When traveling to Key West, Fla., don’t over pack. I planned for three outfit changes per day, plus shoes. Huge mistake! I was in shorts and a bathing suit every single day and so was everybody else. The fabulously chill vibe was established immediately at The Perry Hotel Key West on Stock Island, a welcome distance from touristy Duval Street.
Still, a 20-minute shuttle service leaves every hour, running from the hotel to many of the main island’s hot spots like Mallory Square and Smathers Beach (the hotel also offers bike and moped rentals for those who want more freedom to explore). I ventured down to Duval Street a few times to try key lime pie, pay homage to Ernest Hemingway (and his progeny of six-toed cats), catch the sunset at Mallory Square, eat more key lime pie, take the requisite selfie by the “southernmost point of the continental U.S.” marker, and savor yet more key lime pie.
If you’re like me and come to the island (mistakenly) believing you aren’t a fan of key lime pie, you still must try it in Key West. It’s practically compulsory. I tried varieties of the local delight at Matt’s Stock Island, Kermit’s Key West Key Lime Shoppe, Blue Heaven, Moondog Cafe & Bakery, Mattheessen’s, and Sarabeth’s. (If you’re keeping track that’s six slices in four days.) All were deliciously tart and sweet, but my personal favorite came from Matt’s Stock Island Kitchen and Bar: it was more custardy, with a coconut macaroon crust, and served in a jar, with graham crackers for dipping! (See below.)
Everyone goes to the Ernest Hemingway Home and Museum, and for good reason. Sure, you can walk through the beautiful Art Deco home and gardens on your own, pet the six-toed cats, and pick up something at the bookstore—but my advice is to take the free guided tour (tips are accepted) for the anecdotes alone. You’ll get the backstory on the contentious swimming pool and bathtub in the backyard, and you’ll learn the cats’ names and the legend behind their extra toes. Fifty feral felines roamed the property when I was there, all direct descendants from those owned by Big Papa himself.
If cats aren’t your thing, and you prefer cocks, head to Old Town. There are cocks everywhere here. Roosters randomly strut down the sidewalks and streets, interrupting traffic to show off their swagger and sexual prowess. Colloquially, the feral Key West fowls are called gypsy chickens and their presence is very benign, matter-of-fact, and legally protected — albeit a bit noisy.
The ambiance was perfect at The Perry Hotel, named after Commodore Matthew C. Perry who claimed the Florida Keys as U.S. soil in 1822. The industrial-chic Perry Hotel is quirky, beautiful, serene, and airy. My enormous and comfy king-sized room with balcony overlooked the pool and had a view of the adjacent Stock Island marina, which serves as an anchor to the former shrimp-packing warehouse and offers an amazing “boat-to-table” experience at the open-air Salty Oyster Dockside Bar and Grill and Matt’s Stock Island (where the stone crabs were meaty and succulent). I had most of my meals there with the exception of the must-order lobster tacos at the Fisherman’s Café. Winter is prime pink shrimp season so the sweet and tender servings were very generous. I’m not quite sure what was in Matt’s Fish Dip, but damn, it was the most near-perfect thing I have ever put in my mouth.
The Perry concierges went above and beyond to help me arrange activities and were savvy (and insistent) enough to make sure I built in plenty of time to eat and rest. They also provided bottles of water to stay hydrated “because even if you’re in the water, you’re not absorbing any of it.”
I opted to do a backcountry kayak tour with Key West Eco Tours. A shuttle from Perry dropped me and off at the Geiger Marina, where our nature guide led a small group on a super easy paddle through the mangrove trails, pointing out sea stars, hermit crabs, stingrays, baby sharks, and sponges. I held a sea cucumber that began inverting itself in my hand! It was two solid hours of splendid sunshine, education, and calm waters.
For a bird’s-eye view of Key West and 10 minutes of complete, utter splendor, I recommend parasailing with Sebago Key West, located on the Harborwalk. At heights of 300 feet above the water there’s a remarkable meditative stillness. The bustle from below fades away and all you hear is wind rushing through the sails. Bring a friend if possible, because if you go solo you won’t reach the same altitude. They paired me with a very sweet 16-year-old from outside of Philadelphia who happened to be celebrating her birthday. She didn’t mind being whipped around and we talked about how she wanted to be a writer — and I thought, I never did anything this cool when I was 16. Sebago provided instructions, secured our harnesses, and then eased us aloft. We requested a wilder ride, so they dipped us down toward the water a few times. You can purchase video and photos at the end of the hour-long (including boat ride) adventure.
I love Jet-Skiing. Key West Water Tours, a partner of The Perry, offered a guided Jet Ski tour a short walk from the hotel and I eagerly signed on. But I’m embarrassed to admit I had problems right off the bat. I couldn’t get out of the no-wake zone and found myself sandwiched between a shrimp boat and the dock. The guide who came back for me was patient, kept telling me to relax and to stop overthinking it, and he was right. Once I got out into the open water I got into it and was whipping around at 20-25 miles an hour. The only problem was I needed to be going 30-35 to keep up. Apparently, what I really love is being a passenger on a Jet Ski. I ended up worrying I was holding up the rest of the group and eventually, I signaled that I needed to stop. The guide was understanding and immediately called someone to escort me back. Driving a watercraft isn’t for me, but if you do want to try it, I recommend Key West Water Tours. Fortunately, even my epic water sports fail couldn’t put a damper on the magic of this uniquely beautiful island getaway.