Road Walk to Key West: Chapter 8

Sunday, December 22nd, 2019

We didn’t get to sleep long outside of the church since it began to drizzle around 2 in the morning. The wind was blowing our bivies, sleep pads, and sleeping bags all over as we quickly packed up our gear, and searched for an awning to hide under. Of course, the moment we finished packing, the rain stopped.

We only got two hours of sleep, and that would be all we would get. We sat on the picnic benches outside of the “Tower of Pizza” and decided to stay there until businesses opened up. Not only did we have a roof over our heads, but there was free WiFi! Sleep deprivation sucks, but it could be worse. Way, way worse.

We weren’t there long until we received a visit from Key Largo’s finest. A police car rolled up, and one of the cops got out and started questioning us. We shared our story. How far we’ve come, where we were heading, and how we were just looking for a safe place to rest until we could grab coffee somewhere. We told him we debated sleeping in the brush, but there was a decent sized homeless population around, and we weren’t trying to be vulnerable. He was shocked, and waved over the female cop who was waiting in the car.

“Can you believe this? They walked all the way here from Alabama, and are heading to Key West.”

We showed them some of our pictures, and I think they realized we weren’t going to be causing any trouble. They came out because they received a call about “two suspicious people” hanging out front of a closed business, and they just wanted to make sure we weren’t trying to break in. He asked if he could see one of our IDs so he could run it through the system; in the name of protocol. Two more cop cars showed up but were waved away from the male cop. All went well. We gave several handshakes, they wished us a safe journey, and we went back to using the free WiFi as we waited for the Starbucks down the street to open their doors.

We drank some coffee at Starbuck, then searched for a place to eat. I had read good things about a place called “DJ’s Diner”. Unfortunately it was out of business, but a new one called “High Tide” took its place. We ordered coffee, and looked at the menu. The prices were super steep, even for a tourist destination! We would’ve went somewhere else after looking at the menu if we hadn’t ordered coffee already. The portions were small, but at least the food was good.

We hiked along bike trails once we left, and it was still early, so most places were still closed. We walked by “Mrs. Macs Kitchen” which was sadly closed as well. We had eaten there last time we passed through, and I was itching for some Key Lime pie. We would eventually get some at “Harriette’s Restaurant”. We were both a bit bummed that we didn’t hold out on breakfast a bit longer. This place was awesome!


Our next stop was “Sunrise Cuban Cafe” for some authentic Cuban coffee. That hit the spot! We were wired as we zoomed into Islamorada.


We passed through Plantation Key and checked out the “Old Tavernier Gift Shop”. There was a lovable kitty named Sasha there who got lots of pets from us before were visited the “Rain Barrel Village”. This place had a giant lobster out front, and a labyrinth of tiny shops inside.


We crossed Snake Creek into Windley Key. We stopped at the “Ocean View Sports Pub” to eat a late lunch of burgers and nachos. It was a Pittsburgh Steelers bar and there were several football games on. It was getting rowdy! After a while, we were getting that bad vibe, that we weren’t welcome there anymore. When you smell bad and look homeless, that tends to happen. We paid for our meal and debated where we would be sleeping.


There were thunderstorms in the forecast, and there were limited businesses up ahead that potentially had awnings to take cover under. We stopped at Publix to grab our resupply for the next day, and bit the bullet. We booked at room at “Pines and Palms Resort,” which was one of the cheapest options available, but wound up being really, really nice!


The lady at the front desk was really welcoming and interested to hear about our journey. We had walked only about 21 miles for the day, but wouldn’t regret our decision. As we settled in our room, we listened to the thunderstorm pass through overnight. We were just happy to be dry.

Jump Ahead to Road Walk to Key West: Chapter 9

Jump Back to Road Trip to Key West: Chapter 7


Start from The Beginning

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s