Inside the Real Key West – With a Local Legend

Mar 29, 2025 2M Views 3.5K Comments

Key West has changed dramatically over recent years. Despite this reality, a strong old-school community is still preserving the local Key West culture. Join me as we meet the locals to tap into a somewhat bygone and stuck-in-time (in a good way) era.

► Visit David’s exhibition in Key West:

► Google “David Wegman Artist” to see his work

► Get Local Key West Candles:
instagram.com/keywestcandlecompany

► Book Tyler’s Fishing Charters:
peakcharters.com

► Book Olsen Adventures:
olsenadventures.com

🎵 MUSIC USED IN THE VIDEO:
► Thompson Town Flowers – Montego Sunset
► David Wegman – I’m Going to Pakistan

► 🎞️ Video Edited By: Natalia Santenello

[reggae music]
[rooster crows]
[Peter] David, quite an interesting zone
you got here.
-Yeah come on in.
This is the main house.
-Oh this is cool.
So this is like an artist’s studio here.
Yeah now we kind of rotate.
Chuck’s visiting for a week or two.
-Your buddy?
Yeah that’s his room
and this is Heidi’s room.
I stay in my studio.
-How long have you lived down here?
Key West, I’ve been over 55 years.
Here’s the galley.
This kitchen’s been…
For 40 years we haven’t changed it.
Set up, you know,
it’s just a two burner cook stove.
Nothing fancy.
Maybe a new refrigerator.
-This is your buddy, Chuck?
-My buddy Chuck here.
-Chuck keeps it together?
[Peter] So you got a good group of people
that you sort of got a commune going?
What would be the way to say it?
Not really a commune.
A group of… The thing we had in common,
we were all sailors.
We had boats.
-This is your place?
-Yeah this is the painting.
Kenny Chesney came,
he saw this painting and this is–
-Kenny Chesney? The country singer?
-Yeah.
-You painted this?
-Yeah.
-You make music too?
-Oh yeah.
-Now look under here.
-That’s beautiful.
Under here is 30 paintings.
This is all ready to hang for the show.
-You got a big show coming up?
-This is real big show.
The biggest gallery in Key West.
-Beautiful.
These are stuff I found on the street.
-On the street?
Yeah it was broken and I fixed it
and I made it look like bronze.
It’s just fiberglass.
You’re not selling this
isn’t rake art is it?
-No that’s–
-In Palm Beach there’s
an exhibit like this.
-Different kinds of rakes?
-Yeah, they’re selling.
No this is just stuff I find
like that saxophone.
-Oh yeah.
-Why leave it on the street
when I could pick it up?
That had its head broke off
and I put that back on and bronzed that.
So we’ll go cruising?
-This bike here?
-Oh yeah I can ride that.
Yeah there you go.
-You’ve had this 50 years?
-This one here.
-Okay.
-This is an old mail delivery bike.
-US Postal Service?
-Yeah.
-Really?
-Yeah.
People say why don’t you
paint it and fix it up?
What good is that gonna do?
Like I’m trying to… I want it to be shiny?
I’ve never painted it and I never will.
So that’s what they used how many years
ago?
This is probably from the ’50s.
-Sixties maybe.
-Okay.
[Peter] You’re gonna
hold down the fort?
-She’s the boss.
-Heidi’s the boss?
You keep these guys in line sort of?
She’s our den mother.
We’re pirate scouts
and she’s the pirate den mother.
I just started something.
Now I’ve got a garden.
But you’ve got to have wire
to keep the chickens out.
-Have a good ride around town, guys.
-Thank you.
So you call this place Chicken Preserve?
Yeah. Now this is how I get around.
I tell people it used to
belong to Pablo Escobar
but it’s a big fat lie.
-You’ve got some sticker bullet holes?
Yeah I put some bullet holes and they go
“Those aren’t real bullet holes.”
[laughs]
We’ll ride down to the bowels of Key West.
[David whistles cheerfully]
So you’re literally a block away
from the main tourist street huh?
Yeah, middle of town.
Halfway between Blue Heaven,
the best restaurant and the best bar…
-Which we’re going to stop up here.
Here let’s go up on the sidewalk.
This is John, he wanted to put in
where he could get an air pump right?
Like an old gas station.
On the Internet they were
like $2000 for a real one right?
I said I’ll make you one for $200.
-You made this?
-Yeah look.
The crank is just a window crank.
This is a license plate cover
from a license plate.
But it’s handy.
It rides a lot easier when…
[air hose hisses]
But um…
-Oh this is you too? Wow.
-These doors are mine.
And it was… You see over here?
This was…
Look, there’s the master himself.
This is Pete, John.
-How you doing?
Nice to meet you.
[David] He’s doing a documentary
on Key West.
-Oh nice.
-Yeah.
Certainly a big part of it right here.
-Have you lived here for a while?
-Fifty years.
How is town right now?
What’s your take on it?
I think you can’t really screw it up.
I mean it’s a beautiful place.
The people. The people are real.
When you meet the real people here
it doesn’t matter how much traffic
or anything. Right John?
No it’s still great.
-Mosquitoes… nothing.
Now there’s a big plague from termites.
They had to close down
Blue Heaven the other night
for an hour to get rid of…
Turn all the lights off.
-Yeah.
‘Cause the termites
are swarming just like…
If it ain’t a hurricane or rain
or something else… termites.
-Mother nature bats last.
[laughter]
So here’s the library. Look.
These are all…
I would go to people,
friends of mine mostly,
I would say think of a title
of a book you would write
or something that says you, right?
So these are all friends of mine.
-“There, I fixed it”.
-Yeah there’s–
-“Webster’s”.
Yeah “Dick and Jane”.
I don’t know who that was.
“Dick and Jane”.
Yeah “How to Act”.
Harry Powell was a city commissioner
and got thrown in jail
for strapping dynamite to him.
“The Last Of The Mojitos.”
[laughter]
Yeah. This is a real Key West bar.
Voted number one bar and music venue.
Yeah the Green Parrot.
-Green Parrot? Okay.
Can I poke the camera in?
-Oh God yeah.
Oh look at that. That is classic.
See all these?
