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  • Writer's picturetylercates

In the Land of Hemingway and Parrotheads

On a personal level, the first couple of months of 2023 have been pretty rough. At the beginning of March, B and I decided that a getaway was not only needed, but extremely necessary. The only question was where to go.


Visiting Key West has been on my constantly evolving bucket list for quite some time. When I saw that one of my favorite singers, David Nail, was playing at the Key West Theatre on February 28 , it seemed to be a sign.


After spending a day in Washington, DC taking into the sights around the Tidal Basin and the Cherry Blossom, we flew directly to Key West. We stayed at the Southernmost Beach Resort, which was fabulous. Copious amounts of seaweed washing up made swimming at the beach less than ideal, but the resort had three pools, so swimming and soaking up some sun were covered.


Other than attending the David Nail concert, we had no plans which was the plan. Rest, relax, and go with the flow. We wanted to see all the usual tourist attractions, such as the Mile 0 marker, the Southernmost Point in the Continental United States, and the home of Ernest Hemingway, but lazing in and around the pool and barhopping were the top priorities.


Our favorite spot was Sloppy Joe's, also allegedly the favorite Key West saloon of Hemingway. I am sure it's changed since his day, but it was a very enjoyable time. I even had a Papa Doble in Hemingway's honor for my first drink here. Friendly, attentive staff, great drinks, live music, and a fun atmosphere made Sloppy Joe's a highlight of the trip.


We did not have a bad meal or experience at any establishment we went to in Key West., making it easy to see why it is such a popular vacation destination.

One of the quirks of Key West is the multitude of chickens that roam freely throughout the island. The roosters crow morning, noon, and night, making it extremely difficult to get any sleep. As you can tell from the photograph above, they go where they want go and do what they want to do. I can appreciate that vibe.

In my humble opinion, David Nail is a phenomenal singer and performer. It is absolutely criminal that mainstream country radio doesn't play his music more often, especially considering the garbage that they play far too much, but I digress.


If you're not familiar with Nail, I suggest checking him out. His biggest hits include, "Night's On Fire", "Red Light", "Kiss You Tonight", and "Whatever She's Got". Digging into his library a bit deeper, I like "Sunset Carousel", "Seattle", "Fighter", and "The Secret", which I think is the saddest song ever recorded. Unfortunately, he has so many great songs, it was impossible to fit them all into one set.

I would have loved to have visited Key West in Hemingway's day before it became so touristy, but I feel like that about almost everyplace and everything. It is still an amazing place.


A few days of warm weather, beautiful sunrises and sunsets, great music, food, and drinks is just what the doctor ordered to shake off this general malaise I have had for a few months and recharge my battery. I am already looking forward to our next adventure.


Thanks for reading and I'll talk to you soon!



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