Solo Road Trip to Key West! Big mistake, but then...

Motorcycle Adventure Tour
12 followers
8 Video Views·Jun 18, 2025
A 2000 mile road trip, ALONE, on a borrowed Harley Road King, to KEY WEST. This time, I ride the MOST SCENIC roads such as Seven Mile Bridge, Ozello Trail, A1A, Tamiami Trail in the Everglades, and more. I visit @shadetreesurgeon, @UncleBogator and@BlockheadMoto. What's a road trip without broken itineraries, lost items, near heat stroke, and the feeling you get when it's just you, two wheels, and the road.
I planned a 2,000 mile road trip alone to Key West.
This is the bike I borrowed for the trip,
Scarlett O'Harley, a 2021 Road King.
30 pounds lighter than the last two bikes I rode,
but still about 400 pounds heavier than my own bike.
Taking notes for my first two trips
and reading your suggestions in the comment section,
I tried to make this trip
how I should have done the first two.
Instead of 12 hour highway rides for days in a row,
this time, I'd take scenic routes,
including the famous Everglades Roads,
Seven Mile Bridge, and A1A,
which you can see more in another video
or in my digital Florida travel guide.
And this time, I'd actually stop and enjoy some sights.
Doing a trip this way, it changed everything for me.
I saw some of you commented on my last road trip videos.
Why am I riding such big bikes?
And why not just take my own bike?
I'm glad you asked.
For me, that feeling of overcoming a challenge,
any challenge, is addicting.
I once struggled just to take these bikes off the kickstand.
And I used to think I couldn't handle bigger bikes.
But now that I've learned how to handle them
and realized how simple it is,
I've gotten hooked on bikes that insecure guys say
I shouldn't be riding.
And to those who say that riding a bike
that's too big for you is dangerous,
that is when I refer to those
who I actually know and trust,
like Jerry Palladino,
a five foot, seven inch tall retired cop
that has taught me and thousands of other smaller riders
how to handle 800 pound bikes.
A lot of people think that size or strength matters
when it comes to motorcycling.
Well, in a lot of sports,
whether it be boxing or wrestling or weightlifting,
size or strength may matter.
But in motorcycling, it clearly does not.
It's all technique.
And why not just take my own bike?
I'm interested in getting a more long trip friendly bike.
And I think the best way for me to learn
about those kinds of bikes
is to ride as many of them as I can.
Might as well do it on an actual trip.
Thanks to you all watching, my patrons,
channel members, and those buying off my store,
making videos out about motorcycles is my job now.
And the neat thing is,
it's pretty much up to you and me what those videos are
and what my work days look like.
So I planned a 2000 mile route
going down Florida on the West side,
coming back on the East side,
visiting friends on each side,
taking plenty of scenic routes
on a bike that is perfect
for the long flat stretches of Florida
and packing up like a mule.
As for the name, Scarlett O'Harley,
I didn't make that up, one of you did.
Y'all are a lot better than me
at coming up with good names for bikes.
One of you emailed me right after the kickoff video
for this trip,
just a little bit further from my original route
was the southernmost point of the continental US.
So I added one more stop to the route.
Thanks, Ernest.
I also saw some of you commented,
why do these trips alone?
Isn't it safer and more fun to do trips with others?
Why not bring a friend or my husband along?
Well, thanks to you, this is my job.
I can leave for two weeks with little notice
and technically continue working.
Thankfully, my new admin helps with that too.
My husband has a nine to five job.
It's not as easy for him to leave on short notice
for weeks at a time.
And as far as inviting a friend,
I actually really like riding alone.
Being able to ride at your own pace,
take the breaks and detours you want when you want them,
not having to worry about slowing someone down
or speeding them up,
or even just dealing with the tension
that can sometimes happen
when people are together for too many days in a row,
I find the solo rides very peaceful.
But that doesn't mean I'll never say no
to riding with others.
Like a group ride with the Shade Tree Army.
Hey Mike, look at that bobber.
Look at you looking all hipster.
He has a long beard now.
Yeah.
Hello.
Look at that beautiful man.
I'm just kidding.
How are you doing?
Gorgeous queen.