These are instruments I’ve painted.
-Oh beautiful.
You’re super prolific David huh?
Well you can’t do it when you’re dead.
[jukebox music plays]
This is called
the rich and famous only bar.
Here’s Key West
in 1971 with snow on the ground.
-No way.
-And then here’s my boat
that I lost in Hurricane Irma
that I sailed around the world in.
-Around the world? Wow.
-About eight years around the world.
Here’s… John picked all
these out from my portfolio
so I made the bar and put them on here.
[Peter] It’s sort of a mix, David,
of the old world and the new world huh?
-Yeah but you know it was the underbelly
which most people don’t ever get to see.
They go to Sloppy Joe’s, Captain Tony’s,
they don’t go to the Green Parrot.
All they see is other tourists.
Right.
This is the gallery.
Where? This one?
-Around the corner here.
They own this whole building.
So that’s going to be April 3rd.
This is the county jail and courthouse.
Have you ever been in there David?
-Not that one.
-[Peter chuckling] Not that one?
Okay and I want to point out
to the audience here
right behind you,
mile zero, the famous tourist sign.
This is the start or the end
of US Route 1.
Which goes all the way up
to the Canadian border up in Maine.
And so for those of you
who don’t know the Florida Keys.
I’ll put a map here on the screen.
Tropical islands connected by one road.
And Key West, the southernmost
point of the United States.
-Yeah.
Yeah guys quite a special feel here.
There is a vibe.
There’s a, not a surprise, an island vibe.
All this old architecture,
the breeze, the banyan trees.
Guys like David
I guess are an endangered species.
I mean he’s got his posse here
and there’s a lot to get into.
The guy’s got a mega story
and he’s a character obviously.
So I just got to work into
getting that story out
while not crashing on my bike
with the garbage truck
behind me and the camera.
[Caribbean music playing]
This is Ed Swift’s, the museum.
The records museum.
-So this is the super touristy part.
-This is… right.
[David] Ah the boat’s gone.
Finally they took it away after 30 years.
-What’s that?
The boat sat right here.
It was a turn of the century sponge boat.
-Oh.
It was there two days ago.
Chickens were living in it. Termites just
ate… You know, it was a feast for them.
The end of that end of an era.
This was Howie’s Bar
right in front of that tree there.
-See where it says gallery?
-Yeah.
Coffee Butler played on weekends
who the amphitheater’s named after.
And Jimmy Buffett was playing downstairs
for 30 bucks a night.
But I lived upstairs with
my five-year-old daughter.
-Oh wow that’s cool.
I made a fruit stand for her
and it sat right there.
Okay.
And she sold $100 worth of fruit
every week.
I had to get her a business license.
-How old was she selling fruit?
-Five.
-That’s so cool.
She would go to sunset,
leave the cash register,
put the money in the cash register
and we’d go to Sunset.
-Good place to raise a kid?
Yeah it was then.
I lived nothing but in Indiana.
It all started here.
Life was pretty boring until then.
I came with friends and a bicycle.
Howie rented me…
I painted his roof.
He said I want people
to see it from the airplane.
“Howie’s Lounge, the in place.”
‘Cause the planes fly right over here.
So I said I can do that.
When I did, he gave me the upstairs
for 100 bucks a month.
54 feet long and 12 foot high letters.
You could see it from the plane.
I’m going to take you to a place.
A studio like the Chicken Preserve
only on a larger scale.
[bike brakes squeal]
[bike rattles and thuds]
This is called the dePoo
House after Susie dePoo.
Who became quite famous in her old age.
She was a designer
for Key West Hand Print Fabrics.
One of her claims to fame.
-So another zone sort of like yours?
Yeah.
-[man] Hey.
-[David] Hey.
-How you doing?
-Pretty good.
This is my friend Andy’s brother-in-law.
-How you doing sir? Peter.
-Nice to meet you.
So there’s a good group of you guys,
artists, sailors.
We all stick together.
-That’s cool.
Actually I retired when I was 22
when I moved down here.
Because I figured I was young and I could
do stuff that I wouldn’t
be able to do now.
So from 22 till I got married
which was 31, I was pretty much retired.
[David] Picasso never retired.
I wouldn’t want to do
anything else anyway.
[David] Bob Dylan never retired.
Musicians and artists don’t ever retire.
If you retire as an artist
you weren’t an artist.
You were maybe a teacher
or something like that.
A teacher is second-hand information.
So I’d never go with a school of art
or some teacher.
You want to learn to paint abstract?
Go clean Pablo Picasso’s brushes.
Then you’ll learn something.
I’d paint a boat a week
and that was enough to get by on.
It was cheap back there.
So I’d sail and get drunk
and the usual sh*t.
[Peter] Back then it was cheap down here?
Oh cheap yeah.
I think my nut was $60 a month
for my part of a boat.
[David] A beer at Howie’s
was 25 cents when I came to town.
-25 cents?
-25 cents yeah.
Mostly I think the musicians
have kind of kept the magic of the island.
When I go to Andy’s Cabana
and listen to music
it’s kind of like I went
back in time 40 years.
-Okay.
Otherwise it’s just a bunch of rich people
that got houses down here.
Nice places to eat
and all that if you can afford it.
There are some people
that want to try to preserve this.
-You need the next generation coming in
and taking the mantle eventually.
I would say, yeah.
The fellow that owns this, he can sell it
next week and make millions.
But he likes it.
I think he’ll stick with it.
[Peter] Okay so all the artists
are just renting here?
There’s another studio there.
-Okay so this style is what?
Is this old Key West style?
-Yeah there was a couple houses here.
That’s an outdoor sink.
-Oh yeah.
[David] And you see it goes down
through bamboo down to the plants.
[water trickling]
[Peter] Ten different studios here?
-Yeah ten different rooms.
Their room is their studio.
This is the galley here, another galley.
-So there are
ten different artists living here?
-Yeah ten different.
This is the living room.
And this piano
used to belong to my brother.
So my brother passed away.
And I told Andy
I’ll just leave the piano here
’cause I don’t have room for it
at the chicken preserve, so…
-So do you feel you’ve been able to
manifest the life you’ve wanted to?
Yeah.
