I had planned on doing the whole cruise in one post, but then I started writing about Key West and let me tell you it was the highlight of our journey. This charming town offers so much to see and do and just a skip away from the port. While some opt for wheels, Jeremy and I decided to take it slow, strolling along and soaking in the island vibes.
Now, Key West isn’t just any old town – it’s full of history. We wandered down Duval Street, not just dodging tourists, but also chickens strutting their stuff like they own the place. And you know what? In a town as quirky as this, they kind of do.
But let’s talk literary legends. Hemingway himself spent his most prolific writing years right here in Key West during the 1930s. And he wasn’t the only one – Key West writers include Tennessee Williams, Shel Silverstein, Robert Frost, Elizabeth Bishop, and a whole lot more. It’s like the ultimate writers’ retreat, minus the stuffy conference rooms.
Back in the day, Key West made its fortunes from wrecking and salvaging ships that met their demise on the treacherous reefs and shallow waters offshore. Locals raked in the dough by auctioning off or reselling the valuable cargo salvaged from these shipwrecks.
Hard Rock Café
This was the only official HRC on our journey. This café, sprouting up in ’96, is as unique as a pineapple in a fruit salad. Tucked away on Duval Street, it’s like the chameleon of cafes, blending seamlessly into the surroundings without screaming “look at me, I’m a massive eyesore!”
This three-story Victorian beauty is rumored to be haunted by its original owner, Robert Curry. They say old Bob still roams the halls, but during our visit, he must’ve been taking a ghostly siesta or something because we didn’t catch a glimpse.
But enough about the spooky stuff, let’s talk shop… gift shop, that is. The gift shop is outside. I only ventured inside for a bathroom break, but hey, gotta give credit where it’s due: the food at HRC is always on point. However, we were on a mission to taste the local flavors.
I’ve got the OG shot glass with the logo and the so-called “city glass,” a little souvenir with local flair. But wait, there’s more! With a dash of that legendary HRC customer service, I casually mentioned to the cashier that I needed a different glass to complete my collection. Next thing you know, she disappears into the depths of the café, only to return with a rare gem—a glass commemorating the Key West HRC as a stop on a pub crawl. Now that’s what I call service with a side of awesome!
Hemingway House
I decided to write this article with all my research and then asked ChatGPT to rewrite it in the style of Hemingway. Check it out:
We made the grievous error of procrastination when it came to paying homage to the Hemingway House. They whisper it’s the pinnacle of tourist allure in Key West, yet we, in our folly, arrived belatedly only to confront a queue stretching longer than Hemingway’s literary opus. With the relentless tick-tock of the clock and the looming departure of our vessel, we were compelled to forgo the opportunity to traverse the hallowed halls of this iconic abode.
But fret not, esteemed reader, for I salvaged remnants of our near odyssey. A snapshot here, a fleeting glimpse there capturing the visage of the renowned house and seizing moments with its storied feline denizens.
Did you know that Hemingway, in a gesture of maritime benevolence, was bestowed a six-toed feline by a magnanimous ship’s captain? Legend holds that a lineage of nearly sixty cats currently prowling the museum’s precincts trace their lineage back to this progenitor, christened Snow White.
The Hemingway House, an architectural relic dating back to 1851, bore witness to an epoch of passion and literary luminosity as Hemingway and his consort, Pauline, held sway within its walls from 1931 to 1939. Yet, as with all sagas, theirs unfolded with twists and turns aplenty. The duo parted ways in 1940, though Pauline’s tenure endured until her demise in 1951. As for Hemingway himself, his narrative met a tragic denouement with his premature departure from this mortal coil in 1961.
I know I would have never been able to write like that. Cool. My style is more to the point with a touch of humor here and there.
Margaritaville
It’s a bittersweet reminder that Jimmy Buffet’s music will continue to serenade us, even after his recent passing in early September. His laid-back vibe, immortalized in his albums, casinos, resorts, and restaurants, ensures that his legacy will endure.
Speaking of his restaurants, we’ve been to one before and enjoyed the food. But, as I mentioned earlier, our mission was to savor the local flavors. Still, we popped in to soak up the atmosphere and have a chat with the friendly folks manning the gift shop. Glad we did because they had shot glasses with the city’s name — You know, I’m a sucker for those souvenirs.
Southernmost Tip of the US
I was here once before, when I was younger, on a family adventure to Disneyworld. That’s right, we went to Orlando but also made the drive to Miami and Key West. The Crockett clan was all about squeezing every ounce of fun out of our trips. When it came to traveling, we were like a well-oiled machine, determined to see and do it all.
