My 1st Impression of Key West


My 1st Impression of Key West

“The bridge is ouuuuttt!!!”

This Arnold Schwarzenegger line from his 1994 film “True Lies” rang through my head (and car) a couple dozen times while making the trek down the historic overseas highway. Ever since seeing this cool 7-mile bridge in that movie I have wanted to make my way down through the Florida Keys. Unfortunately, my 1st impression of Key West did live up to this famous chase scene.


Key West is Busy

Sadly there were no daring helicopter rescues, explosions, or chase scenes. Instead, there was traffic. Lots of traffic. This amazingly scenic roadway that I had built up in my mind was replaced by bumper-to-bumper cars, RV’s, and road rage. Not the 1st impression of Key West I was hoping for but sadly a common scene. With no vacancy signs lit most of the time, Key West is a popular getaway– just not a getaway from crowds evidently.


Good luck grabbing that postcard picture from the southernmost point in the USA.

Key West is BIG

My 1st impression of Key West continued with the shock of just how big the island is. In my mind and with the smaller Keys we passed a long drive I envisioned a tiny town with character to spare. What I found on the drive into town was big box stores and fast food chains. To be fair this 1st impression of Key West was of New Town, which is about as charming as the name suggests. Also, the island was expanded by the US Navy years ago – evidently doubling (not really) the land area. Old Town is where the character of Key West can be found.

Key West is Touristy

With the traffic on the highway ride in I am not sure why this came as a surprise. My 1st impression of Key West’s Old Town was tackiness and tasteless junk. Store after store pushing t-shirts, cigars that aren’t even made in the Keys, and everything Key lime can be found along Duval Street. There you will also find cheesy bars, chain restaurants, and booths trying to sell you on crowded tours and attractions. Also a Walgreens in a very cool old theater! (see cover pic) It was a mix of what I dislike about Bourbon Street in New Orleans and the Vegas strip.


Beyond 1st Impressions of Key West

Thankfully this was just my 1st impression of Key West. I had a few days to experience it all and I’m happy to say that I was able to seek out some great places to eat and drink along the way. I’ll be sharing posts on those places soon but in the meantime here are some tips beyond my 1st impression of Key West:

Stay Here:


Eat here:

  • Caroline’s for peel and eat Florida pink shrimp and massive fish sandwiches.


  • Kermit’s key lime pie for key lime pie on a stick.
  • The Cuban Coffee Queen for fresh Cuban sandwiches and Cuban coffee (duh!)


Drink here:

  • The Green Parrot – the first (and last) bar on HWY1
  • Captain Tony’s Saloon – Hemingway’s original hangout
  • The Porch – historic house and separate beer and wine bar rooms

See here:

  • Hemingway house for an awesome tour and collection of six-toed cats!


  • Key West aquarium for its history and shark feedings.




  • Rent a bike! The best way to get around!


What say you?
What was your 1st impression of Key West?
Let’s hear it!

For more reviews from Key West and beyond see HERE.

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  • Jennifer Reynolds

    I actually really liked Duval Street. There are some hidden gems along there. Plus after relaxing during the day it’s nice to be able to walk along one strip for all of the night life you’d ever need….dive bars, nice lounges, restaurants, drag shows, food trucks, cigar shops, shopping, art…. the list goes on.

    • For sure! I warmed up to it but as a 1st impression it was not what I was expecting!

  • Quentin Reed

    I would love to check out Key West for the crazy festival they have around halloween. Looks absolutely insane but also super crowded!

  • Sonia Kluman

    I made trip from Miami to Key West and thought it was lovely. Was not to many people and enjoyed sunsets very much. Great pictures

    • Thanks Sonia! You must have visited midweek if it wasn’t busy! I was there in off season and there was still a lot of people coming in!

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  • Mirah Welday

    I agree, the Hemingway House was fun for me. I wasn’t a fan of the congestion in the center of Key West, the vibe was just not what I expected. But off the beaten path, Roostica (wood-fire pizzeria) on Stock Island had some amazing pizza! I would go all the way back there just for the Shrimp & Pesto Pizza!