-Do the things you wanted?
Sailed around the world.
I have five daughters,
grandkids, great-grandkids,
and old enough to still have time
and spend with them you know?
-That’s cool.
Not many people…
You know,
they’re so old, the great-grandkids.
Nah forget it.
-Are you married now or no?
No, no, no, no.
If you do anything in your life
learn to play an instrument.
[Peter chuckles]
And sing. It’s the greatest thing.
It opens a lot of doors.
When I was sailing around the world
I had a banjo, a violin, and a guitar.
-Universal language?
Yeah.
The best thing of going around the world,
meeting other people
doing what I was doing
and meeting the people that lived there.
The Natives.
And becoming friends with them you know?
I went New Zealand, you know, all over.
I went up rivers
and I really met the people, you know?
[David] Car troubles?
[man] Yeah the positive clamp
apparently wasn’t on tight enough.
-Yeah.
-How’s it going?
This is my friend Peter.
He’s doing a documentary on Key West.
-[Peter] How you doing?
-Hi Peter.
You live out here?
-Yeah sixth generation
here on the property.
-Sixth generations, that’s amazing.
How is it these days?
-It’s nice. Expensive as hell.
The tax bill was…
Well for our property on Duval also,
$90,000 for everything that we own.
-$90,000 tax bill?
Who owns the land at that point?
-We’re lucky that we get
rental income you know?
If we didn’t
then we wouldn’t be able to be here.
-Can you explain the Conch Republic?
You got the flag out there?
Back in 1982 the federal government
put a border crossing
at the top of the Keys
up in Florida City, Homestead area,
to protest they came up
with the Conch Republic.
-So people were angry
because the traffic was so bad?
The traffic and just
that they were treating us
like we weren’t part
of the United States.
So they came up with the Conch Republic
and we seceded from the union
and then surrendered back
and became part of
the United States again.
Key West seceded from the union?
For how long?
-I think it was under a minute
or something like that.
We declared our sovereignty and then
surrendered back to the United States.
So you protested
and you hang on proud to this day.
That’s cool. I see those everywhere.
-Take care. Thank you.
-You too. See ya.
[David] See ya Kenny.
[Peter] What a cool place.
And these places, do you know when
they were built? Like early 1900s?
-Yeah
-That’s beautiful.
-1860, something like that.
It was pretty wealthy.
Key West was the wealthiest city
in the United States at one time.
-You’re stating wealthiest city
in the United States at one time?
-Yeah.
-[woman] Hello, hello.
-[David laughs]
This is Peter. He’s doing an documentary.
Tamara.
-Do you live here Tamara?
-I do.
-How is it?
It’s so fabulous.
I’ve lived here for 31 years.
Whoa! Are you an artist too?
[mumbles]
[David] Con-artist.
[Peter] Oh look at that movement.
Wow a lot of flow going on.
And then my lover is on the phone.
Irish.
-Irish?
-Yeah.
[man on phone] I need
a chicken on a guitar.
He needs a chicken on his guitar.
It’s right up my alley.
I can do a gay chicken or a naked chicken.
How about a naked chicken?
Happy chicken.
[laughter]
[rooster crows]
[woman] Hi David.
-Hey how’s it going?
-Hello.
I came to get a drink of water.
It’s like a horse.
He knows where the stream is.
-Hi.
-How ya doing?
Good. How are you?
I’m making a video with David today.
Oh hi. I’m Nuvia.
-Nuvia, Peter.
Nice to meet you. This is Phillip.
-Phillip nice to meet you.
I’ll take a water. I got this, David.
It ain’t no sin to jump out of your skin
and dance around in your bones.
[Peter chuckles]
So what don’t you do David?
The more you do, the more you get.
See lookie here.
Here’s the book.
-You wrote this?
-Yeah.
-“Fifty Years of David Wade”.
Fifty years of paintings.
-Beautiful.
-Jim Harrison.
You know these are all my kids.
-Oh that’s cool.
-Channing.
St. Bart’s.
-Beautiful, David.
-That’s going to be in the show,
that painting.
-Nice.
-Zac Brown owns the original of that.
That’s St. Bart’s.
-[Nuvia] Oh David I’ve got…
-[Peter] Go for it.
-I’ve got two checks for you.
Oh checks again?
Oh I’ve got to go to the bank again?
Oh sh*t.
I know right?
You gotta go to the bank.
-Let me get them.
-[David groans]
The half model, that’s my…
And Polynesia.
And the portholes you know.
Those are good stuff.
And the pirate flags.
Those are all mine.
Two of them.
-Nuvia, do you like living in Key West?
I do.
I like it because it’s a small town
and a safe town.
-It’s safe?
-It’s safe.
Your guy’s crime is love?
Nobody gets mugged here.
Oh no. Absolutely not.
You can leave your car there
with your bags and nobody will touch it.
There’s no crime.
If anything happen,
come from other town like Miami.
[Peter] All right guys so we’re here.
And I believe this is
90, 95 miles to Cuba.
It’s actually closer
to Cuba than to Miami.
And we’re entering a whole different
world down here into the Caribbean.
[David] Now do you see this building here?
This was my brother’s.
He had first health food store.
He had a grand piano in the window.
And then there were jars and jars
full of herbs and spices.
This place has a lot of history.
In the ’80s there was a free box here.
There was a park bench here, not this one.
A free box where
it would be like the Goodwill
but just come and look
through the free box.
Okay.
And you could get clothes.
A piano in there.
One time Dr. John,
you know, from New Orleans,
came in and sat down and started playing.
Cool.
Tim rented him a piano
he played for a concert here.
But we had a watermelon
seed spitting contest.
Who could hit the fire
hydrant from this side?
-From here?
-Yeah.
That’s pretty far.
Stupid things like that.
I’ll show you. You were asking
about the Conch Republic.
Peter Anderson made that really happen.
He’s buried up here.
I don’t know how
he got his way into the…
It ain’t easy to get
into the graveyard here.
Well look at this.
It looks like a giant ice cream cone.
But it’s a conch shell.
So somehow he bought…
He went ahead of time
and bought that triangle there, right?
Which is not really big enough.
And I guess he showed him a picture
of a cement conch shell.
