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Travel: Key West – What To Do


It’s Key West week!  And what a week it was.  It was sunny and it was beautiful and it was incredibly relaxed.  The island exudes calm.  Relaxation seeps into the soles of your feet as you walk the streets.  Dramatic?  Maybe.  No one hurries on Key West.  No one wears long pants!  Key West is open-toed, bare-knee meandering at its finest.

Our week was a mix of perfect nothing and incredible adventure.  We spent our days lazing away by the pool, walking up and down and up and down the streets exploring the history of the island, and trying our hand at more than one watercraft.  We rented bikes, but K and I rarely rode them–I’m mediocre on foot, but on wheels surrounded by traffic, I’m downright dangerous.

It’s been a while since I’ve felt so calm, so relaxed, and had so much fun.  Sure, I feel best around water, by which I was surrounded.  But more than that, it was so great because I was also surrounded by great food, beautiful things, and really, really great company.

Here’s what we did (and what I can gently suggest you do too, should you ever travel to the southernmost). 

Sunset at Fort Zach Beach

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Key West is renowned for it’s sunsets, or more specifically, it’s sunset celebrations.  The town gathers at Mallory Square to cheer the sunset, a task I fully support bringing into your every day life.  However, I’d humbly suggest taking in the sunset on Fort Zachary Taylor Beach at Fort Zachary Taylor State Park.  There are jetties that go out into the water where people stand and watch the sunset unimpeded, save for an errant sailboat or, you know, cruise ship.  We saw both.

Just when you think it couldn’t be more beautiful, the sun dips deeper and the color grows more saturated and it is.  It’s more beautiful, until the next moment at least.

The state park closes at sunset, so if you arrive about an hour before, you can get in and then walk out once the show’s over.  It’s well worth it.

Southernmost Point (90 Miles to Cuba!)

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Real talk.  This was a site I needed to check off a list.  A list that someone made in some guidebook that said “Don’t leave Key West without doing this thing right here!”

Southernmost Point is indeed the southernmost point of the United States, and it is indeed 90 miles from Cuba.  It is also, indeed, absolutely overrun with tourists (just like you!) who want to have their picture made at the southernmost point.  I suggest going, seeing, and walking away.

It made me think about how I travel and why I travel.  Am I traveling for a well placed Instagram, or at the very least a picture that will stay on my phone until I run out of space?  Or am I traveling because I want to inhabit a place, if only for a little while?  I think way too often it’s the former, but it should be the latter.  Go here, see it, be in that place, and then walk away.  Don’t wait in that line–you saw it.  With your eyes!

Bonus: right around the corner from Southermost point are some truly great views of the ocean with some really cool hotels.  There are lots of great things to explore down that way.

Fort Zachary Taylor State Park

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Yes, watch the sunset.  But also stay for the Fort!  Fort Zachary Taylor State Park is an historic civil war fort and great beach all in one.  It was essentially undiscovered, which I think is weird because clearly it was there, discovered, but what that really means is that it was owned by the US Navy in an era when the US Navy didn’t have a lot of money to explore abandoned forts.  And so it remained, uninhabited and unexplored.  When archaeologists went into the Fort in the 1960’s, they found the largest cache of civil war relics ever found.

It’s worth a trip for the views of the ocean, the civil war era canons (if you’re into that sort of military history thing–I am) and the beautiful brick walls.



Fury Jet Ski Tours offer a 2 hour tour around the perimeter of Key West.  It’s intense and not at all calm nor relaxing, instead, it’s exhilarating.  I was in the slow group, which as my sister in law pointed out should not be called the slow group, as my average speed was about 30 mph.  The fast group, however, topped out at 45 mph, which I think is insane.  There are waves out there.  It’s the ocean!

It’s a lot of fun, though.  You’ll be sore, so prepare, but when else will you get to jet ski around an island?  I think it was worth it (but I didn’t fall off of my jet ski…)

Key West Cemetery 


This may sound a little strange, but exploring the Key West Cemetery was one of my favorite mornings.  K and I set out for a walk, and walked over to this cemetery–the only one on the island–and wandered through.  It’s full of history, both recent and not so recent.  I think I liked it most because I got to spend it the morning with K, meandering through, respectfully looking, wondering, and wandering.  If you like history, and are looking for something off the beaten path, go here.  There is a map you can pick up at the entrance which offers points of interest, but I’d suggest just walking.

I learned the most about Key West here, as it’s a real a cross section of everyone who has lived on the island for over 100 years.

Ernest Hemingway’s House

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Come for the literary history, stay for the cats.  That should be the motto of the Ernest Hemingway House.  This was my favorite thing we did on this trip.  I love Hemingway, I think his breadth of work and his personal history is fascinating, but I also love cats, and 6-toed cats especially.  I had a 6-toed cat named Tigger, and he was a gem.

The residence is exquisite.  It’s at the same time ornate and understated.  It’s tucked behind luscious trees and gardens and is an architectural masterpiece.  Hemingway was married to his second wife while he lived here, and both were into Spanish art and furniture.  The king sized headboard, an almost unheard of concept at the time, was custom made and was sourced from a gate to a Spanish monastery that the Hemingways were taken with.  It’s something to see on it’s own.

And then there’s the cats.  It’s like Easter egg hunting.  They’re tucked in flower pots, under ferns, back behind bushes, and smack in the middle of sidewalks.  And they don’t give a fig that you’re there.  I don’t mean that they like that you’re there, I mean that they don’t care that you’re there.  Pet them or don’t–they couldn’t care less.  Living with a cat like Tyson, who is as needy as they come, this threw me.  Also, that cat?  On the shirts?  That’s the gift shop, and those shirts are actively for sale.  I love this place.

Chartered Fishing Boat

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I wanted to see the cats (and yeah, Hemingway stuff too…) but my brother wanted to fish.  Me, having never been fishing, was all for it.  So, one of our mornings we woke before the sun and after too few hours of sleep to ride our bikes over to the chartered boat dock.  We met Captain Rick and First Mate Ben, and off we went on a Chartered Fishing Boat that my brother found.  We were in search of Mahi Mahi and King Fish and Baracuda and Bonita.  I reeled in a King Fish, which I can’t back up with a picture because apparently they’re quite mean and it was dangerous.  I really did, though!

My sister in law got a baracuda, which was adequately dangerous looking.  After our four-hour tour (a time frame that was absolutely enough–no need for a 6- or 8-hour trip in my non-fishing opinion), we stepped off the boat, 5 fishes richer, one sea-sick passenger poorer, and just in time for lunch.  We spent the rest of the day relaxing by the pool.  Vacation should only start before 6am if you get to take a nap in the afternoon.

When we weren’t doing those things, we were walking.  We were eating.  We were laying by the pool.  There is something for everyone in Key West, and I can’t recommend it enough.

Stay tuned this week for more about my trip to Key West.  Coming up: What to Eat, a whole lot of pictures, what I packed, and a Key West-Inspired cocktail!

2 thoughts on “Travel: Key West – What To Do

  1. Pingback: Wear: My Key West Suitcase | See Hatsie

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