I was never a beach girl; I grew up on the coast dreaming of dense forests and old mountains. My greatest dream is to build a triangle cabin somewhere in Appalachia and hibernate all year with a giant dog, a wood burning stove, and plenty of marshmallows.
But halfway through my only year as a career girl, I decided I needed to see a tropical beach, sit somewhere in a bathing suit with the waves lapping at me, watching brightly colored fish swim by.
14 hours later, I found myself unpacking my bag in a room off the veranda of Duval House.
Key West is one of those places that just feels great—here, anything goes. Chickens running across the square, pina coladas any time of the day, and plenty of flip-flopped, sunburnt, bathing suit-wrapped people no matter if it's the beach or a nice restaurant. Island time, is what they call it. Perfect, is what I call it.
Where To Stay
Duval House. If you need an introduction to Duval Street then here it is: it's ultimately the center of everything. Bookended by hot tourist locations on either side, Duval House is located in the more residential section (with plenty of Vespas to rent and bites to eat) of Duval Street far enough away from the noise not to hear it but close enough to get it in event of some much needed party time. With air conditioned rooms opening onto wooden porches and a sumptuous backyard garden with breakfast and pools, I'd never come to the Keys and stay anywhere else.
Where To Eat
Le Petite Paris. For a late breakfast or a lunch out from the sun, stop by La Petite Paris for a grilled chicken and tomato panini, an avocado burger, or even just an ice cold Coke. The al fresco dining area is great for after hours lounging, the freshly squeezed all natural juices good for the taste buds, and the location in a quiet part of the middle of it all absolutely sublime.
Southernmost Beach Cafe. This may be a traditional tourist spot, but who could blame you for ordering your conch fritters where, when the sunsets are so magnificent? We didn't make a reservation but we like to eat late—which suited the restaurant perfectly.
DJ's Clam Shack. If you go to the Keys and you don't like seafood, you might as well turn around and head home at dinner time because the excellent fish, mussels, and conch dishes are truly a gem. I only have three food suggestions for DJ's: lobster roll, fried shrimp, and sangria, and one general warning: this has become a bit of a hotspot so go while the hunger pains are still far away because you might have to wait to snag one of their precious tables.
What To Do
Hemingway House. My fondness for Ernest runs deep, even deeper than his palatial in ground swimming pool, which you can see with your own eyes in a tour of his house and grounds. True, it is always teeming with tourists (and everyone will tell you to skip it for a visit to the unmarked Tennessee Williams homestead), I love getting a chance to photograph and love on the hundred or so six-toed cats instead, and nothing beats a walk around the second floor backyard writer getaway.
Fort Zach Beach. Known to the rest of the world as Fort Taylor Beach, this southernmost strip of beach is where all those colorful fish come to hide from the fisherman. A great place to take a beach walk or to swim out to the rocks for a dive with the critters, Fort Zach is also a little 10 minute walk from Duval House, making it more or less the perfect way to spend the first day (or the first five days) of your vacation.
Mallory Square. True, this is another thing tourists love, but how can you resist one night of sipping fresh juice out of a half coconut shell and watching the sun go down as street musicians serenade you? What else is vacation for? You can also wander into the local market there, but be warned: it's full of shot glasses and trinkets made in China. For the for the good stuff, head down Duval for cool pieces by Key West Pottery.
Dry Tortugas. If you can spare an extra day to make the trek (since it does require, at the very least, a whole day), make a reservation to get to the Dry Tortugas—the real southernmost part of the US. The national park has a rich history, but an even better opportunity to visitors to snorkel. Or, if you've got the time and the skills, a 3-day boat charter to explore the area with dives is a great way to get acquainted with the fishes, the sand, and the sea.
What not to miss
Kermit's Key West Key Lime Shoppe. Ignore their annoying extra use of "e" and let your tastebuds take precedent because you're gonna want to take a taste of the Key Lime Salsa and stash a couple handfuls of the taffy for the trip home.
Garbo's Grill. Food truck extraordinaire. Ever since I went to New York I seek out excellent street food whenever and wherever I can. In the case of Garbo's Grill, you just can't get a better taco anywhere on the island, or probably in Florida at all.
Duval Drag. A couple of blocks down from the guesthouse is a little number where gals in tall heels, full makeup, and sequined dresses resist the heat, and there's no better show on the island. For fans, you can catch nightly exhibitions at 801 Bourbon Bar. If you're a newbie to the scene, simple stroll down Duval in the late afternoon...you'll get a slice of the island nightlife that way too.
Key West Cemetery. The epitaphs are just as jovial as the island citizens who rest here; only in the Keys could you stumble upon a self-proclaimed Julio Iglesias lover laid to rest in the loamy soil. Other honorable mentions: "I'm just resting my eyes" and "I told you I was sick."