He had his ashes or something but…
-There you go.
Buried somewhere, I don’t know.
Me, just give me a stick of dynamite
and throw me off the back
of the boat or something.
[David whistles cheerfully]
[Peter] Oh this is cool.
A little playground and tight streets.
A lot of texture here, a lot of detail.
What do you think something like this
costs these days here?
-Probably $900,000.
-Okay.
-A little house like that.
[Peter] Yeah it’s really two worlds
right next to one another.
[bikes squeaking]
[bike bangs against porch]
-[woman] How are you?
-[David] I’m alright.
Pink rocks.
My daughter’s been doing some art.
Making your own gems, yeah.
-Yeah we are.
[Peter] You guys have
a historical home?
Yes we do.
So each one took two years to build.
So this one was 1916,
1918, 1920, 1922, and 1924.
Okay so this is sort of like
the new artists of Key West.
-Yeah I think living here
you kind of have to be a little creative.
There are a lot of jobs here
but if you don’t own a business
or you’re not an artist
you almost have to have
multiple jobs to survive.
A lot of people move here
and they think it’s Margaritaville
and it’s like glorious.
And then you get here
and you realize rents are really high.
-Right.
It’s a hard place to find, even housing.
-So David sort of grandfathered in right?
He’s been established.
He’s done his thing forever.
You have to find a unique situation
and we found ourself a unique situation.
-Okay can we go in?
-Yeah.
Well thanks for letting us in.
So this is a shotgun house.
So every room has a cross window
along with a cross door.
And then this was an addition.
We have a cross window to a door.
Usually that’s a door.
So back in the day
the house ended right here.
-Clear to the end of the house.
-You shoot a shotgun
straight through the hallway..
Oh okay. So intruder at the front
you got your shotgun here?
Okay. Okay. And it’s good for air flow.
Yeah. Great for air flow.
We moved down here eight years ago.
Seven, almost eight.
-From where?
-Tampa.
We started coming down here together
when we were about 22.
-Okay.
Every time we left we’d always leave
depressed wanting to stay, you know?
So we finally made the jump
when we were about 25.
-Never going back.
[Peter] There’s a vibe here,
is that what it is?
Oh yeah.
It’s like a special place for sure.
The only way I can describe it
is it’s like a whirlpool of energy.
And you have to know what to do with it.
‘Cause some people,
if you don’t tap into the creative
or the craftmen of the energy
you could easily slip
into drugs or alcohol.
-Because we’ve seen it.
-Okay.
It’s like there’s just
this magnetic pool that
it’s almost like you just
don’t know what to do with it.
And if you don’t use your
hands or brain for it
whether it’s writing books
or drawing or pouring candles
or driving boats or diving.
I do a lot of charters.
I take people out fishing.
-I don’t do commercial fishing.
-Oh nice.
I have a 25-foot center console.
I take people out.
Whether it’s fishing, snorkeling,
or just hanging out at the islands.
-Islands off here?
Yeah sandbars, hanging out.
Beautiful waters out here.
It is amazing how many people visit here
and never get out on the water. Ever.
Like they’ve been coming here 15 years
and have never been on the water.
-You don’t have a boat.
-I’m not. I’m just in and out.
It’s a whole nother world.
Blue Heaven’s a restaurant
but out there it’s really Blue Heaven.
It’s just endless.
You walk out
and you’re in the middle of the ocean
in the sand in two feet of water.
-No way.
-It’s beautiful.
It’s the whole reason why we live here.
Duval is great
but that out there is unreal.
It’s really cool.
-So you go out there and you’re just
walking on sandbars and turquoise water?
Crystal clear waters.
All sorts of color change
from all the waters.
That’s what we fell in love with.
Just the fishing, the diving.
-Nice.
Feels like you’re in the Caribbean
but you’re still part of America.
And this is a different…
A lot of people don’t understand
Florida’s many different things.
I was just up in Northern Florida
a couple days ago.
Totally different world.
It’s just a different vibe.
And there’s different history
in each place.
-Totally, this is more Cuban.
-Cedar Key is totally different than here.
Yeah we have a huge Cuban influence.
-Okay Cedar Key is totally different
than here culturally.
And this is more Cuban influenced?
I think so. Yeah.
-Cigars were made back in the day.
Yeah, and there’s a lot of connections
between Tampa and here.
A lot of Cuban cigar makers here,
once the cigar shops closed down
they went to Tampa in Ybor City.
So there’s a lot of people
that are from Tampa
or from here but they have family
in both places.
Today we’re pouring some candles
for Cuban Coffee Queen.
I have another order for a dive shop
that I’m working on in Key Largo.
In order for me to afford
to be here and have a two year old.
So I need to be able to work in the home
and not pay exorbitant amount of rent
for a shop on Duval.
So I wholesale my candles
to all the shops in town.
-Oh that’s cool. And this is your machine?
This is my wax melter–
This is our dinner menu.
When he has charters
it gets kind of confusing.
So I have to write down what nights
he’s out ’cause I got to get creative.
What’s the rent on a place like this
if you don’t mind me asking?
This would be closer to $3,900.
-Wow.
-Yeah.
And to find a place like this in Old Town
with parking is almost non-existent.
There’s a huge dilemma here
of vacation rentals right?
So the vacation rentals moved in.
A lot of people during the COVID era
bought houses here.
And some of those houses
were split into four or five apartments
because of Navy influence back in the day.
There was no industry here before that.
So then they started to split their
homes to be able to afford to stay here.
-Okay.
-Offering Navy men housing.
And then Key West has had
so many different identities.
So Navy came out.
Yep.
And then now we have tourism.
We have shrimping,
we have sponging, we’ve had–
-Cigars.
-Cigars.
Gold rush you know the Atocha.
Mel Fisher found a bunch of Spanish coins.
-So we had that rush.
-Okay.
Now we find ourself in tourism.
Which is great because we have
businesses that rely on it.
But it’s a double-edged sword
because we have friends,
they have three kids and they’re looking
for a three-bedroom two-bath.
that’s not more than $5,000 a month
and it doesn’t exist.
So a lot of the employees
at these restaurants,
do they live on different
keys that are cheaper?
