The Boat That Was Too Big (But Too Right)|Liveaboard Boat Florida

Life Afloat: The Boat Season, Episode 2: The Filter

When Linda and I started dreaming about boat life, we knew one thing right away.

Our boat wasn’t going to be shiny and new.

We wanted a “not so new” boat we could make our own.

Now, did we still go to boat shows and drool over the beautiful, new-yacht-smelling floating mansions?

Of course we did.

Nothing like walking through a million-dollar yacht to remind you that your dream is alive and your wallet is laughing.

Then we came down from the dream cloud and re-entered reality.

And here’s the truth.

We assumed we’d have to pay a lot more for THE boat we were dreaming of.

Then Florida did what Florida does.

Two hurricanes came through and rearranged half the Gulf Coast.

I’m not saying the universe, Mother Nature, or God sent hurricanes so we could find an affordable boat.

That wouldn’t be right.

But I am saying this:

There are a lot more motivated sellers after a hurricane.

And we just watched two storms go by.

Either the damage is too much to deal with… or boat owners have had enough of dealing with this year after year and they just give up.

I like to tell myself we made a shrewd business decision by boat shopping after the storms.

Or we were crazy.

Both can be true.

The Filter for a Liveaboard Boat in Florida (aka: how we tried to be responsible adults)

Once we stopped drooling and started thinking, we learned something important:

In boat world, length is money.

The longer the boat, the more you pay for a slip.

And apparently there’s a magical line where the price jumps.

For us, that line was 40 feet.

So we built our filter.

Not because we wanted to be boring.

Because we didn’t want to be broke.

Our filter looked like this:

Under 40 feet (because slip pricing is rude)
Two engines (maneuvering plus redundancy if an engine quits)
Big enough for the boys to visit (more on that delusion later)
Strong bones with character, not a floating science project
A boat we could make our own

I had piloted 30-foot boats before, but 30 wasn’t going to cut it for the life we were picturing.

We wanted something bigger.

Not huge.

Just… home base that floats.

Enter Shirley (aka: Boat Realtor, Therapist, and Translator)

We started living on Boat Trader like it was social media.

Scroll.
Dream.
Screenshot.
Send to Linda.
Repeat.

That’s when we met Shirley.

And when I say met, I mean she became our boat realtor and guide through the chaos.

She was awesome.

Also patient.

Because at the time, we didn’t exactly know what we wanted.

We knew the feeling we wanted.

We knew the life we wanted.

But boats have a lot of options, and it turns out words like beam, draft, and sea trial matter.

Shirley helped us translate dream into reality.

The 37-Footer That Taught Us What We Actually Wanted

We found a 37-footer that had what we thought we wanted.

It was a hurricane survivor.

Almost.

It had some damage and it was stuck in a marina that had been devastated.

Older girl.

Lots of teak inside.

We loved that.

And that boat did something important for us.

It taught us what we actually cared about.

Not just length. Not just price.

The real wishlist started forming:

Lots of teak inside
An aft master stateroom (captain’s quarters) with an ensuite head
A covered aft deck (that back patio life)
Two helm stations: a lower helm inside and an upper helm on the flybridge
Twin diesel engines (maneuvering plus redundancy if one quits)
Enough space to feel like a home base, not a floating hallway
And yes, Linda wanted room for the boys to visit

Spoiler alert: they never visited. But it sounded like a good idea at the time.

We were ready to move forward.

Until we hit a wall.

In boat buying, you do something called due diligence.

Think test drive, but more detailed.

You don’t just start it up and drive around the block.

You inspect.
You test.
You verify.
You take it out.

Except this boat couldn’t get out of the marina.

No sea trial.

No real due diligence.

And as much as we wanted to believe, we weren’t ready to buy a boat we couldn’t properly evaluate.

Also, she needed more work than our boat knowledge could handle at the time.

So we ended it.

Not because we quit.

Because the filter got sharper.

We walked away knowing something important:

Now we actually know what we’re looking for.

And Shirley could help us way better than before.

When Every “Good Deal” Looked Like a Heartbreak

After two hurricanes, there were a lot of damaged boats.

So many that it got discouraging.

You start to wonder if every good deal is just a fancy way of saying, “This boat is a heartbreak with an engine.”

And even when a boat looked decent, the slip it was in often wasn’t live-aboard.

A lot of marinas were gone, which caused a shortage of slips along the Gulf Coast.

And live-aboard slips? Even rarer.

So now you’re not just shopping for a boat.

You’re shopping for a place to actually live on the boat.

Totally different problem.

So we did what we do best.

We took a cruise.

Listen, cruises are our thinking place.

Cruises are where we dream big and make plans without the land yelling at us.

Now THAT is a boat.

The Condo That Didn’t Work Out (And Thank God)

Here’s the part Linda reminded me of, and it feels like a wink.

