Right when I spotted a rooster roaming around Key West’s miniature, two-gate airport after walking off the plane on the open-air jetway, I began to understand why everyone I asked about the island described it only as “interesting.” Needless to say, it was obvious from the beginning that Key West is unlike anywhere else I’ve ever been.
“Interesting” isn’t necessarily negative, but everyone’s forewarning tone, smirking smiles and refusal to elaborate piqued my curiosity. After all, I was only in search of someplace warm with good food to spend my birthday. And that’s how my boyfriend, Kyle, and I found ourselves spending a week of sun and celebration in Key West, sipping cocktails by the beach while roosters crowed nearby.
Yes, roosters are everywhere in Key West, including the island’s only private beach at the Casa Marina Resort, where we stayed. Along with the brightly-colored birds, cats freely wander the island, welcoming themselves into restaurants, perching right on the seats of tables as if to order a cocktail like the rest of us. Some cats are direct descendants of Ernest Hemingway’s beloved pets, distinguished by their six-toed paws — although I never actually counted to confirm.
Key West’s complicated culture is, I think, because it’s a place of so many contrasts. The tiny island (it’s barely seven square miles, most of which is recently-added landfill) is so well-known that it feels larger, despite being able to walk the island from end to end in half an hour. It’s enormously touristy, yet has a distinct small-town feel to it. Majority of the restaurants are locally-owned places serving local catches. It’s definitely a party city, yet knows how to relax and take in the simple pleasures of life (Key Lime pie anyone?). And everyone is welcome. There are retired tourists, young families, wild middle-agers and everything in between, strolling the streets next to drag queens.
We spent our week in a rhythm that mimicked the waves: out into Old Town, back to our hotel, then out to Old Town, and back to our hotel. Our mornings started at French cafés (they are everywhere on the island) eating breakfasts of Croque Madames, crepes or lobster Eggs Benedict, before returning to the hotel to soak in the sun at the beach.
We sipped on summery cocktails (I’m convinced that nothing completes a day at the beach like a piña colada) desperately soaking up as much warmth as possible, not believing that it is still winter. (Then again, winter in Chicago is quite a contrast.) When we got hungry, we ordered conch fritters — deep-fried balls of chopped conch meat and green peppers in a batter, served with aioli — a culinary tribute to the island’s Bahamian influence.
By evening, we walked to Old Town in search of seafood and sunsets. Key West is known for both, and combining the colorful skies with the island’s signature shrimp, lobster or Cuban food was a nightly highlight. For such a small city, its food culture is enormously prominent and the pride in which restaurants serve these dishes is obvious by how good everything tastes. (More on what to eat in Key West later.)
We ended every meal with key lime pie, the island’s most popular export and coincidentally my favorite kind of pie. What constitutes authentic Key Lime pie, besides being made with local key limes, is fiercely debated; some argue meringue must be on top, others firmly vote for whipped cream. To be fair, we tried both ways. Plus chocolate-covered slices, Key Lime pie in cocktail form, even one served in a jar. (Stay tuned for the best key lime pie in Key West.)
Finally, we ended each night back at the Casa Marina, lounging at the beach-side bar or swaying in the trees in a hammock, listening to the waves while rehashing whatever weird things we saw that day.
On my birthday Kyle surprised me with a sunset dinner on the private island, Sunset Key, only accessible by ferry. We ate an amazing meal of grilled lobster and wagyu steak while we watched the sun slowly slip into the ocean, then finished with an incredible slice of sparkling key lime pie. It was the most wonderful celebration of my birthday I could imagine.
When we first got to Key West, I couldn’t imagine ever returning after this trip. But by our last day, the interesting culture had worn on me. I’d fallen for the quirkiness, the incredible food, the colorful architecture, the laid-back atmosphere, and even got used to the roosters. Now I can’t wait to return to try deep-sea fishing, snorkeling and the rest of the restaurants in town. And because I’ll never be able to eat another slice of key lime pie anywhere else.
P.S. Check out the Random Acts of Kelliness facebook page!