Everybody’s complaining right now
because traffic
getting on and off Key West
is kind of insane.
And before we had these houses
that were four or five apartments
and they would live in
one-bedroom apartments downtown.
Now that COVID era happened
and those new people bought,
They are… Which I think
it shouldn’t be allowed
but they are basically turning
them into single-family homes.
So we’re losing
like four to five apartments
with every single-family home
that’s flipped.
-Right, and it’s a very small island.
-Oh, it’s two by four.
-Two by four?!
Two by four miles.
And DOT has regulated us so much
that we cannot build anymore
because in the case of
an emergency with hurricanes
we have to be able to evacuate
this amount of people.
So they have put a moratorium on building.
There’s tiers to it but unless you have
the top-tier permit to build
you cannot build.
All the empty lots you see, that’s it.
-But you love it that much?
-Oh my God.
I know it’s not Margaritaville
but the fact that I…
My daughter’s in a really good school.
Schools get a bad rep here
but my daughter is in
the best school on the island.
We bike to go to school. We pick her up.
We can go to the beach, the park,
the dentist, and the grocery store
on the way home.
-All on bike?
-All on bike.
Like I don’t really drive my car.
I even deliver my candles on my bike.
Parking’s hard to find and to get
in and out, it’s easier to go by bike.
But I think it’s like the most
walkable, bikeable city
in Florida at least. Yeah.
[David whistles cheerfully]
[Peter] You were saying
a lot of kids here.
Oh yeah.
I think we have more kids registered
in baseball and softball this year
than ever record before.
A lot of Navy kids.
We got Coast Guard.
A lot of Border Patrol now.
Definitely upped since
the last administration.
-Those guys have moved in?
-Oh yeah. Oh yeah.
And staging camps,
like up and down the Keys
’cause there was a while where
I can’t remember,
how many came
to Fort Jefferson in one day?
-Cubans?
-Yeah.
-About 500.
-In one day.
And this is like an island
that has no resources.
It’s just the fort out there
in the middle of the ocean.
They had to shut it down
because we were providing
water and food once they got here.
I mean you’re talking babies
like six months old,
no life jackets coming over.
It was wild.
We’ve had just like a month or two ago
they washed up a Cuban chug came over
in front of the airport.
Like maybe 40 people
on this tiny sailboat.
Kids, older people, young people.
And it’s kind of wild.
-So people don’t think of you
having a border issue but you do.
Oh we do. We had them come
to Southernmost Point.
They were getting off the boat
and walking on the land.
I mean we feel for them obviously.
I can’t imagine the scarcity
of supplies over there
but our hospitals were filled
with Haitian refugees.
We barely have
enough resources for ourself.
You had people that were going
up the Keys and even up to Miami
to have procedures done.
Like minor procedures
because our hospital was just full.
-Oh people here would have to go up?
Yeah. It’s interesting.
We have a huge
Haitian population too here.
They’re on Stock Island.
From what I’ve been told
it’s better living quarters than Haiti.
But to us it may not be livable.
You’ve got 5 or 6, 10,
to a trailer, a single wide.
And they’re just trying to
I think live the American dream but…
-What are they doing for work?
They are the backbone of this island.
They are your kitchen staff,
your cleaning crew, they are your–
A lot of Uber drivers.
Uber drivers, landscaping.
I think without them
we wouldn’t survive at this point.
We have a lot of foreigners here.
Eastern Europeans, Argentinians.
You go to some restaurants,
it’s a lot of wait staff,
people that work in the kitchen.
And we need them. We really do.
Yeah.
[rooster crows]
We’re taking a little break
back here at David’s pad.
Just wanted to chill for a bit.
He’s resting in there.
We’re going to get it back out
to show you more of Key West.
There’s some different elements
we haven’t shown yet.
Fair to say this small island,
there’s many different
identities here right?
-Oh yeah many different identities.
-Like what would be
the main identities do you think?
Millionaires. [chuckles]
-Millionaires? Guys like you guys?
It’s all changed in the last 20 years.
Big time.
-But then there’s this
Bahama Village right?
It’s right here. We’re actually in it.
-And that’s not millionaires?
-No.
Although it’s being encroached upon.
Have you been to Blue Heaven yet?
-We’re going there.
Yeah.
That’s right in Bahama village.
It’s an old whorehouse originally, yeah.
I think Hemingway used to have
boxing matches held there as well.
It’s a wonderful place but as you can tell
by seeing that place in Bahama village
the whole place is getting gentrified.
It’s no longer just a ghetto.
I mean there’s shops.
-It was a ghetto?
-Yeah kind of.
Is it low-income housing?
Yeah.
-And they’re–
Right across the street here
is low-income housing.
-So it’s mostly low-income
and then super wealthy?
Not much middle?
Right.
And tourists. Lots of tourists.
-And the chicken preserve.
-And the chicken preserve.
-Which is doing its own thing.
So David this is low-income housing
across the street?
Yeah.
-What’s the story with that? Do you know?
Every time that a cop car comes or an
ambulance comes
it takes somebody away.
It’s low-income housing,
you know, just what it is.
We’ll go, I call it
the darker side of town.
-The darker side of town?
-Yeah.
[Peter] Who did this mural
do you know?
[David] Rick Worth.
He’s having a tough time health-wise
fighting cancer or something like that.
Another artist bites the dust.
B.B. King came to town one day.
He played there at the American Legion.
You go in from the side
and there’s a kind of a stage there.
But they’re trying to fix it up
and make it a music venue.
These houses like that
it’s more low-income house.
About a month ago I hear
all these sirens on a Thursday night.
They couldn’t get the shutters open.
Three children burned up
and the mother and father.
-Only one child got out.
-Ugh!
-Horrible.
-An apartment fire?
Yeah government housing. Yeah.
[Peter] Okay so if someone is low-income
they can live here technically?
You’ve got to make less than
so many dollars a month.
Social security, elderly people.
-What’s that going to be?
-This is high-end housing,
part of the Navy beds.
Like condos you know.
What was this here?
This was the electric plant at one time.
But they’re trying to figure out
what to do with it.
But it’ll probably be high-income housing.
-All right then it just opens up here
to the water huh?
