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key west revisited
memories of margaritaville
by dirk cotton
pop culture

A long time ago, in a galaxy far, far away, and before my wife and I had kids, we made a few trips to Key West in February, when the winters in Washington had begun to take their toll. In the mid-80’s, you could stroll the relatively quiet Duval Street and hear Jimmy Buffet wannabes playing in nearly every bar in town, even in the middle of the afternoon.

I would listen to Buffet for a week before every trip just to get in the spirit of things and for a few weeks after because I couldn’t stop.

The people who grew up there called themselves Conchs and begrudgingly offered the label “freshwater Conchs” to recent arrivals who had lived there a mere twenty years or so. The rest of us were just tourists.

They lived in small, wooden houses, creatively called “Conch houses”, right up to the edge of the downtown area. According to a guidebook, Key West still has more wooden structures than any other town its size in the country. Conch houses were a staple of tours on— you guessed it— the Conch train.

The high point of every day was and is the sunset celebration at the Mallory Square docks. People would show up about an hour before sunset, perhaps buy a drink at the only large hotel in town, the Pier House, and watch and listen to street performers until the magic moment. The crowds would number 150 on a good night.

The sun’s disappearance generated a round of cheers and served as the official starter’s pistol for an evening of dinner and barhopping.

We always stayed at a small bed-and-breakfast on Fulton Street called Eden House. It had a dozen or so rooms with shared baths, a huge upstairs front porch and no air-conditioning. In February, the screened windows kept the rooms at a delightful temperature day and night, Key West being just 25° above the equator. It was hard to imagine being there in summer, though.

The Eden House had a wooden walkway around the second floor just outside our bedroom windows. One night a sound awakened me about 2:00 a.m. and I stared out the window to see a lovely young lady standing by the railing and enjoying the view. I couldn’t help but notice that she was completely naked. I doubt she enjoyed the view as much as I did.

Eden House had a lovely swimming pool and served breakfast on the veranda next to it. Their specialty was cinnamon coffee. Flavored coffee was uncommon then and it seemed like such a treat.

Key West had a tiny airport, more of an airstrip, but we flew down once after connecting in Miami to avoid the four-hour drive. We flew on a DC-3, the planes whose tails sat nearly on the runway before takeoff so that you walked up a steep incline to your seat and sat facing upwards. As the plane picked up speed down the runway, the tail would lift and you would sit level until you landed.

Providence-Boston Airways provided the service. They flew the DC-3 from Boston to Martha’s Vineyard in the summer and moved it to Key West in the winter. We were told it was the last DC-3 in commercial service. We had an amazing, low-altitude view of the Everglades as we flew down.

A year or so later, a few of PBA’s planes actually flew into the Everglades instead of over them (you can overdo the low-altitude thing) and the airline went out of business. So much for nostalgia.

We loved Key West because it was tropical, low-key and had this amazing Margaritaville vibe. Knowing that you weren’t a Conch and would always be an outsider wasn’t a negative; it gave you the feeling that you were visiting someplace exotic and exclusive.

After we had children, we looked for more family-friendly resorts with real beaches and ended up in Sanibel and Captiva, which we also came to love. Last week, with all three of our kids away at college, we revisited Key West after a 25-year absence. It has changed. Not all for the better, but not all for the worse.

Our first thought was to return to Eden House. It’s still there. In fact, it has grown and prospered, but the prices seemed high for a place so far from the action at Mallory Square. We decided to stay at the Westin by the docks, a place we couldn’t have afforded the first time around.

The two biggest changes to us were the disappearance of Conchs and the appearance of cruise ships.

Many, perhaps most, of the Conch houses anywhere close to town have been converted to restaurants and hotels. We’ve kept a print of Southernmost House when it was a private residence, sketched and signed by artist Robert Kennedy in 1980, hanging on our walls for 25 years. Southernmost House is now a hotel, albeit a lovely one.

Other Conch houses are now restaurants, B&B’s, bars, a microbrewery and, yes, a Hard Rock Café.

Where have the Conchs gone? They can’t afford to live there anymore, of course, though we hope some made a fortune selling their real estate. You can buy a condo at the Truman Annex for a million three. A local barista told us the consensus is that within twenty years no one will actually live in Key West. It will be a commercial area manned by employees who live further up the Keys.

I fear that the cruise ships, the other big change, were a huge mistake. Cruise ships had long called on Key West, docking at the nearby Navy facilities, but in 1984 the City Commission made improvements to the city-owned Mallory Dock, making it a full cruise ship docking facility.

During our early Key West visits, we looked out at the Gulf of Mexico and the smaller keys and mangrove islands from many places around the city. Nowadays, two cruise ships a day, each larger and taller than the biggest hotels in Key West, cruise into Mallory Docks and block the view like that star cruiser in the beginning of the first Star Wars movie. City ordinances ensure that they leave two hours before sunset, but sitting in the shadow of one of these behemoths and hoping they move in time to actually see the sunset is a strange experience.

At first I worried that the restaurants and shops would be jam packed when the ships were docked, but unfortunately for Key West shops and restaurants, they weren’t. We spoke with one passenger who told us he would look around town a bit and return to the ship for lunch. The food is good and free, he explained, so why spend money in a restaurant?

The biggest revenue producers in Key West are the bars, nightclubs, restaurants and hotels. If cruise ship passengers eat lunch on the boat and have to be gone two hours before sunset, it isn’t clear what business is left for the town to justify destroying the view all day long.

Oh, there was a third change I noticed. I didn’t hear a single Jimmy Buffet song while we were there. The wannabes have been replaced by country singers, usually with a comedy shtick.

Buffet’s musical history has long been tied to Key West, a town that inspired lovely ballads and conjured up vivid images of the tropics, and it now seems to be tied to the resort’s new persona. The music Buffet puts out of late sounds more like cheap T-shirt shops than local art galleries and feels more like the town’s hundred or so Key Lime pie shops than a beer at Captain Tony’s.

The hotels are nicer, the restaurants are better and the facelift of the docks area is a welcome sight. I find Hemingway’s House and Truman’s Little White House as inspiring as ever. Still, I believe this may have been our last Key West visit.

The year after that lovely apparition appeared at the balcony rail in the middle of the night, we sat next to the Eden House pool after breakfast. A beautiful young lady was swimming alone, but she soon disappeared. As we walked up the steps to our second floor room, we noticed her drying in the sun on a chaise in the nude. Vicki chuckled as we passed by and said, “The legend lives on.”

I fear the Key West legend is dying. I like it now, but I want to remember it as it was.


Dirk Cotton is a retired executive of a Fortune 500 Internet company who loves to spend time with his family, fly fish, shoot sporting clays, attend college baseball games, sail, follow the Wildcats, and write. Everything else he does is just for fun. A computer programmer-cum-marketing executive-cum-financial planner who now wants to be a writer, he apparently can't decide what he wants to be when he grows up. He and his family moved to The Southern Part of Heaven in 2005 and couldn't be happier with that decision.

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