Few places in America have inspired as many stories and songs or solace and sin as the Florida Keys. Made up of 800 islands spread over 180 miles, the fabled region has served as Native American burial grounds, a pirate hideout, the gateway to Havana, a Cold War military hotspot, and a source of inspiration for storytellers ranging from Ernest Hemingway, to Jim Harrison, to Tennessee Williams, to Bob Dylan, to Jimmy Buffet, among many others. Not to mention, all the Florida Keys stories lived and gone untold.
On a trip to Key West ten years ago, I met a Clemson spring breaker who is now my wife. To celebrate a decade since our chance encounter at a Duval Street bar, we loaded up an Airstream along with our two kids, and headed off on a pilgrimage to the Conch Republic.
Here’s a journal of our trip as a starting point to help you find your Keys story. You never know, it just might change your life.
Prologue: The Palm Coast
I had never towed so much as a lawn mower before this trip, let alone a 5,000-pound, 22-foot Airstream Caravel. Our chariot of choice was a new Ford F-150 PowerBoost (aka hybrid), knowing it could pull more than double that without crushing us with gas stops.
On our first night, we landed in the Palm Coast, at the beachfront Flagler-By-The-Sea Campgrounds, a small family-run spot where we were initiated into the social side of camping life when multiple men eyeballed our first parking attempt and came over to offer advice:
“When in doubt, just put your hand on the bottom of the wheel and move it where you want the trailer to go.” At any given moment, these men are sitting in folding chairs at campgrounds across America, just waiting for the chance to offer a few pearls of RV wisdom. So, it’s always a good idea to keep cold beer on hand with which to thank them.
Day Two: Key Largo
After a night of heavy sleep thanks to the sound of crashing waves through the open windows, we headed down a green stretch of I-95 through the Space Coast, before getting on the Florida Turnpike to make a run for The Keys. After a long day on the road, we turned off the Overseas Highway into Baker’s Cay Resort in Key Largo, a lush retreat of white walls, hidden walkways, and an explosion of palms, bamboo, and banyan trees, all oriented around an intimate cove with a private dock and white sand beach.
We found two empty chairs at a tiny hidden beach amidst the mangroves, and waded out into the salty, ankle-deep water, before ending up at the beachfront bar, Dry Rocks, for queso and margaritas. Night came with a sudden dark tranquility, and we sat on a balcony overlooking the beach, marveling at the fact that we were only an hour from Miami.
Day Three: Key Largo to Marathon
Just minutes from the heart of Key Largo is John Pennekamp Coral Reef State Park. Best-known as a snorkeling destination, a 4,000-pound bronze statue of Jesus, “Christ of The Deep,” awaits passengers on the many daily chartered snorkel trips to the reef. Instead, we pumped up our paddleboard and explored the clear mangrove swamps on our own.
The Airstream’s outdoor shower and wide awning made for the perfect temporary base camp. After a minor parking meltdown to stop at a Tacos Jalisco food truck we set up camp at Jolly Roger RV Resort on Grass Key, at a spot on the sea wall a few feet from the water.
Morada Bay on Islamorada was our dinner destination: an open-air bar and restaurant spilling out over a sprawling white sand “dining room” with tall palms angling up out of the sand, and a gleaming vintage Airstream for an accent piece by the bar. Our early reservation meant we’d miss the sunset, but we’d also miss the peak of the crowds––which were on our heels. Tuna Takaki, fried “Keys Pinks” shrimp tacos, and grilled local fish were standouts in one of the best meals of the trip.
Day Four: Cayo Hueso
The Turtle Hospital on Marathon Key was our first stop of the day. Housed in a former motel and a former gentleman’s club, the hospital takes in sea turtles who’ve had a close encounter of the shark tooth or boat propeller kind, and other such ailments, and either nurses them back to health to return to the wild, or gives them a place to live out their days in peace.
We finally hit Key West that afternoon, and landed at our home for the next two nights: The Perry Hotel, on Stock Island. The location just North of the heart of historic Key West was ideal, because it was easy to drive into the heart of the city, but just as nice to drive back out for some quality social distancing. The Perry staff are friendly and cool, and the Marina-fronting pool was an incredible place to soak up the sun, watch the marina traffic come and go, and poach the happy hour menu.
That night, a seafood hankering led us to the dockside Half Shell Raw Bar. This sprawling restaurant and bar is open to the air, which flows from the docks to the row of Harleys parked out front. The walls are covered with old license plates, mounted sailfish, life preservers, and vintage signs.
The happy hour is generous, the raw oysters and coconut shrimp were great, but the atmosphere was the star of the show. When I’m the tourist, I want to feel like I’m stumbling into a scene, not that I am the scene. And this place makes you feel like a fly on the wall instead of a fly in a trap.
Day Five: Mile Marker Zero
At 9 a.m. there was already a mob waiting out outside French Bakery La Grignote. I can’t stomach the site of people waiting in line for brunch, so I elbowed past them, on a hunch that I could order to-go at the register inside. Five minutes later, I emerged victoriously with incredible French pastries and supersized lattes. After devouring the croissants and cream tarts, we walked a block to find another line of people waiting to take pictures at the famous Southernmost Point marker.
