The Optimistic Traveller

The Key to Key West

The first time I visited Key West as an adult, I felt naughty,

It was right at the beginning of the White House transition in 2001, and I had to get in the vacation time while the weather was still justifiably crappy in DC. Plus, my Continental Airlines (remember them?) travel voucher was about to expire. I got a lot of shade for the decision (from no one I cared about, i.e. the President or sweet colleagues like Betty), but I needed a break and had always wanted to return to the place I vaguely remembered driving and camping through with my family at 6 years old.

I was excited to learn, when I called, that the little island, accessible only by tiny puddle jumper, was considered part of the “continental U.S.,” in terms of the airline’s volunteer free voucher policy, that is.

Ben and I were already massively in debt, mainly from eating out all the time, and I’d been gaining weight from late Taco Bell nights at the very end of the Administration’s term; I’d been  working later hours and would continue to put in long days until the move to New York at the end of the summer.

But off we went, and from the moment we arrived it felt like we were, indeed, on an island somewhere south of the US. The vibe was distinctly tropical, with live music in every other bar, Pride posters and men holding hands, and descendants of Hemingway’s polydactyl cats roaming everywhere, cutely and expansively. The Hemingway Home was a neat excursion and a taste of Havana, where the writer had spent the other half of his time. It would be more than twenty years before I was to see THAT city, and now that I have, I can see why Hemingway liked both.

Duval Street was (and is always) lively as hell, given we hailed from the Courthouse area in Arlington, Virginia, a quiet little suburb across Rt. 50 from Fort Myer. When we “went out” on weekends, I really let loose and put on glittery eyeshadow. It was a big deal. So, Duval Street might as well have been the French Quarter or the Lower East Side.

Our little hotel had a pool and a happy hour meant for mingling, but we stayed to ourselves. We were walking distance to most everything and quickly found Half Shell Raw Bar and gorged ourselves on oysters and huge Gulf shrimp. That place remains one of my favorite eating establishments in the world. I’ve taken my friends there on a girls’ trip, my mother, my son, and my husband numerous times. The raw bar is still just as good as it was 25 years ago, and the décor just as tacky and appealing, with license plates from all over the world on the walls and retro style “Eat it Raw” t-shirts for sale, emblazoned with 50’s pin-up model graphics.

There are plenty of great restaurants in Key West. One of my favorites, Azur, is tucked away from the hubbub and has a wonderful brunch and a patio area. Old Town Mexican Café is conveniently located and delicious, with plenty of outdoor seating and, usually, live music.

Of course, you simply must eat key lime pie, key lime ice cream, and anything else key lime you can get your hands on while you’re there. Kermit’s shops always have samples of everything, from cookies, to cheesecake, to weird things that (possibly) shouldn’t be flavored with key limes.

On that first trip, there were some good thrift stores still in business, but that scene is limited these days. I broke a shoe on one trip and was compelled to purchase uncomfortable designer flipflops for over $50. There are no longer real bargains to be had there, but there are some very cute boutiques, nonetheless. You’ll find stunning swimsuits and breezy dresses and elaborately-beaded Mary Frances bags at shops catering mostly to wealthy tourists. Near the port, there are some historical sites and an old building converted to host a variety of shops, including Boutique Alexandra, which sells a hodgepodge of items, including perfumes, home décor, and vintage items. I bought a couple of old metal Dutch figures for a song there, but mostly, it was a nice respite from the heat and a fun place to peruse.

Thankfully, the huge coral reefs off of Florida have been better regulated in recent years than they were back then, when sewage was flowing right through them. Fun fact: Katie, my college roommate, was one of the scientists to discover and isolate the bacteria attributable only to human feces. But I most disgustingly digress.

The snorkeling was nonetheless incredible, poop and all, and we stayed out for a long time, the barracuda and I practically eyeball to eyeball, as they were attracted to my jewelry. It is an odd surprise, and momentarily alarming, to turn and suddenly be that close to any creature, especially underwater. I’ve become habituated to it over the years. The visibility that day was fantastic, and it was my first time really snorkeling, and I was proud of myself. A snorkeler was born. When we got back on the boat, a delicious fried chicken lunch was served, and to this day was one of the most satisfying meals I’ve ever had. The ever flowing Mai Tais and rum punches were nothing to sneeze at, either.

Wicker Guesthouse is a cute place to stay right on the far end of Duval near the Hemingway House. It has a lovely, secluded pool in which I once swam with a number of young, inebriated men who, the more they drank, the more they seemed enamored with me. (That’s a story in another column.) Breakfast is included, but there are also cute coffee and smoothie shops right nearby. Each room has its own little porch or balcony and is individually decorated.

Heron House is on the opposite side of the island, closer to the Atlantic than the Gulf. Billed as an adults-only B&B, it has several reading nooks and is generally quiet and peaceful, with well-curated plants all around. It is also just a hop from Half Shell and the port to get snorkel boats, and right around the corner from the aforementioned Azur restaurant, where I had one of the best and most beautiful Nicoise salads ever, even comparing those eaten in Nice.

What child of the 70s and 80s and beyond didn’t grow up reading Judy Blume books? Having read her right alongside Hemingway, Key West now seems like a writerly destination. The bookstore Blume co-owns there is actually a non-profit, part of a cultural arts center. I haven’t gotten to meet her (yet), but apparently she frequents the place and signs her books for patrons, unassuming and kind. She’s a local hero, like Anne Patchett in Nashville or Billy Joel throughout Long Island (and possibly Allentown, PA). Those yesteryear memories of Key West and its mosquitos and unbearable heat, the Coleman stove and oranges bought for pennies on the side of the road on the drive down…well, they have their place. But Key West is better than that. My version has developed over many visits: tropical vibes, skimpy attire, love, good food, and a beautiful place to commune with sea creatures; a place to party, a place to reassess and start again.