-A big park?
-Yeah.
This is the sub-base.
This is their biggest boat.
-That’s a beautiful boat.
-I don’t think…
It’s more of an antique now.
-And that’s Tank Island in the distance?
-Now it’s called Sunset Cay.
Oprah Winfrey,
lot of big high high-dollar houses.
-On that island out there?
Yeah.
Right next to it is Christmas Tree Island.
No buildings on it.
And it’s in lawsuit with the government.
A bunch of friends of mine live out there.
And it was where I got my first boat.
I was the only boat
anchored on the other side.
I never had to pay any dockage.
Six months,
I didn’t know anything about sailing.
My first boat,
I sailed out of here on my 25th birthday
going to the Dry Tortugas.
And I got in a… Hurricane Agnes.
And it kicked me around
the Gulf of Mexico for 10 days.
And the boat was sinking
but I kept it bailing and bailing.
Finally I found a Sandy spot.
-Okay.
Up on the West Coast of Florida.
And after the hurricane went by.
And the only Sandy spot
there was a funeral hearse parked.
And I sailed the boat right up
within 20 feet of the funeral hearse.
And there was a guy in a suit
standing next to it.
My boat stopped rocking.
It was the first time
I was on land in 10 days.
My hand was all infected.
I got really bad
and I walked up to him and I said,
“Who are you? Am I dead?
Did you come to take me away?”
[laughs]
He said, “No no my name is David Farley.
I own the Farley Funeral Home,
Venice Beach, Florida.
Welcome to Venice Beach.”
And also he’s city councilman.
He was looking at road damage.
And he couldn’t believe
that I was out sailing that boat
and survived the storm.
-Wow.
-They block the view here
but Mallory Square,
there’s a little piece
they can see the sunset.
There’s a whole thing.
People don’t want cruise ships here.
How do you feel about them?
Smaller ones,
but those cruise ship people,
they don’t spend any money.
Newlyweds and nearly deads.
[Peter chuckles]
[reggae music plays]
During COVID there was nothing
going on in Key West.
So we started doing open mic here.
Open mic, no mic.
So we don’t allow microphones.
Thursday night, this is when
it’s really happening here now.
It’s like if it’s cold
we have a fire going.
-Oh you have puppet shows?
-Yeah I made this puppet theater.
And every now and then
Richard and I will do a puppet show.
And those are my pirate flags I make.
What are you drawing?
This is one of the best
musicians in Key West.
[man laughs heartily]
Whoa!
[laughter]
When did you do that?
I did it today.
Whoa, out of your head?
No, no, Bill Cliff took a photo of you.
[laughter]
You nailed it man.
You even got it.
I got the shirt.
-Yeah.
-[laughter]
[Peter] No top buttons.
He’s a songwriter though that makes…
You know…
I crack up when I hear a funny song.
I mean I got songs.
“I’m going to Pakistan” you know?
But I gave you a tape of that.
You’ll hear it.
But he’s got some really good ones.
I toured for years which was great.
And then I stayed in New York
making a living playing.
And now he’s sketching.
Yeah I started drawing last year.
This town, it’s not big enough
for both of us.
[laughter]
Well I’m leaving soon.
[Peter] Do you find–
He’s doing t-shirt designs.
There goes that market.
No no no.
Is it yin and yang
going from here to New York?
Having both makes both better right?
Yeah they’re the opposite.
Everything that’s good about there
is bad about here and vice versa.
So it’s convenient,
it’s beautiful, and it’s safe and warm.
And then at night there’s not much to do.
I mean you can watch some bands
but it’s the same places.
In New York it’s just endless.
You’re anonymous in New York
and here you’re not.
But there’s more community here
which I like.
So I like both.
Actually it took me living here
to really appreciate New York a lot
’cause I traveled a lot and I was
always angry every time I came back.
But I was able to see this place
for the good and the bad
and same with New York.
[Latin music playing]
[Peter] Fresh coconuts?
Where are these from?
-[man] Key West
-Nice.
[David] That’s the best milk.
Where are you selling these? Restaurants?
I’ll just cut them open
and just get the water.
-For yourself?
-Yeah, yeah.
How much? I’ll buy one.
-Yeah, I’ll take one.
-Whatever, just, you know…
You ever have a coconut?
[Peter] Oh yeah.
How long does it take you to cut it?
-I don’t have my machete.
-You don’t have your machete?
I might have one.
Alex might have one upstairs.
Probably rusty, dull.
-It probably is.
Just grab you a couple,
you can cut it whenever you ready.
Thank you. What’s your shirt here?
Key West Conchs.
-Are you guys good?
Not so much this year but they alright.
-They compete.
-They’re giving it.
-They can only get better.
-See you guys. Thank you.
[Peter] Okay famous Blue Heaven.
So this is your friend’s place?
-Yeah yeah.
[rooster crows]
Everybody is the director
of their own movie.
And if you make a sh*tty movie
it’s because you had a sh*tty cast
and set director.
-DP was off?
Yeah you know when to say,
“cut” and “roll ’em”.
And…
-When have you said cut?
My movie is still rolling.
I’ll say cut when it goes,
[groans] Cut!
[Peter chuckling] All right
now look at that.
Is that how it is?
This is what Oprah Winfrey
came all the way down here
and probably she bought a house
down here on Sunset Key over there
’cause she came to Key West
to try Richard’s Key Lime Pie.
-Okay this is Richard’s Key Lime Pie.
-It’s famous on the island?
-Yeah.
-[bartender] Unfortunately–
-Here’s the story.
Kenny Chesney comes
and he likes the pie right?
Okay.
So he says
I’m going to bring my grandmother.
It was his mother or grandmother?
She’s like really old.
In his jet plane.
The plane takes off
and she’s flying over the water
and she’s amazed
how crystal clear the water is
coming down here.
And then she says, “Kenny can you
tell the pilot to slow down a little?”
She was amazed how fast
everything was going by
and she wanted to see the water.
So he landed and he brought her here
and she had the Key Lime Pie.
He’s on Oprah Winfrey, Kenny is,
and he’s telling her that story.
She has the mother on television
with the Key Lime Pie.
-They sent for it or something.
