Blowing Through the Lower Florida Keys
Story and photos by Tim Leffel

After Irma came through like an unwelcome guest and trashed the place, Key West has mostly moved on. Further north, the whims of the hurricane winds left damage that man and nature will surely push past, as they have over and over again.

Florida Keys travel

Rays swim by and a pod of dolphins follow us before we even get into the kayaks, then we paddle along the shallows and see sharks and horseshoe crabs. Cormorants fill the trees and an osprey squawks when we get too close. The mangroves that were gray and leafless after the storm are dotted with a carpet of light green from new growth.

Where the people live, it's a different story. Not five minutes before we had been on the shore of Big Pine Key, in a temporary office in the one section of the marina building that survived. The docks were trashed, flooded cottages now razed, one home still covered with tarps. When Hurricane Irma released her full wrath on the Florida Keys, it seems like nature was far better equipped to duck and cover, then recover.

The big tourism destination of Key West got lucky, I've heard, just feeling the edge of the hurricane, most of its buildings from the 1800s and early 1900s still intact. I'm a bit apprehensive as we come into port on the Key West Express from Fort Myers. Everything looks fine from a distance, but I've learned over the years that you have to get up close and hear the stories to know what really happened in the heat of battle.

A young man in a t-shirt shop tells us his shop had water on the floor after the building's roof started leaking and then a hole opened up in his ceiling. The bar a few doors down, where most of the seating is outside, was disassembled by the high winds like a toothpick sculpture. "A big crew of Mexicans with nail guns put the whole thing back up in a few days," he says with amazement.

A City Built on Mishaps

Key West historic home

Key West is used to booms and busts, high hopes and letdowns. They're accustomed to the kind of weather that comes from being in the tropics, just 90 miles from Cuba. In a way, the city owes its fortune to disasters. As both a port and a southern island near a barrier reef, it has long been part of a major shipping channels between the Caribbean, Mexico, and the continental USA. Through navigation errors or bad weather, ships frequently got stuck on the reef or capsized. The townspeople of Key West were close enough to row out to the ships and save the people and cargo-for a piece of the action of course. Less than a decade after the island officially became part of the USA in 1822, it became the wealthiest city in America per capita, continuously dividing the spoils of shipwrecks in a manner ordained by local court decrees.

As the local Shipwreck Museum explains it though, most of that opportunistic wealth came to an end once heavier steamships started charting a more predictable path. The city exported salt and sponges harvested from the sea until a hurricane destroyed both industries in 1876. Ten years later a fire wiped out 18 cigar factories and 614 buildings. Ever since, every home has to have a metal roof. Eventually some forward-looking government officials started making a push to promote the area as a tourism destination. That wouldn't happen for real until about a hundred years ago, however.

A lot can happen in a century and Key West is now a full-fledged tourist town, getting gay couples and Europeans, spring breakers and retirees. Duval Street gets loaded with sunburnt middle-aged suburbanites falling down drunk, many from cruise ships disgorging the latest thousands buying their XXL T-shirts with sexual innuendos.

Key West party bar

Still, this is a historic town that retains a surprising depth of character once you get a few blocks off the main drag. Many of the grandest old homes are stately B&Bs and in between are hundreds of homes still filled with local residents going about their lives.

The Highlights of Key West

As a writer I've got one pilgrimage site on my list: the Hemingway House. Ernest Hemingway spent his most productive years in this house so well-designed that it has a dry working basement. Ask a novelist to describe the perfect writing studio and you'd probably end up with Hemingway's, which was connected to the main building by a catwalk. He had multiple marriages, multiple accidents, and ended up taking his own life, but it's clear after a tour of his house that he lived life to the fullest until he couldn't anymore.

Ernest Hemingway Key West writing studio

After touring the refreshingly low-key "Little White House" where Harry Truman spent a lot of time, we learn that any U.S. president can stay here, but only the ones who have visited have their name on the plaque by the gate. "That's going to kill Trump's ego if he finds out he's not listed," I remark. The next day the news reports that the angry orange one has scheduled a visit later in the week, supposedly to make a speech at a local military base. But I think he found out about that plaque...

The first night in town we have a dinner at Latitudes on Sunset Key after taking a short ferry ride over from the port. It's normally a a place you go for the views while eating outside on the water. What's on the table is fantastic, including my key lime martini, but when the sky turns black and heavy rain clouds start barreling toward us, I get an inkling of what it must feel like when you see a hurricane on the horizon. We have dessert inside and the hostess hands us an umbrella as we get ready to head down the dock for the ferry back. The winds are so powerful, however, that they snap the umbrella in two and send the top of it whipping down the beach. I look down at my hand and I'm holding the bottom of the J shape, the top of it looking like a weapon now with its sharp splinters of wood.

Key West sunset sail boat trip with wine

Thankfully the sky is clear the next night when we see Sunset Key from the water on a Wine and Sunset Sail with local operator Danger Charters. The sailboat mostly moves back and forth around the port area, but the itinerary is not the point. We go through sparkling wine, a few good white wines, and a dry rosé.. Eventually our host breaks out the red wine, but after seeing how much our boat rocks back and forth, I take a pass. Another woman on the trip lurches to the side when the wind changes direction, spilling her full cup of red wine all over her nice white pants.

North to the Lower Keys

We drive north in a rental car, seeing construction crews at work, and eventually get to the small battered marina where a bridge leads from Big Pine Key to No Name Key. We head out on a boat with Bill Keough of Big Pine Kayak Adventures to see the natural side of Florida.

Big Pine Key Florida kayaking

Bill is a naturalist and photographer who still gets excited by the wildlife around these parts. He leads us to the reef sharks and some strange algae-green jellyfish, paddling us to where the horseshoe crabs mate and the big seabirds rest between meal times. We see a loveseat washed up ashore after being blown out of who knows what house, plus a picnic table that has floated over from someone's yard. Mostly though, it's just us and the animals.

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