How you doing baby?
Good, how are you?
What's going on?
Amazing, thank you for asking.
If I was any better, I'd be twins.
Dude, you see this thing they sent me?
You ever ******* get these people
trying to send you these things?
All the time.
I ******* finally took one.
Yeah?
How is it?
I don't know.
Did you make a video on it?
Did they tell you to make a video on it?
Yeah.
Is that what that's supposed to be?
You're not gonna do the video?
What are they gonna do, sue me?
You're a bad boy.
I'm gonna make a video on it.
So I'm gonna try to take it camping,
maybe like 30 miles away,
like really at the edge of its range.
Probably gonna die.
Why wouldn't you be able to do it though?
I mean, it goes at the ******* speed limit.
They always tell you more than it actually can go, I think.
Whoa.
Hey, speaking of no helmet,
this one was on the Royal Enfield in shorts,
evening shoes, no helmet.
You bad bitch.
I didn't put it on YouTube for a reason.
What you dropping all this money for?
Jasmine, taking pictures of everybody.
I hate cash.
You hate cash?
Yeah, for a reason.
Mike, you just dropped another dollar.
See what I mean?
Well, maybe you need a money clip or something.
Oh my God.
You crazy?
There's Mike and Jasmine, Mike Branch Rides,
Courtney and Shade Tree,
Brant,
and me on the road camp.
Woo.
Hang it in, have it in.
This is the coolest place I've ever seen.
Look, there's motorcycle education.
There's parking for bikes.
You can pull right in here.
There's the bar, dance, Shade Tree, Courtney, bar stuff.
And then when you park here, you can just roll right out.
And then the dealership right there.
What?
Next, we were heading over to the famous Dirty Shane.
You see the oddest things in Ybor City.
It's an all wheeler?
This painting, this famous painting.
Where did it go?
Okay.
We got you covered.
Wow.
Right in there.
Show us what you're working with.
What is this?
Oh my God.
No.
Come on, take a spin.
No, oh, okay.
I closed the thing on though.
Oh, there's mirrors.
Oh yeah, of course there's mirrors.
It spins.
Yeah, makes it easier.
Okay.
You ready?
Oh my gosh, you're a natural.
I'm difficult.
You ready?
Okay, hold on.
One, two, three, you got it.
Look at you go.
Woo.
There you go, my gosh, dude.
I'm about to spend every single dollar I got.
Oh my gosh.
You dizzy?
Oh, yeah.
Doodle, I've almost never meet my match,
but I've met my match here.
Some people are just so good.
You can't corrupt them to the dark side,
but the fun's in trying, baby.
Fun's in trying.
Oh my gosh.
Next would be the last scenic road before the Keys,
the Tamiami Trails through the Everglades.
We're here.
Ta-Miami, Ta-Miami Trail.
Looks like I'm not alone.
French family, or couples.
Who do French like Harley?
I continued my slow sightseeing route down south
and kept running into the problems of high season,
which apparently starts in Florida in late February.
You're sold out.
Okay, thanks.
My Airbnb lady just messaged me now saying,
had a last minute emergency and is hospitalized.
Yes.
Hi, do you have availability for one bedroom tonight?
All right, thanks.
So I found one hotel maybe,
but they won't reserve over the phone, which is stupid.
I'm like, you can take my money and I won't reserve it.
It's first come, first serve.
So I'm going there now.
Sun is like already about to set.
My friend.
Whoa.
Okay.
Look like I just beat the rain at least.
Well, that was good luck.
I am all fresh and clean
after being all hot and sticky and stinky.
I am only three hours away
from the southernmost point of the continental US now.
It's six in the morning.
I hope this engine only wakes up
the girl that woke me up around two in the morning
banging on the door for her mom to let her in
and nobody else.
Hello.
Do y'all have coffee?
Coffee?
Gracias.
Oh, yes.
I don't drink coffee often,
but since I woke up at two in the morning,
thanks to my lovely neighbor.
Let me just make sure this isn't the last gas station.
Oh, there's plenty of gas stations until the end of US.
I'm fine.
104 miles to go.
Ooh, gonna love this.
You'll be, girl.
