Sleeping Outside With Homeless Friends In Florida

in travelfeed •  5 months ago

“I’m with 3 Ukranian girls and we’re driving down to Florida. We need somewhere to stay tonight. Can we stay at your place?” my friend Chris asked me over the phone. Yes, the same Chris that I got lost in the jungle with!

“I guess? I just had to move back in with my parents for a little while, though. I don't have my own place anymore, so I need to find out if it’s okay. When do you think you’ll be here?”- I asked.

“In about two hours.”- he replied.

'Haha oh my gosh, he WOULD call last minute on a long road trip and ask to stay with me' I thought to myself while smiling because I love my crazy friends and the spontaneity of life.

I had to fib a little and tell my mom that my friends needed a place to stay, when let’s be honest…

... I only knew my friend Chris.

But hey, I was a couchsurfer and couch surfers are all about the hospitality and staying with strangers!

(Couchsurfing is a website where you can find people to stay with for free while you’re traveling. Some communities are super active!)

So that night, I had 4 last-minute guests at my parent's house. 2 stayed in the guest room, and I gave up my bed for the other 2 and slept on the couch.

The next morning they were all packing up the car to leave and one of the girls said “Hey, we have an extra seat in our car still. Do you want to come with us??”

It just so happens that I had JUST come back from Europe and traveling on this trip in Germany after quitting my job as a Spanish teacher, so I had some time off of work.

I actually had a new job lined up, but I called my future boss real quick to see if I had at least a week before I was going to start.

He said yes, so literally 5 minutes later, I had stuffed a school-size backpack full of clothes for the week and that was it!

I joined in on the unexpected road trip to Florida!!!

I was out of a job and my friends didn’t really have a lot of money. So, on the way down to Miami, my job was to frantically put in requests on couch surfing to see if anyone would last minute host FIVE people to stay at their house.

Honestly that was an insane request to ask a stranger.

It’s kind of a ridiculous thing to even ask of a friend, honestly. But I did it anyway.

I messaged person after person…and would you believe someone in Fort Lauderdale said YES?!?

They let us stay at their place for 3 nights!!!

They said they had just traveled around Europe for an entire year because of couch surfing. They were able to stretch their budget to avoid paying for hotels, and now that they were back home, they wanted to pay-it-forward.

Wow, we had the most AMAZING time with these 2 girls who hosted us for 3 nights.

Here we are, just randomly staying with some strangers and NOT feeling stranger danger AT ALL:

After we left the Miami area to go to the Florida keys….we didn’t have much luck with couch surfing.

By that I mean we had zero luck and we had to get REALLY creative with places to stay.

Our first night, we met some “homeless people” about our age. No worries, they let us know that they were homeless by choice and they were perfectly happy with their lives.

I don’t remember how we met, but I remember we ended up hanging out with them a lot our first couple of days there.

They showed us a secret rooftop of a business that they would sleep on after it closed up for the night. They’d get off the roof early in the morning before they opened up.

So we spent one night sleeping up there in a huge group of about 10 people.

Here are some of us hanging out earlier on in the night. The cool thing about the homeless friends is they were experts at climbing the trees like monkeys and getting down coconuts! I kid you not.


And that’s what makes this song that we listened to on repeat on the way to Florida so fitting:

Charlie Winston - Like A Hobo

"Like a hobo from a broken home
Nothing's gonna stop me”

We always joked that we were just like hobos! Not only did we actually sleep outside on the rooftop of a retail store with hobos on this trip, we were kinda hobo-ish ourselves.

Sleeping on rooftops. We showered in our swimsuits everyday on the beach showers. I remember sort of cleaning up at a truck stop once.

But hey. We all got to travel Florida on a tight budget!! We split gas 5 ways. It was amazing.

Aura Dione- Friends

I don’t like watching music videos usually, because a lot of times they tend to ruin the song for me. I think this is one of those times. This is another song that one of the Ukranian girls played in the car during our road trip.

I ended up liking the song, and I became such close friends with the 3 girls so fast that this song just really made me happy about the new friendship.

I even ended up going on a trip to visit them in New York a couple of years later! That trip will be featured on a different travel tunes tuesday.

Amy McDonald- This Is The Life

“Where you gonna sleep tonight?”

Another song whose lyrics fit PERFECTLY to be our theme song since we had no idea of the answer to that very question! Every night in the Florida Keys was a toss up.

Apart from the roof, another crazy place we ended up sleeping was in a street magician’s back yard!!!

Erin- Vapaa

You’d think this song would be Ukranian or Russian, but nope. I’m pretty sure it’s actually Finnish. Yet, I heard it straight from the iPhones of one of the Ukranian girls.

I thought it was really pretty and it definitely wasn’t a road trip song that I was expecting to hear! It got stuck in my head despite the fact that I have no idea what it’s saying.

С.К.А.Й. - Струна


The Ukrainians showed me a REAL Ukranian song, and not a Finnish song trying to trick me into thinking it’s Ukranian!

Another unexpected road trip song that makes me think of the amazing time I had with these new instal-friends (instant friends, not to be confused with instagram friends…because those aren’t real).

I bet you didn’t expect my FLORIDA playlist to consist of Ukranian and Finnish, but there ya have it!

What are some of your favorite travel tunes? Please share below, or in your own post with the #TravelTunesTuesday tag so we can find it!

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What a fun story. This makes me miss my youth of backpacking thru Europe. I still remember sleeping in the center square of Sienna during the Paleo because we went last minute.


omg that's AMAZING!!! I love that lol

aww Sometimes the best experience happen by chance!


aw for some reason it hid your comment!!! what the heck?! @karensuestudios did you get flagged on accident?

i think i am one of those who want to sleep outside from home but i slept on roof of my home


whoa you did? That's awesome! Sleeping outside is great if the weather is good!

Sounds like a great adventure you had. I like the Finnish and Ukranian songs.

Hi @nomadicsoul! You create wonderful memories! I love to travel and make new friends too!
I think this is a real life. :) One night you are surprised by the hospitality of the strangers and the other you sleep under the sky with your homeless friends. All the best! :)


Please tell this to my Dad! I'm not sure he sees it that way hahaha. But yes, I totally agree! As I was writing this, I was thinking I need to do more stuff like this!

Please dare me to do something crazy @see-it-feel-it!


This is the responsibility of fathers. ;) I think we have to meet one day and do something crazy together! 😅


Sounds like a good plan to me!!

Well very interesting road story... Looks like you had a great time... I wish I could also join you on a road trip some day... :) Thanks for sharing...


Thanks for reading! Yeah, I like traveling in unconventional ways!