In 1977 I took swimming lessons in the Pier House pool. I was two years old, and by the time I turned three I no longer “needed” my inflatable water wings, and my dad was proud that I could make it across the pool on my own. But I still chose to wear my water wings for comfort and assurance, and, rather than swim, I floated and clung to the tiled coping at the pool’s edge, crab clawing hand-over-hand around the pool’s perimeter, seeking shady spots from which to perch in the cool water and observe the eclectic characters lounging at the Pier House pool.

Now that I could swim, my dad felt comfortable leaving me with random bikini clad women “for a few minutes,” while he stepped into the Chart Room bar just twenty yards away to grab a drink. Dad was smooth and persuasive, and ultimately a woman would slide into the pool and cradle me against her slick, mineral spirited body, as my dad would bend down and assure me, “hey, buddy boy . . . I’ll be right back.”

The mystery women were entertaining enough. Sometimes they towed me around the pool, or I’d ride on their backs for a couple of dolphin laps. They clearly didn’t have kids and thought I was cute, and it was all fun and games for the first fifteen minutes, but then I’d start to ask, “where’s my dad?” and the tears would start to well-up, and eventually they would have enough of it and start to ask themselves, “where the fuck is this kid’s dad?”

THE CHART ROOM

The Chart Room was ice cold and dark and smelled sweet from stale beer and spilled liquor. When I heaved the door open and stepped inside wearing my water wings and wet bathing suit, it felt as though I stepped through a portal into an alternate timeline. Gone was the outside bright white heat of tropical summer, no one was wearing a bathing suit, and no one seemed particularly happy to see me. My dripping bathing suit was creating a puddle on the bar room floor, and I started to shiver, standing in the 64 degree vampire cave.

“Where’s my dad?” I asked, scanning the small, dark, low-ceiling cinderblock room.

“Who’s your dad?” the displeased bartender barked.

A bearded man with a big smile sitting at a table called out, “That’s Sunshine and BJ’s kid, Spud,” and he tried to assure me. “Your dad said he’d be right back. He had to run back to the house for a minute.”

Seeing the look on my face and the welling tears, the bartender was quick to distract, “Hey Spud. I remember you, buddy. Want a Coke?” I had never been offered a coke. I wasn’t allowed to have a coke. I was only three. I shook my head in affirmation.

The bartender said that wet bathing suits were not allowed in the bar, but he would make an exception this one time. He placed a dry bar rag on top of the first captain’s stool, hoisted me up to the bar, and gave me a cold can of coke and a bowl of Goldfish crackers to munch on. The coke was amazing! The Goldfish crackers were the perfect snack.

I was happy, and forgot about my dad, and the bartender seemed amused at his ability to manage the awkward situation. “So what’s the deal with the water wings?” he asked. “Those are for babies. You gotta get rid of the fucking water wings.”

THE PIER HOUSE MOTEL

The brilliant, gay entrepreneur, David Wolkowsky, constructed the Pier House Motel in the late 1960’s, and quickly set about metamorphosing the drab cinderblock centered property into a hip and happening scene with lush tropical landscaping, ideally located at the foot of Duval St., with a western view of the harbor. The dark, air-conditioned bar, a brand new beautifully deep and cool swimming pool, and a small harborfront beach were the primary attractions, but Wolkowsky himself was so clever and frugal and creative, and even debonair, as he managed a melange of quirky staff and zany locals that he liked to see lounging about his pool and beach, or imbibing in the shaded cool of the Chart Room Bar. It was almost Warholic, like the Factory of 1970’s Key West, with writers, artists, scammers, smugglers, musicians, gays, hippies, and freaks all welcome. Just behave yourself. And mostly they did.

Of course there were shenanigans and general horseplay, such as the Tequila Regatta, a foot and sailing race that started and finished in the Chart Room, a race course that included a swim in the pool, a run to the beach, a swim in the ocean, a sailing lap across Key West harbor, and eight shots of tequila along the way.

But, mostly it was muy tranquilo, a come-as-you-are, don’t ask too many questions, live-and-let-live locals scene with occasional tourist interactions.

THE GENTLEMEN PIRATES

From 1976 to 1981, we lived 2 blocks from the Chart Room in a grand Victorian house at 425 Caroline, across the street from the Bull & Whistle bar. Dad bought the house with a suitcase full of cash after learning how to sail on a hobie cat hauled out on the Pier House beach. 

My dad arrived in Key West in 1970, and quickly gravitated to the cast of characters that frequented the chart room. He was a good looking, smooth talking twenty-two-year-old from South Carolina, and he easily convinced Wolkowski to allow him to rent hobie cats off the Pier House beach, with the property receiving a portion of each rental. Within a year, Dad acquired a blue water vessel and organized a sailing expedition to Jamaica, returning with a boat full of ganja. After a few runs, he bought a mansion with a cash-stuffed duffle bag. It was a stimulating and addictive occupation with many hazards.

