, more than once, because we could.

That's not possible on a boat with thirty strangers and a fixed schedule. It was the first time either of us understood how different a day on the water feels when it's actually yours.

Keith flew the drone, Dede shot and edited, and the articles that followed ran on their website. The relationship stuck, and so did the idea — along with the habit. Both of us shoot on every charter now, which is why you go home with photos of your own day instead of everyone's camera roll being of each other.

Why Florida, and why "Wayward"

We looked seriously at Bocas del Toro in Panama first. The water was right, the setting was right, but the finances weren't. Florida's Gulf Coast turned out to be the better answer anyway — turquoise water, warm enough to swim most of the year, and wildlife you can count on.

The name

Keith chose it. The small islands out here — the keys — aren't fixed. Storms and tides reshape them. Sandbars appear, shift, and vanish. In 2024, a hurricane season carved a new island off the northern tip of Honeymoon Island that has since separated completely.

Wayward means exactly that: something that won't stay where you put it. It's an honest name for a coastline that redraws itself, and for a company built around going wherever the day actually leads.

Meet the crew

Captain Keith

USCG-Licensed Captain

Eleven years as a U.S. Navy submariner. Anyone who can spend months at a time underwater and come out still loving the water was always going to end up here.

After an injury ended his military career, he went into nursing — cardiac care, the kind of work where staying calm while things go sideways is the entire job. That's the temperament he brings to the helm.

He's also a former Navy diver, which is why he reads water clarity and conditions the way he does.

Eleven years of standing watch left him with a habit he can't switch off: when guests are in the water, he's watching it. A manatee drifting under the anchor line. A current picking up. A boat coming in faster than it should. Six guests is about the number one person can genuinely keep track of, which is part of why we cap it there.

He gets in the water too — finding live sand dollars, showing kids what's on the bottom.

Dede

First Mate

A published travel writer — International Living Magazine, mostly pieces on beaches and tropical destinations, which in hindsight looks like a long run-up to this.

She's a trained photographer — coursework plus years of shooting for her own stories, because travel writing doesn't work if you can't also make the picture. She shoots, edits, and shapes the footage into something worth keeping.

Between the two of them, every charter comes home with candid photos rather than posed ones — sent to you afterward, no charge, no upsell.

We met in Arizona, both working in hospitals. Neither of us was near an ocean at the time.

Tessa

Sea Turtle · Ocean Advocate

Tessa came from the turtles we'd watch dart around while we were out on jet skis. She started as a 3D character and evolved into who she is now.

Her story: we were out trying to fish a stray balloon out of the water and struggling to reach it, when a sea turtle surfaced out of nowhere and nudged it toward us.

Balloons and plastic bags look like food to a sea turtle. She was, we like to think, pleased that someone was bothering. She's been our mascot ever since, and she'll be turning up in videos soon.

What a day with us is like

Every charter is private. The whole boat is reserved for your group — up to 6 guests — with no strangers aboard and no fixed route. Captain Keith builds the day around your interests, the tides, and the conditions, and adjusts as it unfolds.

That flexibility isn't a marketing line. It's the specific thing we experienced in Grand Cayman and the reason this company exists.

Where we go

We depart from both sides of Pinellas County, and they're genuinely different days rather than the same trip from a different dock.

From the Clearwater side — Caladesi Island, Honeymoon Island and the new island off its northern tip, Anclote Key, and Three Rooker with its bird rookery. See everything there is to do on the water in Clearwater, or if you're staying north, charters near Dunedin.

From Maximo Park in St. Petersburg — Fort De Soto's sandbars, Shell Key Preserve, Passage Key, Egmont Key with its submerged Civil War ruins, and the Sunshine Skyway from underneath. See what's on the water near St. Pete Beach.

The charters themselves

Popular days include dolphin and wildlife watching, sandbar retreats, snorkeling, shelling, island hopping, sunset cruises, and family charters.

Not sure which suits your group? The FAQ covers most of it, or just get in touch and we'll talk it through. What to expect on your first charter is a good place to start if you've never done this before.

Why Tessa matters to us

A mascot could easily be decoration. Tessa isn't.

The balloon story is true, and the reason it stuck with us is what it represents. Sea turtles mistake floating balloons and plastic bags for jellyfish. They eat them. It kills them. We see debris out there regularly, and we pick it up when we do.

Tessa is how we talk to guests — especially kids — about keeping this water healthy without turning a good day into a lecture. If a family leaves knowing why that stray balloon matters, that's worth as much to us as the photos.