With a bit of exploration, I quickly learned that the Keys have more personalities than Sally Field in the 1976-made-for-TV movie “Sybil.” There’s the sporty Key Largo, the arty and fishy Islamorada, and even a tiny island off of Key West that is gaining a reputation for becoming Brooklyn to Key West’s Manhattan. I haven’t fully bought into that one yet. What I’m getting at in my usual circumlocutory manner is that whatever you’re looking for in the Keys, you can probably find it as easily as iguanas or conch fritters. Which Key is for you? Fasten your seatbelts. We’re going for a ride.
KEY LARGO: Scuba and snorkeling
I previously thought of Key Largo strictly as a mile marker, reminding me I had two more hours in the car until I hit Key West. Also, as the name of a 1948 movie and the title of Bertie Higgins’s milquetoast 1981 easy-listening hit. But this Key refers to itself as the scuba diving capital of the world. It has the third-largest barrier reef in the world, along with John Pennekamp Coral Reef State Park, home to the oldest underwater preserve in the United States. If you’re going to jump into the water, this is the place to do it. I long assumed Key West was the largest Key, but Key Largo holds that distinction.
I sought a different way to get onto the water in Key Largo. I took a trip on a 111-year-old steamboat that is on the National Register of Historic Places. The boat was also the title character in the 1951 Humphrey Bogart/Katharine Hepburn “The African Queen.” Through a random series of events that would require a very long explanation and an expansive attention span that I do not possess, the African Queen is now docked in the Keys and takes tourists through a canal system in Key Largo for $59.
The affable African Queen tour guide peppered me with movie trivia questions, first about “The African Queen” and then other movies. Typically there are six people on the boat to volley back answers, but because it was freezing cold by Keys standards (68 degrees and windy), I was the only one brave enough to board. I learned a lot about Key Largo and also learned that I don’t know much about movie trivia.
If you opt to take the African Queen tour, I advise you seek sustenance for the voyage at Harriett’s Restaurant with biscuits and gravy. The biscuits are the size of a toddler’s head and flakier than Christopher Lloyd. For lunch or dinner, head to the Fish House. The conch is pricey at $37, but worth it. The advantage to staying in Key Largo is that hotels are much less expensive. Waterside Suites and Marina has large rooms with kitchens and laundry starting at $250 a night. You will not find a 600-square-foot suite in Key West for $250 a night. There are plenty of more affordable options if you’re looking for a getaway on the cheap.
ISLAMORADA: Fishing and toilet seats
Before I traveled to the Keys, I consulted with Ashley Serrate, who works in tourism for the region. She described Islamorada as “the up-and-coming cool kid on the block” thanks to its burgeoning arts district. There are more than a dozen galleries in town, although I’d classify some of these galleries as gift shops. But for the moment, Islamorada is better known as the sport fishing capital of the world. You’re more likely to snag a fish than purchase a painting of one. According to the website Fishing Booker there are more than 200 charters available on the Key to take anglers out for full or half-day trips.
But there’s another art installation in town. If you want to impress, or disgust, your friends, this is the gallery for you! Welcome to beautiful Toilet Seat Cut. It’s a waterway where each of the channel markers is adorned with personalized toilet seats. Call it folk art, call it tacky, or call it the most Florida Keys thing you’ll ever see. Where else on the planet can you kayak or paddle board alongside 250 hand-painted toilet seats? Hopefully the answer to that question is “nowhere.” The folks at Paddle the Florida Keys (paddlethefloridakeys.com) can set you up with a rental and instructions for seeing the best toilet seats.
I kayaked through the toilet seats, working up a sufficient appetite to justify a trip to Lazy Days restaurant where I dove into the fried fisherman’s platter (fish, shrimp, clams, and calamari). The food was good, the views were even better. The scene was lively in the beer garden at the Florida Keys Brewing Garden, which is located in Islamorada arts district, but not sadly not near the toilet seats.
Stopping by Robbie’s of Islamorada is required for feeding the monster tarpon, more kayaking (I paddled to the incredible Lignumvitae Key Botanical State Park), and then unwinding with a Trailer Trash Bloody Mary at the Thirsty Tarpon bar at Robbie’s. I’m no jock. I’m more of what you’d call an athletic supporter, but even I could manage kayaking on the calm turquoise waters of the Keys.
