I thought about how to write this entry for a while (whether I should break it up by individual sites or not) but after revisiting Key West for the fourth time in my life I realized that Key West trips should be considered one experience. Laying just 90 miles north of Cuba, you will find one of the most radical places in America. After all, the city did secede from the United States and had one of the first openly gay mayors.
One of the most important assets of a Key West adventure is getting there. In my previous visits, I have always driven via US 1. The drive is one of the most scenic drives you could possibly imagine. But this I took the Key West Express. The Key West Express is a cruise line that departs from either Ft. Myers or Marco Island. There is a docked Key West Express ship in Tampa but unfortunately there is no service from Tampa. It really is a shame because I would probably visit more frequently if it did.
Saturday morning we woke up at 4AM and headed south to Ft. Myers Beach. It is imperative that all you GPS users out there note that the Key West Express launches from the city of Ft. Myers Beach, not Ft. Myers. If you make this mistake you might find yourself wondering where in the hell all of the boats are.

When we arrived at the dock, I skipped on the Dramamine. Part of me was hoping for some sea sickness adventure but the Key West Express is such a huge ship it wasn’t necessary anyways. When we got out of the car and headed towards the boat it struck me as really strange at how many employees this cruise line had. Business must be booming in these tough times if the parking lot needed 10 crew members. Then we went to pick up the tickets and found out we had to pay $16 for parking and it slowly started to make sense.

We got on aboard and realized how nice this cruise line really was. Seating and tables everywhere, multiple TV’s broadcasting the news and movies, and even a few bars. People weren’t hesitating to buy drinks at 9 AM either. The boat ride quickly became a pre-noon drinking binge party for most passengers. When we launched out captain came on the speaker to welcome us and his New York Italian accent was overbearing and almost made me question his ability to captain such a big ship. To overcome this doubt I decided I needed a mimosa and some fresh air. So I hit up the back deck and watched the coastline for a while. The silhouettes of the hotels on the coast were amazing to watch. They remind you of all the tourism and destruction humans have done to the Florida coastline.

I looked at the clock and it was only 9:30 so I decided to take a nap. I awoke as my phone started vibrating with several emails and text messages as I found myself in a pool of Florida stickiness. I must of have fallen asleep in the worst place because the upper deck laid in the perfect position between me and the sun. I woke up with a tan line split right down my face like I was straight out of a Batman comic book.
The islands of mangroves started to appear and I knew we were close. The people clustered to the door as the shipmates started hooking the boat to dock and the excitement in the air could be felt. The cruise line offered a guided trolley tour around Key West (something I have never done) so we thought it would be a good idea to check it out. When we got off the boat we waited for the rest of the ship to clear and gather for the tour and we got in the back seat of a trolly.

Flagler Museum

I tried to snag a few photos of some unique sites while riding but I found it quite difficult since out seats were facing outward from the rear of the train.

As we were riding in the back of the train, one of the local “Conchs” skateboarded up to us and grabbed on. It was entertaining to watch and great to feel the free spirited atmosphere of Key West.

And of course, after the guided tour, we did what all Key West tourists do. We headed to Duval Street. If you’ve never been to Duval Street prepare yourself for an all day everyday party. Actually, you can’t do that. There is no preparation for the things you will encounter on Duval Street. It just exists.

All of the bars are outdoors since the climate is perfect year round and you can just bar hop all day. Rum Runners are probably the most easily obtainable drink on the island and are the perfect drink to keep your body cool through the warm weather.
Sitting there, enjoying myself, I looked up and saw a bucket with an Ear-X-Tacy sticker. It was nice to know that Kentucky had made its presence known so far away from home. And then I remembered… It was Kentucky Derby Day. There is only one place on earth I would ever consider being besides Louisville on Kentucky Derby Day and that’s Key West… but if I had one wish in life, I’d wish that I could be in Louisville on every Kentucky Derby Day. So I made due.
At this precise moment, believe it or not, the trumpet was playing and the horses were lined up in the gate on the TV in front of me. Some guys beside me had a Derby Day styled hat on and a Churchill in their mouths. It was comforting to know the Derby was watched everywhere. Key West loved the idea that name of the horse that won the Kentucky Derby was named “I’ll Have Another.” Partying ensued.
We left the bar and walked out into the gathering of people in the street. Did I mention that it just happened the weekend we decided to visit Key West was also the Singer Songwriter’s Festival. There was a stage set up with performances going on all day. There was this straight western film styled Mexican music band playing when we approached. I swear I thought Clint Eastwood was going to appear from a cloud of smoke at any given moment.
Key West goes bananas at night. You will eventually find yourself in a crowded sea of people being swept from one bar to the next. That is, until you eventually make it all the way to the end of the island. At this point, you realize your not in your type of bars any more. But, when in Key West, do as the Conchs do and snag a great photo opportunity…

There’s no reason to feel concerned on Duval Street late at night because everyone there is just trying to have a good time and you will eventually find a cab ride back to your hotel on the other side of the island. You might even be so lucky as to acquire another passenger on the way and split the fare like I was. Then you crash for a few hours, re-energize and do it all again the next day!
We headed back to Duval Street to see the sights that we missed on our first day of adventure. We knew the Hemingway house was a must, maybe even check out the light house. I led the way towards the Hemingway house and I just happened to stumble upon a sight I hadn’t been to before. Mile marker 0. We had passed it on the trolley but I couldnt snag a good shot. So I was glad to be back. The tour guide let us know that this sign is frequently stolen. I could see that as it was quadruple bolted to the pole.

Eventually, we made it to the Hemingway house(a sight I had been to before, but wanted to make sure my roommate had the opportunity to visit). It is one of the most amazing properties in America and man I wish I owned it. I can only imagine how great it would feel to wake up with surrounding sunlight beaming into my bedroom, walk out onto a 2nd-story wraparound porch, and then head to my pool house to tacking my writing excursions for the day.

Viewing the KW Lighthouse from the Hemingway porch

Where the magic happened
My roommate and I roamed the grounds of the Hemingway property and found some benches great for thinking. You just feel like you want to be the next Great American Author when your here. It seems like the setting would be perfect for it.


We headed out and started our way back towards the boat to take us home. But before we did I stumbled into the Key West Key Lime Pie Company where I picked up a few items. A key lime slushie, a jar of key lime jelly and a key lime cook book. A must visit store if I must say so.