-Okay.
What’s going on on top here?
That’s how it got really famous,
Richard’s.
The brown on top?
-They have a way to…
-To brown it?
To brown it like that yeah.
And then it’s Key Lime is 75% meringue.
Yeah on that one.
They make them… That’s not very high
compared to some of them.
-This is good. You don’t want some?
-I’ll try it.
-Can I have another fork?
-Yes of course.
But that’s the story how it really put
the Key Lime Pie here on the map.
-Oh really? That’s the origin story?
-Kenny’s mother or grandmother.
You guys make it here I hope?
-Yeah it’s made in the house.
-Cool.
That would have killed the story.
-Bakery’s on the lower level.
-This is good. This is legit.
-They bake the bread and everything.
[bartender] Oh I didn’t even realize.
[birds chirping]
[David] Tomorrow night is the fundraiser
for studios at Richard’s house.
-This is Richard’s house?
-Yeah.
Sixty people have paid $225 a piece.
We’re making it look like Moulin Rouge.
You’ll see it here.
-Oh yeah that’s cool.
-Like in Paris?
-Yeah.
You’re going to have topless ladies?
As the night goes…
If Channing has her way.
She’s the musician that’s playing.
If she has enough wine
she’ll be in the pool.
[Peter chuckles]
So did you make this
mechanical device here?
-Everything.
-Everything?
[man] David,
the man, the myth, the legend.
I’m heading to your
home town of Saint Barts.
-You are?
-Today yeah.
-What’s up man?
-Peter.
-I’m Blake.
-Nice to meet you.
You can film anything you want.
Alright man thanks.
Okay so you’re
a world-class kite boarder?
Yeah that’s my job.
That’s your full-time gig?
Kiting around the world, traveling,
having fun with people
is the most important.
And I do this too, e-foiling.
Oh nice.
So this is like a battery-powered
electric hydrofoil surfboard.
And it has a computer and then Bluetooth.
It powers up the mic here.
Richard is like the e-foil cowboy.
-Okay alright.
I bought this honeybee for Dave.
We’re going to shoot champagne corks
at it for the big party tomorrow.
-You guys are pretty excited
for this party?
I am. He’s got to go to Saint Barts.
I’m excited about it.
We’ve gotten it all set up, everything,
and I’m ready but I’m leaving right now.
-Did you grow up here?
I grew up in Saudi Arabia.
-No way!
-Yeah
And then I lived in Abu Dhabi as well
and Qatar and then moved to Michigan.
Drove down here just to kitesurf.
So I lived in Khamis Mushait
in the Abha Mountain region.
Which is like
the Bin Laden family’s hometown.
-Near Yemen?
Right on the border of Yemen.
And so we lived on a US airbase
in Osama Bin Laden’s hometown
during 9/11.
-Wow!
How wild was that, those times over there?
For me as a kid
I just didn’t think anything of it.
It’s kind of like
if you’re a kid in the US you know?
It happens and your parents are sad.
You hear about it it’s very sad
but we didn’t feel in danger at all.
-Is your dad in oil?
Is that why you’re over there?
School teachers, my mom and dad.
-Oh cool.
Yeah, so…
-I love Saudi. I find it to be
very hospitable, safe, good to travel.
It’s beautiful too.
-It’s beautiful. That area is beautiful.
People don’t think
Saudi Arabia and cool weather.
It’s like misty and cool.
It’s like San Francisco weather.
I would say that if anyone were to go
visit Saudi, I would say go to Jeddah.
Yeah it’s interesting.
I mean I grew up in Jubail
in the Persian Gulf
which is beautiful
but it’s more like straight desert.
The red Sea side is just so beautiful
and it’s like mountains
straight to the sea there.
So how is it living in America
after growing up in the Middle East?
It was quite shocking.
After 9-11 we moved to Abu Dhabi.
Okay.
You move to America
and you think oh it’s a free country
but we could actually do kind of anything
we wanted adventure-wise with Ekeli.
In Saudi you could just camp anywhere.
You could go and surf on the beach.
You could climb mountains do whatever.
Less regulation.
Whereas there’s a lot of regulations
when you came here.
So there’s a lot more freedom.
I’m a man.
So as a woman you’re really restricted.
-Yeah.
My mom would go out
she’d wear a black kabaya, everything.
And we were lucky ’cause we’re
just fortunate to be Americans.
That’s how we grew up.
So they treated you well?
Kind of a golden passport where
you’re allowed to do whatever you want.
Right, you’re not expected
to be Saudi obviously.
No but if I just was born
in a different country
then it would be a different situation
for that type of thing.
-Or the color of my skin.
-Right.
In the US there’s lots of minorities.
I was a minority there because I’m the
only blonde-haired White person around.
[chuckles]
All my neighbors were Saudi and then
I’m a blonde-haired, blue-eyed person.
It was really cool.
I love it over there.
-And then do you love Key West?
I love Key West.
I’ve lived here for 12 years.
I go on vacations with people
and it’s the full-time thing.
I send other people
on vacations with other people.
Okay.
Because you live your life
and the most valuable thing
in your entire life
that you realize is your time.
Yeah.
And every day
and every minute of like right now,
the way that you spend your time
is the most important thing of all.
You have very wealthy people in the world
and they’ve worked so hard
to make that happen.
So once you reach
a certain point you’re like,
“You know,
I need to enjoy all of my time
and I need to have the most fun
that is humanly possible
and do what makes me really happy
with my friends and my family.”
And so that’s what we do
is help people do that.
-Okay so you’re going on a vacation
with people that hired you
to come out and show them
the way basically?
Show them kiteboarding
or whatever adventure?
-That’s it yeah.
-Okay cool.
I have me, but then also a team
of people around the world
and you select what you want to do.
-And where you want to do it.
-That’s interesting.
And then we help you find the people there
or send people from anywhere in the world
specifically to help
you have the most fun,
be safe,
learn new sports and tricks or anything.
Anything that you ever want to do
and anywhere in the world
you want to do it,
that’s what I do is Olson Adventures.
-Olson Adventures?
Blake Olson.
-Okay do you notice with all your clients,
what do you think they’re missing out?
Everyone thinks you have
the most money right?
