Miami & Key West – Trip Report – Part II

Congrats on making it to the Key West portion!


Note: For brevity, details about the Casa Marina have been written as a separate hotel review post here.  


As I left Homestead behind, civilization abruptly faded from the rearview mirror, and eventually I came to the beginning of the Overseas Highway that connects the Keys with the Florida mainland.  Fortunately, traffic was light on this Saturday, particularly after I passed a popular boat show on Key Largo.


Overseas Highway Florida Keys

My excitement only grew as the picture-perfect islands and seas unfolded before me.  I wanted to jump in and never get out. [Presumably, the mer-folk would adopt me? I didn’t think that through much.] The anticipation and average speed of 45 mph meant that the mileage didn’t quite tick down as fast as I would have liked, but I eventually settled on just enjoying the view.  The Keys were in surprisingly good condition post-Irma, and the most poignant reminder of nature’s destructive power wasn’t recent damage.  Rather, it was the remnants of Henry Flagler’s railroad.


When I eventually crossed onto Key West, I easily navigated to the Casa Marina – originally built as a resort for Flagler’s railroad passengers. As it’s on the southern coast, I just turned left onto A1A and followed that for a couple of miles.  I pulled around by the porte cochere and checked in. I was instructed to not go to the room quite yet.  No problem! I wanted to check out the beach.


After washing up from the beach, I put on my boots and began the 45 minute walk to Shrimp Daddy’s to meet B.  I wanted to see a bit of Key West, I didn’t fancy figuring out parking, and I am too cheap to pay for a taxi when I have a perfectly suitable car AND pair of legs. Lucky me, as I saw a Thai-Japanese restaurant where I could get some sushi en route.


Even with the dinner stop, I arrived in time.  Shrimp Daddy’s is a local dive bar, complete with all-you-can-breathe secondhand smoke and a dim lighting that hides all flaws. B’s stories were fascinating. While he did data analytics now (is the universe trying to tell me something?), his past included a stint in Hawaii and English teaching in Korea. My liver quailed in fear as he described the apparently ritualized sadism of drinking with one’s boss. “This will be a self-study day everyone,” because Teacher is hung-over to the point of death was (still is?) apparently a thing.


B’s transition to being a digital nomad was interesting to me. His company decided that his team was non-essential and could work from anywhere. He chose Key West.  He was looking to move on soon though, as Key West could be difficult socially.  I understood, as Hawaii was like that. The transient nature of the transplants (aggravated by very high living costs) and the constant flow of here-today-gone-tomorrow tourists can grind one down.


After two of the cheapest beers in Key West ($3.25 each) and by now smelling like an ash tray, it was time to call it a day. I caught an uber back to the Casa Marina to make a – personal appointment (oh, Grindr!).  But, you won’t hear a word more about that.


The next morning, I used my $15 Honors diamond voucher at the Casa Marina’s breakfast buffet.  I was happy. I indulged in a few extra carbs given that I’d be in the water snorkeling today!


I had booked myself on a Blu Q all-male, clothing-optional snorkeling/kayaking catamaran trip!  I’ve never been snorkeling, so I looked forward to swimming with the sashimi…I mean fish.


I put together a bag including a towel, various sunscreens (because I’m a ginger), and hunted for something bandana-ish. I guessed that a hat would blow away.  Eventually, I found what is used by the Key West boat crews for sun protection. It’s a synthetic fabric “tube” – a Buff – that can be manipulated into various uses.  $10 – why not? I came to like it. In classic James McCormack form, I bought it 4 minutes before boarding time @ 10:45 AM.


At the boat, I chatted a bit before boarding with my fellow guests before we all kicked off our shoes for boarding. Yay!  The first mate Thomas offered us water or soda. Ice water in hand, a brief safety demonstration was given, and we were underway.

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Tom was a great first mate!

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It wasn’t long before patrons stripped down to swimwear or nothing at all.  As is usual in such gay environments, age and quantity of clothing worn are inversely correlated. I bucked the trend for being the youngest on board and in my commando print Budgy Smugglers. The early 30s couple had boardshorts – booo!  The oldsters gave us a lesson in body confidence with nary a stitch on. (My gingerness doesn’t let me expose ‘those’ areas)


When we were within a few minutes of the snorkeling spot, I put on yet more sunscreen and got my snorkeling mask ready. A nearby boat advised us that the spot they just left had fish, was clear, and had no current. Yay for us.


The strangest navy ship I have ever seen

After a few seconds getting used to the flippers, I found them wonderful. My diving speed versus non-augmented feet was impressive. The sights down below were marvelous – bright (but not optimally health – far from it) coral and many-colored fish were in abundance.


When Thomas, our leader into the open water, led us back to the boat, we found that the captain had carved up a pineapple, put out some grapes, and was serving adult beverages. I opted for a white wine and water.  I noted the exceptional flavor of the pineapple, to find out that it was fresh from his front yard!  That’ll do it.


After some chatting and noshing, the Captain furnished lunch.  Pulled pork, rolls or gluten free tortillas, cole slaw, and pasta salad were on offer. I opted for pork and cole slaw. Delicious!


Due to the not-much-fun that is costochondritis, I opted out of kayaking in favor of another dip swimming in the 81 degree (Fahrenheit) water.


By now, our time was coming to an end.  The Captain passed around cookies (I declined), and we were soon heading back to Key West.


After a brief stroll around the neighborhood by the docks, I made my way to the Island House. Non-hotel guests can visit the bar and enjoy the facilities for $30. I decided to give it a go. The locker room, sauna, and steam room were decidedly bath house-like in vibe.  I decided to let the steam room patrons in particular have some privacy and decamped to the pool to relax. Overall, it wasn’t bad, but I think my $30 could be spent elsewhere.  Then again, I am not part of “generation bathhouse.”


After a run and yet another sushi dinner, it was time to call it a day, make a decaf espresso, vomit at the news, and go to bed.  As I drifted to sleep, I contemplated if all of this sushi had made me of interest for commercial mercury extraction. What’s your side hustle, fellow serf?


The adult-only pool at the Casa Marina

I arranged for a late check-out on Monday 3/18. Mostly, I spent it on a long breakfast and lounging by the pool in my yukata, a Japanese summer robe.


At last, I had some time to wander around and explore Key West a bit. I donned my boots, wandered around, and mailed some post cards to friends in Honolulu and New Zealand, before meeting B again for another drink.

Digital Nomad Bar humor
You can’t beat the juxtaposition



For my final night, I checked into the Seashell Motel.  As this night was paid with cash, I found the cheapest private room I could – $174 + taxes.  It was clean and basic, though the aircon was arctic strength. Score!


The next morning was my last in Key West. I decided to enjoy it at Fort Zachary Taylor, a historic fort and home to what I think is the best beach in Key West.  There’s some pebbled bits, but the water is more suited to swimming and frolicking in the low waves.  Yay!

After changing, it was time to head north with a stop to see my grandparents. More to come.


 – James out!


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