Originally just a wooden sign back in the 1970’s, this monument evolved into the Southernmost Point Buoy—a legit tourist attraction dedicated by the city on September 10, 1983. Standing tall at 12 feet and stretching 7 feet wide, this buoy continues to greet visitors.
Now, fast forward to the present day, and here we are, standing at the iconic Southernmost Point in Key West. But this time, the place is packed.
There’s a line stretching longer than a Disney World queue, all waiting to snap a pic with that famous red and yellow landmark.
Not one to be deterred, I hatched a cunning plan: play dumb and sneak in from the right instead of the left. And would you believe it? It worked. I got my obligatory tourist pics, and made a smooth getaway.
Father Kee Statue
Near the marker stands a bronze statue, a tribute to Bishop Albert Kee, a revered preacher and businessman.
Erected in March 2015, the statue commemorates Bishop Kee’s legacy as Key West’s official goodwill ambassador.
Every day, Bishop Kee would greet visitors and show off the tradition of conch blowing. No one seemed to be paying much attention to Kee, most of the tourists wanted their southernmost selfie and were gone.
Truman Little White House
While we didn’t have time for a tour, I snapped a few pics of the house and the area. If we were loaded, I could totally see us chilling in one of those mansions.
Back in 1890, they built what’s now called the Little White House, originally as Quarters for some Navy bigwigs.
It went through some changes over the years – from hosting President Taft on his Panama Canal check-in to giving Thomas Edison a home while he cooked up wartime gadgets.
Even during World War II, this spot was a key player, safeguarding ships from U-boats. It was also Truman’s go-to vacation spot during his presidency.
Capt. Tony’s Saloon
Captain Tony’s Saloon holds a special place in the heart of Jimmy Buffett fans. It’s where Buffett got his start in the early 1970s, often singing in exchange for tequila. He even immortalized the bar and its owner, Captain Tony, in his iconic song “Last Mango in Paris.”
The building has a lot of history too. Built in 1852, it began as an icehouse and morgue before turning into a telegraph station during the Spanish American War. Over the years, it was a cigar factory, a bordello, and several speakeasies. In the 1930s, it became Sloppy Joe’s Bar, frequented by Ernest Hemingway himself. And finally, in 1968, it took on the name Captain Tony’s Saloon under the ownership of Tony Tarracino.
Mangoes
As we strolled along Duval Street, we were scouting the perfect spot to grab a bite, a colorful pride flag caught our eye, and we thought, “Perfect”
Enter Mangoes—a charming joint that’s been serving the community since 1980. Jeremy, always the adventurous eater, opted for the beef tacos, but with a twist—he asked for them to be served more like nachos.
They were massive—enough to feed a small army (or at least, that’s what we told ourselves). As for me, I went for the Island Dog—a Wagyu Beef Dog topped with pineapple relish and creole mustard.
Oh, hell yeah! With our bellies full, we rested on the patio, soaking up the sunshine and enjoying some prime tourists-watching.
Irish Kevin’s Bar
Sometimes, the best discoveries are the unplanned ones, like stumbling upon a place with a name as promising as Kevin’s. And let me tell you, it did not disappoint!
Packed to the brim with folks chowing down and raising a toast, this joint has been serving tourists since 1998. If we ever find ourselves back in Key West, you can bet we’ll be spending some quality time here.
After a quick look around, we made a beeline for the gift shop, where I scored a shot glass from Irish Kevin’s Bar!
Sloppy Joe’s Bar
At the corner of Greene and Duval Street stands Sloppy Joe’s Bar, a Key West icon since 1937, run by the same family since 1978. This joint’s main bar opened in 1917 and Joe’s Tap Room dates to 1892.
The place has been on the National Register of Historic Places since 2006. When Jeremy and I swung by, we weren’t there for the history lesson, just popped into the gift shop. Shot glasses? You betcha.
Gay District
Somewhere in between all the touristy spots and the southernmost tip lies a bustling gay district. Key West has that liberal vibe with plenty of shops and eateries.
But hey, straight folks, don’t fret – this district’s open to all. We hit up a bar where there was a whole family munching away, they probably didn’t even know it was a gay joint.
We hopped around a few spots, snagged some rainbow gear at Graffiti, a pride-themed gift shop. Scored myself a Santa rainbow hat and Jeremy got a snazzy rainbow beanie.
The owner pointed us to Bourbon Street Pub across the street. Nice place, killer drinks, and even though we stuck out like tourists, folks were all very friendly.
To see more of our Christmas Cruise trip or other trips, check out Road Trips
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