Read Caption
Sunset on Mallory Square in Key West (Photograph by Blaine Harrington III, Alamy)

Road-Tripping the Florida Keys

I set off from Miami without an agenda. I was headed south to Key West on the famous Overseas Highway and wanted to let serendipity lead the way. With only a short amount of time on my hands, I didn’t want to be saddled with an endless list of to-dos.

Here’s what I found on my road trip through this idiosyncratic island paradise:

> Coral Castle Museum

The drive from Miami to Key Largo is generally uneventful, but you can veer off and stop at the Coral Castle Museum, a roadside curiosity borne of one man’s brilliant eccentricity. Ed Leedskalnin reportedly spent 28 years of his life carving a palace made of coral–complete with a throne room, bathtub, telescope, fountains, gates, and a sundial–from the ground up after he was jilted by his fiancée a day before they were to wed. Even more unbelievably, it is rumored that Leedskalnin moved the massive limestone boulders himself–though he refused to allow anyone to watch him while he worked.

View Images
Ed Leedskalnin’s inspired masterpiece (Photograph by Annie Fitzsimmons)

> Card Sound Road

Thanks to a suggestion via Twitter, I decided to take a slight detour onto Card Sound Road to check out roadside joint Alabama Jack’s. This sweet southern stretch, dotted with reclining beach chairs and fishing poles, is the perfect way to get you into a Keys state of mind. If that’s not enough, the conch fritters and terrace overlooking the swampy mangroves at Alabama Jack’s, a place out of time that brings together an eclectic mix of bikers and beachgoers, will do the trick.

> Key Largo

Upon entering Key Largo from the mainland, I was faced with an onslaught of discount T-shirt stores and sandal outlets. After scanning for a compelling place to stop (and bypassing tempting signs for “world’s best” key lime pie) and coming up short, I decided to pop into the Key Largo Chamber of Commerce in search of some local advice. I thought about hopping on a glass-bottom boat cruise through the aquatic wonderland that is John Pennekamp Coral Reef State Park, but once I heard about the sea turtle rehab center an hour’s drive south in Marathon, I decided to book a tour for later that afternoon and find a place to grab a snack. And when I saw a sign for “famous key lime muffins,” I pulled into Harriette’s to taste a sweet treat made with the islands’ own brand of citrusy goodness.

> Islamorada

For me, Islamorada, composed of six small islands that market themselves as the “sport fishing capital in the world,” was the point where the natural beauty of the Keys began to take center stage (sunglasses are essential; my polarized lenses made the ocean’s brilliant greens and blues pop even more). I found the perfect view overlooking Whale Harbor Marina on the deck at Wahoo’s Bar and Grill, a place where your shoulders automatically loosen once you’re seated and the menu is full of delectable seafood caught a stone’s throw away.

> Marathon 

After my fascinating 90-minute tour of the Turtle Hospital, the first of its kind in the world, one thing will always haunt me: a photograph of all the marine debris that had been removed from a single sea turtle–including a shoe sole, hooks, and plastic gloves. Rehabilitators revealed other repeat offenders such as duct tape, bike tire caps, and balloons (I will never release a balloon again). Beyond threats from trash, in southern Florida, where boats are as ubiquitous as key lime pie, sea turtles are often struck by boats or damaged by propellers. Because their spinal cords are fused to their shells, this kind of trauma can be especially damaging–even fatal. After touring the operating rooms, you’ll get to meet some of the turtles being treated–and watch them swarm as you feed them tiny pellets of food.

> Seven Mile Bridge

Connecting Knight’s Key to Little Duck Key, the Seven Mile Bridge is the crown jewel of the classic Florida Keys road trip. Being that far from land on both ends is absolutely breathtaking, even a little bit scary. The only thing that would have made it better is if I had been a passenger (I’d have had more time to gawk). You can stop at tiny Pigeon’s Key, which housed the workers on the original 1912 bridge. Taking a page from New York City’s playbook, the Florida Department of Transportation has recently announced plans to restore the old bridge as a tourist destination in its own right a la the wildly popular High Line.

Tip: After the bridge, stop at Bahia Honda State Park to visit Calusa Beach, one of the most picturesque stops in the Keys, adjacent to the old Bahia Honda Bridge.

> Key West

I caught the beginning of the sunset in lively, packed Mallory Square, and then watched the rest from Sunset Key, a tiny island a few hundred yards off the coast filled with ritzy pastel cottages outfitted with front porches and Adirondack chairs. With no passport required, it feels as if you’ve traveled many more miles for a tropical getaway. You can stay on the private island, at Sunset Key Guest Cottages, but regardless of where you hang your hat, I recommend taking a boat over for the best view in Key West, followed by a meal at the resort’s restaurant, Latitudes.

Back on Key West proper, I strolled hit-or-miss Duval Street and found great salad and sandwiches at casual Panini Panini before touring the Ernest Hemingway House across from the Key West lighthouse. You can’t miss the 50-odd six-toed cats (descendants of felines owned by Papa himself) that roam the charming property. Save time for a stroll around Old Town with its quaint homes, roosters crowing, and the South Florida heat warming the sidewalks.

Annie Fitzsimmons is on the beat exploring some of the sunniest places in America. Follow her adventures on the Urban Insider blog, on Twitter @anniefitz, and on Instagram@anniefitzsimmons.

> Related: