Impossibly blue water makes for a striking backdrop to your lunch or dinner. (Photo: Valerie Conners)

Key West

Reaching Mile Zero: A Miami-Key West Road Trip

Take a stroll along Duval Street on your way to watch the nightly sunset spectacle at Mallory Square. (Photo: Alamy)

Sunset worship might be the closest thing to a religious experience that Key West offers, and anyone who experiences it will tell you, it’s a wonderful thing. If you’ve never been, Key West is a quirky, stranger-than-strange world. You might already know that Austin, TX’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 thankfully, it’s not about to change.

Stay Weird, Key West

Key West
Impossibly blue water makes for a striking backdrop to your lunch or dinner. (Photo: Valerie Conners)

It’s this pervasive oddness that visitors 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.

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 Durty Harry’s, fear not. There’s more to the island than the ubiquitous hordes slurping back booze on the Duval Crawl of bars would have you believe.

Test Your Book Smarts

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.

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

Key West
A selfie in front of the Southernmost Point is a tourist must-do in Key West. (Photo: Valerie Conners)

Sights, Suppers, and Sips

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 island’s 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.

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.

Finally, for a nightcap or pre-dinner drink, get thee to The Other Side, a hand-crafted cocktail bar. It’s located on the “other side” of The Porch, a popular craft beer bar. You’ll be smitten with the ambiance, and the drinks might just steal your heart.

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