Will you stop rubbing that in my face?
I'm not gonna.
I usually ride in silence,
but this trip, I actually listened to some music
and I was surprised.
I really liked it.
When my ears start hurting, I just switch earplugs.
I was just using these foamies.
Now I'm gonna use these loops.
This Florida humidity, it's not even that hot yet.
And I've gone 50 miles
and I've already stopped two times.
Maybe even three.
Oh, boy.
But 51 miles until the southernmost point of the US.
By and coconut water.
Which one should I get?
Should have gotten coconut water.
Uh-oh.
My plan was to start early in the morning,
make it to the southernmost point of the US by midday,
and turn around and start a journey back up north.
I didn't know that I was about to run into problems
that derailed that plan.
This is not turning on.
This red light is flashing.
Enter pin.
Oh, no.
Oh, I can't be serious.
I actually lost my key fob
wherever I am at at this gas station.
I know it's here because I got here,
but I can't leave now.
Oh.
Oh, so it could be at my last stop.
Shit.
Oh, no.
Oh, okay.
I'll find out what that is.
Does this have a different key?
Hello?
Can I leave a key fob, a Harley-Davidson key fob?
We have a key fob.
It's at a shell an hour away.
So I can take an Uber for $100.
I mean, worst case, I could hitchhike or Uber off.
We're five minutes up the road,
so if you need to call me,
I'm home for the rest of the day.
Thank you so much.
Okay, thank you.
Thank you.
Hi, Alexis, this is Carolyn with the Road King.
Oh, absolutely.
Can you be okay with me?
Hi.
I don't know what it is about the keys.
Oh, dog.
No, no, no, no, don't do that.
Don't, don't, don't.
Yeah.
Oh my gosh, he's so big.
Damn.
Oh my gosh.
Thank you.
You're welcome.
Thank you so much.
I've got it.
I got my keys.
There it goes.
Damsel in shining armor.
Yeah, I don't know if I would've done that
if she had been a guy,
but definitely would've been a lot more hesitant.
Took a picture of her license and sent it to Cody,
just to be safe.
I am 10 miles away from the southernmost point of the U.S.
Oh my God.
Okay, I'm 23 minutes away.
Oh my gosh, southernmost point of the U.S.
By motorcycle and a million people in line to take a picture.
Damn it.
I just parked.
Now I'm walking to the southernmost point
of the continental U.S.
Man, there's just a thing as a cold jacuzzi
because I would love that right now.
Look, monks.
Is that disrespectful?
Once I realized I would have to spend the night
in the Keys anyways,
I decided I'd come back to the southernmost point
in the morning when I could really enjoy it
with less people around
and not fear passing out from heat stroke.
So I am no longer about to pass out of heat stroke
or dripping sweat.
That cafe didn't have AC,
but just being in some shade,
I drank two glasses full of ice water.
I never drink water with ice, it's too cold for me.
But today, it was just what I needed.
It's just way too hot to ride right now.
I'm like gonna die.
I booked a place here in Key West tonight,
really close by.
So, which I really didn't want to book a place here
in Key West because they're just so expensive,
but it's just not safe for me to keep going.
And Alexis was telling me that in one of the spots,
Islamadora or something,
it is bumper to bumper for like an hour
and you move like three miles around this time of day.
So by the time it clears up, it's gonna be dark
and I just don't want to ride in it.
I guess that means I'm forced to just enjoy myself
in town instead of just ride in and out,
which probably wasn't a good idea anyway.
So I guess it worked out.
The Key's humidity was really taking a lot out of me.
It wasn't until hours later that it dawned on me.
I didn't even go in the water.
That made me realize how unclearly I was thinking.
AC has never felt so good.
What a cute little room.
Nothing like putting on food
you were sweating in the day before.
Okay, we're here and there's not a big line.
Can I take a picture with you?
Sure.
All right, cool.
Are you hot?
Cause I'm so hot already.
Yeah.
Oh my gosh.
We came down from North Carolina
and we started out with heated gear
and we ended up with like this.
I'm already sweating.
I'm like, it's low 70.
The answer is humidity.
Yeah, it's crazy.
It's too hot.