We avoided this line by snapping a picture across the street, then we headed into the Butterfly and Nature Conservancy, a mystical (if humid) atrium filled with butterflies and birds, including a flamingo couple named Rhett and Scarlett. (It was mating season, and he seemed to give a damn.) We got a fresh coconut and a smoothie at The Raw Machine, a juice bar in an old Airstream which, like most places in The Keys, requires a bit of patience.
After a snack at Fisherman’s Café, we braved the Key West Shipwreck Museum, a creepy, confined, and vertical space that smells like old wood and has a haunting feel that a cosplay yarn spinner and a hologram-faced pirate only amplified. Getting up to the top of the rooftop tower is a little Vertigo-inducing, but you’re rewarded with sweeping views of downtown Key West and the surrounding waters.
Touristed out, we headed back to Stock Island and picked up lunch from Cuban restaurant El Siboney––Queso Frito, a Cuban sandwich, rice and beans, and coconut shrimp. I loved El Siboney’s downtown location a decade before, and it was just as good this time around.
That evening, our Keys pilgrimage culminated with a chartered sunset sail on the 38-foot sailboat, Don’t Blink. Bluesail Charter operates out of the Stock Island Marina, and while they have massive catamarans in their fleet, we opted for a more intimate outing.
At the helm of the boat was owner Scott Mayer, a Chicagoan who gave up corporate life for The Keys and never looked back. My wife and I drank Dom from the bottle as the sun set, toasting my late father, who was the reason for that Key West trip a decade ago. By the time we tied up back at the Stock Island Marina, we felt like we’d known our captain for years.
That night, we ordered dinner from Matt’s Stock Island: tuna tacos, crab beignets, fried chicken, and the best Key Lime Pie of the entire trip. We ate it on our poolside table, looking out over the silhouettes of palms, the mirrored surface of the pool, and the lights of the yachts in the marina.
For the Next Trip to Mile Marker Zero…
Day Six: Islamorada
Before leaving Key West, we had breakfast at Blue Heaven, known for their banana bread and seafood Benedicts. It’s an outdoor jungle of a restaurant where chickens and roosters roam free and eat crumbs from the tables, there’s live music most days, and a very cool tiki bar and one interesting outdoor shower.
After discovering five-toed cat prints all over the bumper of our airstream, we hitched up and headed back North to Islamorada, which is the only place other than Key West or Baker’s Cay that I felt would be worth dedicating an entire trip to.
I met a parrot, toured the brewery, and tasted a killer flight in the shaded outdoor beer garden at Florida Keys Brewing Company. Afterwards, I picked up some snacks at the Trading Post Grocery, run by the same family since 1966.
It’s a time warp of a place that makes a lot of its prepared food in-house, like chicken salads and Key Lime cake. Behind the store, we stumbled into one of the best meals of the trip at Bad Boy Burrito, with a menu ranging from burritos, to burgers, to sushi. While excess of menu diversity can usually be a red flag, everything we ordered spot-on.
We spent our final night in The Keys at Islamorada’s circa 1946 Cheeca Lodge, an ultra-luxe ocean-front lodge with seemingly countless swimming pools and tiki bars, and our spacious ocean-fronting room in the lodge had an outdoor tub overlooking the water. Islamorada is the sport fishing capital of the world, and as the host of its own annual Sailfish tournament, Cheeca feels like equal parts five-star-luxury and Hemingway-esque fantasy.
Day Seven: Leaving the Keys
Before our bittersweet departure to the mainland, we caffeinated at Café Moka along with homemade French pastries and avocado toast. One of the longest driving days of the trip followed, and we made it back to Flagler-By-The-Sea at sunset for another oceanfront Airstream sleepover.
Epilogue: St. Augustine
The sunny morning drive up highway A1A along the beach, from Flagler to St. Augustine, was one of the most scenic stretches of the trip and certainly the least-expected: water views interspersed with rich green flora, with seafood shacks and an old hardware store serving as reminders that Old Florida still exists, if you know where to find it.
I didn’t expect one of the best finds of a trip to Florida would be a South African grocery, but St. Augustine’s Fresh Market Island was the kind of diamond in the rough you dream of finding on a road trip. The dry sausage hanging on a rack let me know it was the real deal. We bought a prime steak, South African Wine, a fresh baguette, a spicy-as-all-hell chicken salad and a quiche made with South African sausage.
I finally understood what the Airstream experience could be in the forested privacy of the North Beach Camp Resort. Our corner site was surrounded by walls of palmetto and shaded by oak trees. I cooked our wagyu strip over charcoal just before a rainstorm.
We drank cocktails by candlelight under the awning, in the rain. We slept with the windows open, and woke up to the sound of raindrops on the palms and thunder in the distance. After fortifying ourselves with double espressos and South African quiche, we broke camp for the last time.
As I pulled out of the first back-in job that I’d nailed on the very first try, I remembered the men in the folding chairs who’d schooled me just a week earlier. And I knew they would be proud.