Dad was not the only hustler hanging at the Chart Room. It seemed like most of his friends were also scammers and smugglers, but interestingly, for the most part, they did not coordinate and work with each other, and they didn’t really talk about it. They just communed in that cold air-conditioned bar, celebrating their achievements.

The Chart Room was also a place to buy and sell small quantities of drugs, and was the watering hole for several local politicians, judges, and the sheriff. You have to remember, this was a frontier town in a free-wheeling era before the war on drugs. If you weren’t stealing anything or hurting anyone, you were mostly left alone. It was a live and let live community.

Jimmy Buffett eventually arrived in this scene, as did wild child Jane Slagsvol (Jimmy’s future wife). Jane was also from South Carolina and came down to visit my mom and dad and their running mate Larry “Groovy” Gray. When Jane and Jimmy collided, the sparks began to fly, and the chart room cranked-up. Jimmy brought his guitar and high energy into that very small concrete bar room, along with his journalistic eye for characters and stories. 

The Chart Room was a nexus for so many characters on the edge of the Caribbean frontier, living lives outside of mainstream American social norms, riding that liminal line between the old and new worlds, between the freedom of rugged individualism and the comfort, constraints, and expectations of an emerging modern American society. To the astonishment of many, some of these gentlemen pirates were even raising kids along the way.

THE GONZO KIDS

The Pier House was not a kid friendly property, but management and guests tolerated a few of us in moderation. Cory’s dad, Chris Robinson was a bartender at the Chart Room, and Jed’s dad, Phil Tenney, had been a regular patron of the bar since his first day on the island, when he arrived to film a fishing TV show in 1972, and the crew stayed at the Pier House, and Phil never left.

So, Cory, Jed and I were the regular toddlers in the pool and on the beach, while our dad’s held down the Chart Room. Once we ditched our water wings, the three of us shifted our focus to the beach and the crystal clear water of Key West harbor. With at least one mother watching from a distant beach chair, we would build sand castles and wade and swim in the warm shallow water, exploring the small caverns and tidal pools formed by the massive coral boulders that protected the north side of the property from the powerful harbor currents. We had learned from our swim lessons in the pool to always swim with our eyes open so we didn’t run into anything. But keeping your eyes open in salt water can be challenging, so this became one of the first contests between the three of us. We would count to three and drop under water with eyes open, looking at each other to see who could hold their breath and eyes open the longest in the salt water. Often, we would move on to skipping rocks, which quickly elevated to throwing rocks at each other, typically ending with a Pier House staffer complaining to the mom in charge.

THE FLOATING DOCK

As four-year-olds, swimming out to the floating dock was the forbidden fruit and our ultimate goal. The dock itself was a simple ten by ten wood framed floating structure moored to the seafloor by heavy chain. There was usually a topless lady or a couple of guys in speedos tanning, but there were never any kids on the dock.

Sitting in the clear shallows, digging our toes into the white sand, Cory claimed to have already swam to the dock once. Now he dared me to swim out there. I waded out till I was neck deep, then dove underwater, eyes wide open, and swam along the sandy bottom a few meters toward the dock. But the distance to the dock was more than three times the length of the swimming pool, and the bottom depth sloped infinitesimally into the deep abyss of the harbor. It was scary.

When we opened our eyes underwater looking to make the attempt, the foreboding depth of Key West harbor beneath the dock dissuaded our efforts almost instantly. We would choke in fear of the vast dark unknown below and beyond the dock. That was the harbor, where the wrong tide would easily defeat the strongest of men, and we knew there were barracudas, moray eels, and sharks.

The men from the Chart Room would egg us on, and with each attempt and more time swimming in the ocean, we became increasingly comfortable and confident and began recognizing and identifying sea creatures not as threats, but as curiosities. We started to play with masks and began noticing how many small, juvenile barracuda were swimming next to us every day. We found eels living in the rocks, and realized they never left the rocks. They were always hiding.

Our big breakthrough arrived one afternoon as we watched two stumbling drunk guys peel off their clothes and start swimming toward the dock. One of the guys held a closed fist clutching a baggie and a lighter above his head as he swam out to the dock. Cory and I looked at each other. That guy just swam out to the dock with one hand, and kept his head above the water the whole time. If he can do it with one hand, we can definitely do it. 

We decided the best approach would be to doggy paddle our way out there, keeping our heads above the water, and no matter what, do not look down into the abyss below the dock. 