DUCK KEY/MARATHON: Families and pie fanatics
Once you hit the mid Keys the scene becomes a tad less adults-only and more family-focused. What I’ve sorely neglected to mention is the diversity of lodging options in the Keys. The Keys don’t offer much in the way of beaches, so if you’re traveling with kids who require time to splash around, I advise looking for a resort, or at least a nice hotel or Airbnb with a pool.
There’s even a resort on Duck Key called Hawks Cay that has a child care center where you can dump the kids — I mean drop off your precious little ones — while you go to dinner or engage in other grown-up fun. Hawks Cay is a posh resort that is still less expensive than most hotel rooms in Key West, but offers several pools, pickleball courts, kayaks, and a sandy lagoon. It also has a restaurant called Angler and Ale that was recommended to me by people who know food, and you don’t need to be a guest to eat there.
Hawks Cay was my Florida Keys indulgence. I stayed at a few places in the Keys that I wouldn’t recommend, so the resort was a lovely palate cleanser between honky-tonk lodgings. Sheldon Suga, the managing director of the resort, said it’s designed for people who want to simply unpack and relax. There’s a full itinerary of activities every day on site. The place even rehabilitates dolphins, and you can visit them.
Speaking of family and fish, nearby Marathon has the Turtle Hospital, Dolphin Research Center, Crane Point Museum & Nature Center, and Sombrero Beach, which is one of the few beaches on the Keys. The Turtle Hospital may not be as showy as the Theater of the Seas, but I prefer to look at sweet turtles recuperating over a woman riding two dolphins like a pair of water skis any day of the week.
Before departing Marathon, there was one more very necessary stop to make, and that was Burdines Waterfront restaurant. This was where I found a true marvel of American ingenuity: fried Key lime pie. The restaurant makes Key lime pie, freezes it, and then wraps it in dough and quickly fries it. It’s hot and cold, sweet and tart, and it comes with a side of sunset views.
THE OLD SEVEN MILE BRIDGE: Walking and history
It’s not a Key, but the newly-restored Old Seven Mile Bridge is worth a stop to soak in the many shades of blue shimmering below. Only 2.2 miles of the bridge have been restored. It ends at Pigeon Key, where you can see some of the historic structures that housed the workers who built the original bridge for Henry Flagler’s overseas railroad at the turn of the last century. Whether or not you visit Pigeon Key, the bridge is still a gorgeous walk.
Big Pine Key: Nature
This stretch of the Keys is the only place you can find the endangered Key deer. They are the smallest of the white-tailed deer family, and, in my estimation, the cutest. Stop at the National Key Deer Refuge and the very friendly staff will give you a map and show you the best places to find them. I followed the map and instructions to the letter, and I only saw a few alligators. All was not lost! As I was departing Big Pine and driving to No Name Key, I spotted a Key deer grazing in someone’s front yard. Perhaps the deer was tired of getting gawked at by tourists and just wanted to eat in peace.
KEY WEST: Get your freak on.
It was the end of the road, and the beginning of the debauchery. Duvall Street is like Bourbon Street South, with some of the best people watching this side of the Mason-Dixon Line. The beauty of Key West is that there are options for fine dining (Little Pearl, Cafe Marquesa) or places to cringe through a meal (Hard Rock Cafe, Jimmy Buffett’s Margaritaville Key West). My favorite times have been when I’ve gotten lost and found great little shops (Key West Island Bookstore) or fun bars filled with locals (Bobby’s Monkey Bar). You don’t need me sending you off to see the sweet cats at the Hemingway House or the Museum or the Truman Little White House. What you need is a couple of days to make your own discoveries and create your own list of favorites. My trick is that I find these local haunts in Key West, and then don’t share them with others (like you, dear reader). That way they’ll always remain my personal unicorns.
Christopher Muther can be reached at firstname.lastname@example.org. Follow him on Twitter @Chris_Muther and Instagram @chris_muther.