Back when we were stuck in Las Vegas, in the early “we might need a home base” phase, we were on realtor.com looking at condos on the Gulf Coast.

Not just anywhere.

Madeira Beach.

We even talked to an agent about a condo with a dock.

Then we found out most condo associations don’t allow VA loans.

So we wrote it off.

No condo. No dock. No Madeira.

Or so we thought.

The Call That Changed Everything

When we got back on land, Shirley called.

She said, “You need to come to Madeira Beach.”

That sentence is how most of our life changes begin.

A gentleman Shirley had sold a boat to, and become friends with, had passed away.

His kids lived in Iowa.

They didn’t boat.

They didn’t live here.

They just needed it gone.

Now, I’m not saying the universe, life, or God would have someone die so we could have our dream boat.

Let’s not get weird.

But I am saying this:

It was the right boat at the right time, in the right hands.

And it was priced to move.

The Boat That Broke Our Rules (And Why We Let It)

Here’s the twist.

It was bigger than what we were looking for.

44 feet.

So much for our under-40-feet plan.

But the second we stepped onboard, we realized our filter wasn’t about feet. It was about fit.

Because somehow, the boat Shirley found had every box on the list we had just earned the hard way.

Not part of it.

All of it.

It was like God had already set the table before we knew we were coming to dinner.
(You might call it the universe, life, coincidence, or whatever. I call it God.)

Lots of teak inside
An aft master stateroom (captain’s quarters) with an ensuite head
A covered aft deck (that back patio life)
Two helm stations: a lower helm inside and an upper helm on the flybridge
Twin diesel engines (maneuvering plus redundancy if one quits)
Enough space to feel like a home base, not a floating hallway
And yes, room for the boys to visit

A 1980 44’ Classic Motor Yacht with strong bones and a beautifully done interior.

It needed work, yes.

But by then we already knew the truth:

They all need work.

Madeira Was the Deal (The Boat Was the Bonus)

Then we saw where it lived.

The slip was designated live-aboard.

That is rare.

The marina was in the heart of everything Madeira Beach.

Restaurants.
Shops.
Bars.

And if you threw a rock across the street, you’d hit the beach.

You’re welcome, Linda.

This wasn’t just a boat.

This was a floating home base in exactly the kind of place we wanted to be.

And here’s the kicker.

It was three blocks from the condo we had looked at back in Vegas.

That’s not a coincidence I ignore.

The filter shifted.

Because the goal was never “own a boat under 40 feet.”

The goal was “build a life we want to live.”

This boat fit the life.

So we adjusted.

Sixty Days From Intention to Keys in Hand

It was priced to sell.

And sell it did.

To us.

It was ours within two weeks.

And here’s the part that still gets me:

We walked onto OUR boat sixty days after declaring our intention to live on a boat, float around Florida, and maybe cross over to the Bahamas.
(Read: Declaration of Intendependence™)

Sixty days.

We were excited.

We were nervous.

We were also standing there thinking:

Hell yeah. We’re doing this.

Which is usually a sign we’re doing the right thing.

There’s a saying every boat owner warns you about:

“The happiest day of a boat owner’s life is the day he buys it and the day he sells it.”

I get it.

But in that moment, stepping onto our boat for the first time, I was pretty sure we were going to be happy most of the in-between.

Life Design Takeaway

The filter is not a cage.

It’s a tool.

Our original filter said under 40 feet.

Reality handed us 44 feet.

And instead of calling that a failure, we treated it like a yes-for-now decision.

Because when the intention is clear, you can be flexible on the method.

That’s how you build a life on purpose.

Want the whole boat season in order? Start here: Life Afloat: The Boat Season

Helmets optional. Detours allowed. Autopilot disengaged.

With love and laughter,
Matt & Linda
No 2 The Quo

Want to see the boat with your own eyes?

If you’re curious, here’s the actual first walkthrough video from our very first visit. Linda gives the tour and hits all the “this is why we said yes” highlights.

Fair warning: this is the moment we stopped pretending we were “just looking.”

Want the framework behind it all? Start the Declaration of Intendependence™ series here.

Before We Had the Framework, We Had the Stories

We didn’t start No 2 The Quo with a tidy little life design model and a color-coded spreadsheet.

Shocking, I know.

We started with a few lived decisions. Big ones. Messy ones. The kind where you say, “This is probably fine,” while quietly wondering if you have lost your entire mind.

These three stories explain how we got here before we had the words Declaration of Intendependence™ to describe what we were doing.

These are the origin stories behind No 2 The Quo.

👉 Why We Said No 2 The Quo After the Kids Left Home
👉 It Took Two Years to “Suddenly” Change Our Lives
👉 Yes, We Really Did Pack Our Whole Life Into a Car and Leave

Ready to Start Redesigning Your Life?

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