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.

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.

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.

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.

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, 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.

About The Author

Valerie Conners

Valerie Conners is a travel writer, editor and digital producer who specializes in Florida travel, world's best beaches, outdoor travel, and romantic getaways. Her work has been featured by Conde Nast Traveler, BBC Travel, Travel Channel, and Frommer's travel guides. She hopes to snarf every frita and slurp up every $1 oyster happy hour in Miami.

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