With shallow breaths Cory and I doggy paddled through a couple of oncoming boat wakes, reached the dock, and climbed up the wooden ladder. We couldn’t believe we made it! Nothing ate us, and we weren’t swept into the harbor. We initiated a spastic celebratory dance and unknowingly spritzed the drunk guys trying to roll their joint, as well as a sunbathing woman who, until the drunks climbed aboard, had solace in her peaceful private tanning. She rolled over and sternly informed, “Children are not allowed on this dock!” to which we erupted in defiant screams “AAAAAHHHHHH!!!!!” and dove back into the sea, skimming the sandy bottom as we made our way back to the beach.

From that day forward, we swam out to the dock every time we went down to the Pier House beach. We even replicated the Tequila Regatta. We called it the Coke Regatta; we ordered a can of Coke from the Chart Room, ran and jumped in the pool, ran down to the beach, and then swam out to the floating dock holding our Cokes above our heads, finally climbing up the wooden ladder onto the floating dock, cracking and chugging our cold Cokes, then belching and screaming “Domingo!” into the hot sun in the middle of Key West Harbor. Our parents would tell us, “Please don’t do that if you see the manager walking around.”

THE PARTY SUITE

The First Offshore Powerboat World Championship was held in Key West Harbor in 1981, and the Chart Room crew decided to move the party into a second floor Pier House suite overlooking the harbor and the race course. Dignitaries arrived from across the country: coke dealers, musicians, boat captains, dancing girls. Hunter Thompson participated as an official sports journalist and summoned his friend Bill Murray to join the party.

Kids were not invited into the second floor suite. We loitered between the pool and the beach during race days, but management was clear: no one was allowed on the floating dock during the races, so we watched the tournament atop the sharp coral boulders on the water’s edge. Between races we ran back to the pool and played in the parking lot and out on the sidewalk on Duval Street. On the third racing day, the Chart Room 86’d us from Cokes and Goldfish crackers, so we had to use the vending machine in the stairwell, and the moms limited us to one Coke per kid per day, which we vanquished by 11am.

As the afternoon wore on, bored and thirsty, our fortune finally shifted when Jed found a quarter at the bottom of the pool. We headed to the Coke machine, but still  needed another quarter to make the 50 cent purchase. I checked the change slot, and Cory tried reaching his arm up inside the dispenser but couldn’t pull a can out of the machine. Two chatty ladies in bikinis walked past us, one saying to the other, “Let’s just go upstairs and tell them we want some more coke.” Domingo!

I think it was Cory that led the charge. Jed reminded us that his dad said we were not allowed to go up to the party, but Cory marched on and declared, “We want more coke!” and then I chimed in, and we started to chant as we marched up the loft stairway into the party suite: “We want more coke! We want more coke! We want more coke!”

We were coming in hot right into the back ends of the bikinied ladies when they reached the top of the stairs and entered the party. Bill Murray was the greeter, “Well hello, ladies . . .”  Bill smiled with locked jaw. We scurried around the ladies and into the open loft suite, which was nothing more than two queen beds, a couch and table, and a dozen coked-up pirates drinking rum, persistent and determined in their conversations. We knew all of them except for Bill Murray, who looked down at us and mused “Who are these guys?” 

Hunter raised an eyebrow and looked puzzled. There was Joe DeLuca on the couch, but he was geeked up and couldn’t quite respond verbally. Jimmy was there sitting on the edge of the bed in deep conversation with one of the scammer captains. Finally, Jim Mayer, in a low gravelly voice, answered Bill’s question, “those are the boys. Hey boys, you guys want some coke?”

“Yes!!!” Cory and I screamed.

“Here ya go,” Jim Mayer handed us a roll of quarters from his payphone stash.

“That should keep you covered for a while,” Jim grinned and took a drag from his Marlborough. We thanked him, and ran back down the stairs toward the Coke machine, where Cory’s mom, Sonia, caught us.

“I told you boys you’re not allowed to go upstairs to that party.”

END OF AN ERA

Wolkowsky sold the Pier House and made a small fortune. The scene had already begun to migrate to other local watering holes. Phil Tenney purchased Louie’s Backyard. Sidney Snelgrove and Vic Latham launched the Full Moon Saloon, and Sidney and Jim Mayer purchased Sloppy Joe’s. Jimmy and Jane moved to Aspen. Chris Robinson moved over to bartending at the Bagatelle and Louie’s. Many of the gentleman pirates migrated further into the Caribbean and Central America. 

Dad sold our house on Caroline Street, which was eventually purchased by the actress Kelly McGillis, and later by the country star Kenny Chesney. We stayed in Old Town, moving to 900 Eisenhower Drive, the only property in Key West that encompassed an entire city block. Dad doubled down on the tropical landscaping and built the largest private swimming pool on the island. Eisenhower became a legendary Key West party house and notorious homebase for the Gonzo Kids’ free-range childhood, a magical environment of adolescent adventure.

This Article Appears in Issue 6 of OurKeyWest Magazine