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Conquering the quieter side of Key West

Karla Hawkins ducks beneath mangrove trees during a two-hour guided tour of Key West’s backcountry waters.NICOLE CAMMORATA/GLOBE STAFF/Nicole Cammorata

KEY WEST, Fla. - When I tell others I’m planning a long weekend trip to Key West with a friend, there’s a response that has become so predictable, I begin to say it with them: “Wooo spring break!’’

Undergrads between classes we are not. It is the sunshine and Key West’s island vibe that call to us.

While there is an almost constant party atmosphere on Duval Street, it’s not the only thing this island has to offer. There are many attractions to fill one’s time: beaches, restaurants, beautiful houses, museums, and especially, kayaking through the quiet back country.

But first, to the bars. My friend Karla and I sip mojitoes and coconut-flavored rum at the Lazy Gecko, which bills itself as the “Southernmost Red Sox Nation,’’ a superlative shared by many establishments on this outpost. We end the night next door at Sloppy Joe’s, where we pay homage to onetime Key West golden boy Ernest Hemingway.

The island is small - only about 2 miles by 4 miles - so instead of a car, we rent bikes. We wind through the sleepy streets on our way to the beach, with towels and sunscreen stowed in baskets hung from the handlebars. Biking Key West is the way to go. Although it is crawling with tourists fresh off the cruise ships that dock near Mallory Square, it’s immensely walkable and bike-friendly, with bike racks always open.


The morning after our bar crawl, we are headed for kayaking out of the Hurricane Hole Marina, a place best reached by car. Lucky for us, the folks at Lazy Dog Kayak Guides offer free pickup and drop-off. We’re out the door early, determined to discover a different side of the island.

Karla and I sign papers (of a “you-can’t-blame-us-if-you-die’’ sort), board our double kayak, and with a quick shove from someone on shore, we’re off.


As the more experienced paddler, I sit in the back to steer while Karla keeps pace up front. She’s a worthy paddler and we leave the confines of the marina and slip into the clear, shallow backcountry waters.

The guided group tour, which lasts about two hours, is for a wide range of skill levels. There are nearly two dozen people in our group: a 60-ish woman paddling solo, family groups, couples, and a surprisingly patient man with a 7-year-old who needs tips on steering. (If you want to turn left, plunge the blade of your paddle into the water on the left side of the boat . . .)

Guides Bethany McColley and Kelly Mack take us through the rippling waters. It’s a windy day and we’re fighting against the pull of the tide on the way out. We hug the shoreline of a series of small islands, stopping for the occasional ecology lesson.

McColley corrals us by the trees, plunging her hand into the water and producing a sea star - what most people know as a starfish. We circulate the echinoderm as our guide describes the sea star’s skill of limb regeneration. Farther along, we pass around a sea cucumber (slimy), a conch (heavy), and then peer into the water gazing at sea sponges in their natural habitat (they are bigger than you would expect).

The conch is the de facto symbol for Key West and can be found on menus throughout the island in the form of conch burgers, fritters, and chowder. Overharvesting of the mollusk over the years has threatened to wipe it out, which is why it’s now illegal to take them from the water. The conch you eat here comes from the Bahamas.


In 1982, the people of Key West symbolically seceded from the United States, dubbing themselves the micronation of the Conch Republic. These days, it’s a source of pride as well as a tourism draw. A person born on the island is referred to as a conch. Someone not born in Key West but who has lived here for at least seven years? A freshwater conch. A student at Key West High School is a fighting conch.

Before heading back to the marina, we scoot into a cave-like enclave formed by the boughs of a mangrove, the gnarled branches of this saltwater tree dripping back into the water where it will send out new roots into the seafloor. These groves are uninhabited, as there’s not much to stand on save for a disconnected labyrinth of tree roots. They cut the wind though, and our guides tell us they make an excellent refuge during storms. Our rambunctious group maneuvers around each other, the occasional bumper boating incident inevitable as we back out of the grove. After a leisurely paddle through a bit of open water, we duck into another set of mangroves that forms a sort of tunnel over us before we emerge back at the marina.


Lazy Dog also offers a snorkeling and kayaking combo tour, as well as paddleboard yoga, which is is exactly what it sounds like: sun salutations and warrior poses while balancing on a board atop the water. I am intrigued, but we don’t have the time. Instead, I vow it will be at the top of my list when I return. That’s the thing about Key West - you’re planning your next visit before you’ve even left.

If you go...

Lazy Dog

5114 Overseas Highway

Key West, Fla.


Two-hour guided kayak tour $35.

Nicole Cammorata can be reached at