Then you got everything figured out?
And life is just great.
And that’s a goal for many people right?
Just to have a big number and then
once you get there all is good.
Is that what you see or what do you see?
No.
Because it could be a never-ending
number that you’ll never reach.
At a certain point you realize,
“Oh I’ve wasted a lot of time doing
something that I don’t need to do.”
-Right but it’s a balance right?
You need enough numbers
in the account so you can do things.
That’s it.
Right you need that balance
and dialing that in.
Yeah and some of my
favorite people in the world
are like the Bedouin tribes
that are super happy
and live in a tent
in the middle of nowhere.
They’re nomadic and have
very little but connected.
You know…
I lived in Vietnam for a while.
My neighbors didn’t have much
but their community.
-Yeah.
-Yeah. So you know?
Oh go ahead.
Here Gabby.
Oh I didn’t want to interrupt you.
-Oh that’s all right.
Gabrielle what are you up to?
Are you part of this event?
No I’m Richard and Blake’s roommate.
Oh yeah?
Yeah and I’m going…
I just worked at Blue Heaven this morning.
And you’re styling.
Yeah.
-Super stylin’.
-Always always.
Well if I have to work
I want to look nice.
I’m really really tired.
And I’m like if I wear an outfit like this
nobody’s going to look in my face.
-How long have you lived here, Key West?
Well I lived in Key West
from ’91 to 2016.
And I live in Germany now.
-Okay.
-But I’m here for six months.
-Oh cool.
And I worked at Blue Heaven since ’94 so…
-[German]
It’s my family.
-Oh nice.
So I’m going back there.
-How does it feel to be back in Key West?
-Awesome.
-Awesome?
-Awesome. I love it.
I couldn’t live if I couldn’t
come to Key West once a year.
It’s my home.
-How do you… This is a long conversation
but the differences between the vibe,
the feel of Germany versus the US.
Oh my gosh.
It’s incredible.
I mean but Key West
is not really the US you know.
-It’s doing its own thing?
-Key West is its own thing.
It’s people just… I don’t know.
Friendlier and more open.
And you know everybody
talks to each other.
Even I started it in Germany.
I work in a bookstore
and I always say I’m an American
with a German passport.
I’m more American than German.
-I don’t feel German at all.
-Wow.
So I’m really thankful
that I can stay with Richard.
-Cool.
I love working at Blue Heaven.
-That’s where I’m going now.
-That’s Richard’s restaurant?
-Yes.
-Okay.
All right
well it was nice to meet you Peter.
-Nice to meet you.
All the best Gabby.
[woman] Wow.
So it doesn’t turn, does it?
Yes it turns.
-The wind will turn it.
-Oh the wind will turn it?
-It’s well balanced.
As a French Native
do you approve of this?
Oh my gosh, it’s wonderful.
Yeah we just need to have
a sex shop next to it. That’s it.
-Sex shop?
-Well Channing’s coming.
Yeah I know but we need
some little sex shop booth.
You know
that’s what Pigalle is all about.
-Do you live here?
-Yeah for 45 years.
Wow.
I go to France every
three months right now.
I used to have the business
across the street from Blue Heaven.
I’ve been commuting for 45 years
and this is where I’m in my life
and I love Key West.
I will not live anywhere else,
that’s for sure.
-Other than Key West?
Beside Key West, no.
I met my husband in Key West
and this is where I want to be.
-One person get right there.
-I’m right there.
Watch your window, Zane.
-Watch out there, Richard.
-All right don’t lift so high.
Don’t lift so high.
You don’t have to go… just off the ground.
All right should we sing a French…
What’s the French national anthem?
[all singing “La Marseillaise”]
[David sings Frere Jacques]
[singing and laughing]
[woman] Ooh la la.
-[David] All right.
-[Peter] Moment of truth.
-Lower your hands.
-All right lower the bottom.
Pay attention. Pay attention here.
All right come on.
[woman] This one is down on the way.
Wow! This is so awesome.
Let’s go on up.
Right up tight against the door.
You got some rope?
Chop chop.
[French burlesque music plays]
[David] Come on this way.
Can you make me a Moulin Rouge?
Sure Richard, no problem.
This is the other piece.
[Peter] Oh cool.
-Cafe de Richard.
[music continues]
The Moulin Rouge.
Oh the chicken preserve.
-Where? Who are these people?
-[giggling]
-One thing starts another thing,
you said off-camera.
One thing starts another thing.
It’s what people do in Key West.
Richard is doing this totally for free.
-Yeah.
-He’s not getting anything out of it.
Well thank you
for showing us that community.
-Dabbling in today was cool.
-You got a good look at it.
Yeah. All right.
Anything else you want to say?
Into the camera.
There you go.
Love many, trust few,
but always paddle your own canoe.
I like that.
That was in my last book.
Beautiful.
My new book coming out soon,
“In the wake of a dream”.
Do you have a website?
Yeah. If you Google David Wegman
a lot of stuff comes.
I had no idea you were so prolific
and did so many things.
But that was very interesting.
Like I say, you’re the director
of your own movie.
And if you have a sh*tty movie
it’s because you’re a sh*tty director.
[Peter chuckles]
All right guys. Thanks for coming along
on that journey.
Until the next one.
[accordion playing]
[David voiceover]
The world is full of so much hatred.
Wouldn’t it be nice
instead of dropping all the bombs
we could just drop like small accordions
or little guitars
with sheet music over Iraq.
And the little kids would find them laying
on the ground and start playing music.
[music continues]
Or maybe I could just go over there.
Pakistan, start there.
And form my own band.
[music changes to bright banjo playing]
♪ I’m going to Pakistan ♪
♪ I’m going to form a band ♪
♪ Play mu’ to Taliban ♪
♪ That’s where I’m going ♪
♪ It’s always sunny there ♪
♪ I’ll never have no care. ♪
♪ Pakistan, I call it home ♪
♪ They may have earthquakes and snakes ♪
♪ And fundamental Muslim ♪
♪ Monsoons in July ♪
♪ Oh typhoid and floods ♪
♪ And rare amoebic dysentery ♪
♪ But I’m going to try ♪
[banjo music continues]

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