Florida Keys Weekend Road Trip Part 2: Key West

Key West Florida

Sunset worship might be the closest thing to a religious experience that Key West offers, and I gotta say, it’s a helluva thing. If you’ve never been, Key West is a quirky, stranger-than-strange world. You know how Austin’s motto is “Keep Austin Weird”? Well, Key West doesn’t have to make such commands. Key West, if you dig past its bros-on-a-bar-crawl exterior, is nothing but weird. And it’s not about to change.

key west
A post-sunset celebration at Mallory Square. (Joe Parks via Flickr)

It’s this pervasive oddness that I love, an island’s unexpected corners tucked into the cracks of falling-down front porches, or behind a jungle of orchid-covered trees. It’s almost as if someone took America, turned it upside down, and gave it a good shake. All the folks who couldn’t quite walk the straight line, who were looking for something more — or less — or different from the straightforward all filtered down to the Southernmost Point in the United States.

Key West

If you do make it down here, and find yourself turned off (or worse, turned on) by the sloppy crew at Sloppy Joe’s, or the wet t-shirt contests at Dirty Harry’s, fear not. There’s more to the island than the ubiquitous hordes slurping back booze on the Duval Crawl would have you believe.

First, get your literature fix. Get thee to The Ernest Hemingway Home and Museum, and see the spot America’s king of brevity called home. Traipse up the stairs of the guest house to see the desk where he spent his days writing, before hitting a bar or fishing boat. Or more likely, both.

Hemingway Home
Papa’s desk and writing room.

Take a moment to respect another brilliant writer, Tennessee Williams, who also lived on Key West, at the Tennessee Williams Key West Exhibit.

From here, you might want to make like a tourist (because, let’s face it, we’re ALL tourists), and snap a picture at the Southernmost Point.

Wander through the islands streets, side streets, and alleys and admire the little (and large) homes and porches; many of them are dreamy places in style and decor. I fell in love with the old-fashioned lamps softly lighting so many porches.

Hemingway Home
Hemingway had a good porch.

There’s no shortage of spots to eat dinner, but too many offer generic dining experiences. Stop into Blue Heaven for brunch; this iconic spot where chickens roam free and entrees ooze delicious calorie-filled awesomeness is worth the inevitable wait.

For dinner, we enjoyed eating on the porch of Santiago’s Bodega. The wine list was impressive, the small plates delicious, and our waiter knowledgeable and friendly.

the other side
The Other Side. (The Other Side via Facebook)

Finally, for a nightcap or pre-dinner drink, I became a little obsessed with The Other Side, a hand-crafted cocktail bar (and yes, I hate that term – how the hell else do you make a drink if not with your hands, but you guys know what I mean…). It’s located on the “other side” of The Porch, a popular craft beer bar. The service was truly sucky, but the ambiance and the drinks stole my heart.




  1. We just missed each other! Our Key West and yours were very different (with a few exceptions). I’m not surprised. It’s a diverse place.

    We walked the moat walls of Dry Tortuga; were unexpectedly moved by slave ship relics displayed at the Mel Fisher marine heritage museum; watched iguanas bask and went swimming at Fort Zachary Taylor; ate multiple meals at The Cafe (a vegetarian restaurant I’d eat at by choice if it were transplanted to Philly); and wowed the regular folks with our salsa moves at El Meson de Pepe, accompanied by bad salsa covers of American pop songs sung in English by a two-man band.

    And yes, we did take in the Hemingway House. In front of which a young poet with a typewriter wrote me a lovely poem on the subject of my father’s naval service at Key West, so many years ago.

    Good times!

    But I was most impressed when I learned that the giant cruise ships are contractually obligated to MOVE THEIR ASSES OUT OF THE WAY at sunset.

    • Valerie Conners says:

      Tom – that sounds wonderful! I’ve yet to go to Dry Tortuga, and really want to make it a priority next year. I’ve been to the fort and Mel Fisher museum in the past but that was YEARS ago; I’d say I’m long overdue for a return to both. We squeezed in what we could in 18 hours or so; id like to indulge in a longer stint next time. So glad you enjoyed your trip; it really sounds splendid!