It's too hot down here.
I'm ready to go back up North.
Nice to meet you.
Have a safe ride back, all right?
Thanks, you too.
All right, have fun.
That might be the first time that's happened
not at a motorcycle specific event.
So I started up North out of the humidity
as fast as I could.
And it turned out to be a good thing I did.
Luckily, what I missed in the Key's,
I'd be able to see in my old stomping grounds
further up A1A.
Unlike my first trip,
the rain clouds seem to stay at bay the whole trip.
Either never in sight or just out of my reach.
You ladies call it.
Hello.
How are you?
How are you, girl?
Hold your breath, I might stink.
I've been sweating for two days.
Can I just go straight into the shower?
Yes.
And then I'll do laundry?
Just make sure it's nice.
Oh.
Okay.
I can hear Jimmy Buffett.
I'd, oh!
I need a, I should probably take that actually.
It's broken.
How are you?
Good.
Good to see you.
Thank you for letting me stop by.
I'm in Block Shop.
Here's Justin, video editor and multi-purpose person.
And Chris, he fixes things.
Yep.
Gonna be working on this here in a little bit.
So you guys haven't done the like grand opening yet,
but you are open for business basically.
We are open for business, yeah.
They can go to blockheadgarage.com.
Yeah, and we pretty much do everything.
So, oil changes to full frame up custom builds.
We don't really wanna do oil changes.
He's a little more qualified.
I don't think I'm above it,
but at the same time, I don't wanna do it.
What do you wanna do?
Something bigger, more badass.
This is fun stuff.
So this one's getting redone.
It's like military.
Yeah, it's gonna be OG, like a army green
with like black star, black flag.
Oh, cool.
I'm just trying to stay behind you, so.
I know, no accidental face reveals this time.
About to do a video on this one for the external breather.
So you can basically like externally vent the bike
for $12 versus a bunch of these companies
are trying to charge like 300 plus.
Oh.
Just got fishtails put onto that.
Where's the ground?
Goldie blocks.
Oh, that's good.
Yeah, right?
Justin's in the front.
He named his Ariana Grande.
Okay.
And everybody put knobby tires on there,
so it makes it fun to like go over.
Wheel and tire machine.
Waiting on my grandpa to get up here
so I can start working on that with him.
Aw.
My foot's been kind of bothering me today.
And then I looked down
and saw something really disgusting.
You wanna see?
Like, what is that?
It's like a double blister.
Luckily, what I missed in the Keys,
I'd be able to see in my old stomping grounds
further up A1A.
I had come here before as a volunteer
with the Georgia Aquarium,
aiding in their conservation efforts for right whales,
but haven't had time to be a volunteer for years.
So it felt good to at least be able to pop in
and see the animals.
Just a disclaimer,
all the dolphins at Marineland were born in human care.
And as you can see, exhibit signs of a healthy life,
like not losing their sense of play.
A life in human care is not something
I would support for all animals,
especially those born in the wild
or showing signs of distress in that environment.
But for the animals that do well in it,
it's a great way in getting people caring
and helping to protect their wild equivalents
and the environment they live in.
As a self-proclaimed minimalist,
I don't buy souvenirs unless I can eat or drink them.
But when one of the staff members
saw me eyeing the tiger shark exhibit
for about as long as the average visitor
would probably walk the whole Marineland,
he gave me this.
He said they fall off frequently in feeding,
but rarely so whole and white.
It's one of my favorite things I've ever gotten on a trip.
And the thanks to one of you
that reminded me to check the oil levels on Scarlet.
2,000 miles in Florida humidity
can really take a toll on an engine.
Luckily, Harley dealership is never far
from the road here in the US.
And Tifton Harley topped me off as I passed by,
even though I only gave them an hour's notice.
Thank you so much for squeezing me in last minute.
For me, it's not about leaving everything behind
and traveling full-time,
but adding adventures around the simple everyday life.
Family, our businesses,
being a homebody with those I love,
where my life feels the most full.
Although I do love watching those full-time motor travelers.
The next trip is the one I'm most excited about.
Less than a month away.
And I'll be on a very different kind of bike.
Click right over here for another road trip video.
