Florida Keys Memories

Childhood in South Florida

I lived down in South Florida as a kid, growing up there during my early elementary school years. We lived in Fort Lauderdale and Miami, and we went to the beach all the time, or at least as often as we could.

Our whole family would pack up sandwiches, hard-boiled eggs, and canned drinks. My parents would put beer in the cooler, and sometimes we would barbecue chickens on the grills. It was something we all loved, partly because it was so inexpensive. We would often get there early and stay all day.

We also took longer trips, sometimes driving down into the Florida Keys, which were probably an hour or two away. We would spend the day swimming down there, then drive back at night. That always seemed like a long drive because we would wait until dark, when the traffic slacked off, so we could swim right up until sunset.

Those warm-water trips became some of my earliest memories of travel, family adventure, and the simple pleasure of spending an entire day outdoors.

Camping in the Keys

Eventually, one year, my dad cashed in all of the Raleigh cigarette coupons that came with each pack he smoked. Back then, cigarette companies had catalogs where you could choose different items, and we chose a Coleman lantern, a Coleman stove, and a Coleman tent — all as bonuses from his smoking Raleigh cigarettes.

Now we could camp down in the Keys and stay for a night or two.

I remember staying at Bahia Honda and Long Key State Parks all the time. I have so many wonderful memories of hanging the lantern off the pier or docks at night and fishing with my younger sisters.

Mostly, I remember swimming in the warm water and loving just being down there.

We lived in Florida until I was in ninth grade, so we had a lot of good years like that. Even in eighth grade, our class trip was to the beach in Florida. But the next year, in ninth grade, we moved up to New England, where I lived for the next thirty-five years.

Even then, I would always go back down to the Florida Keys every chance I got.

Returning from New England

After we moved to New England, the Florida Keys never really left me.

It seemed like we went back to Florida almost every winter during those years, usually for a week or two, just to escape the cold. And whenever possible, the Keys were always the ultimate destination.

One funny side story from my childhood involves our neighbors when we lived in Florida. They owned a boat and would head down to the Keys almost every weekend during lobster season. They paid me to feed their dog, Noto, while they were gone.

Funny enough, I don't remember ever eating any of the lobsters they brought back. My parents probably did, but I don't remember it.

That always seemed a little strange because just a few years earlier, when I was five or six years old, we lived in New Orleans. My dad worked downtown, and on Friday afternoons he would often stop by the docks and buy fresh seafood directly from the fishing boats. He'd come home with big bags of crabs, oysters, and shrimp, and we would have huge Cajun crab boils with our neighbors.

We lived on a large circle with a common area in the middle, and those seafood feasts became neighborhood events.

I ate all kinds of seafood in New Orleans. But somehow I don't remember eating much lobster in Florida.

When I was younger and living in New England, I often imagined someday moving down to the Keys permanently. I didn't dream about becoming wealthy or owning a big house on the water.

My dream was much simpler. I imagined finding a small studio apartment, getting a job at a local boatyard, and spending my days outdoors. I'd clean boats, scrape barnacles, help launch and haul vessels, repair equipment, or do whatever work needed to be done.

I'd spend my days surrounded by salt air, sunshine, seabirds, and the sound of boats moving through the channels.

It wasn't a dream about making money. It was a dream about living simply in a place that I loved.

The Keys and Hostels

One of my favorite early adult Keys memories came probably around 1981, shortly after I got married.

We had traveled to Georgia to spend Christmas and New Year's with my wife's family. After a few days, I was bored out of my mind and desperately wanted to get down to the Keys.

She wasn't interested.

So the morning after Christmas, I took the car and headed south by myself.

I spent a week camping in the Keys and stayed a few nights at the youth hostel in Key West. The hostel was a lot more fun in those days than it is now, but it's still there. Today it's known as the Seashell Motel and Hostel, only a few blocks from Duval Street.

The hostel scene was different back then. Travelers spent more time talking, sharing meals, and creating adventures together. The Keys became one of my favorite places to meet people from around the world.

Over the years, I took at least five different girlfriends to the Keys. Between those trips and countless visits on my own, I stayed at just about every kind of lodging imaginable, especially the old mom-and-pop motels that used to define the Keys.

I also ate at dozens of classic restaurants, many of which are still around today.

Julie and the Everglades Adventure

In 2003, one of my closest travel friends, Julie, contacted me from London.

We had met the previous year at a hostel in New Hampshire and had spent months exploring New England and New York together, mostly hiking, backpacking, and wandering around the mountains. We shared a love of adventure, and over time became very good friends.

When she said she wanted to come visit, I suggested we meet in Florida and spend a week exploring the Keys.

She flew into Miami from London, and I arrived around the same time. We rented a car and headed south.

The trip followed a familiar pattern. We stayed in small mom-and-pop motels, ate at local restaurants, spent hours sitting in hammocks, explored different parts of the Keys, and generally did all the things that I had always loved about being down there.

By the end of the trip, we worked our way back north and eventually ended up staying at the Everglades Hostel, one of my favorite places in Florida.

Then came a conversation that surprised me.

While we were eating at a restaurant one evening, Julie admitted that she really hadn't enjoyed the Keys very much. Her description was memorable. She said the Keys felt like "a beach on a motorway."

I was honestly a little shocked to hear it. To me, the Keys represented freedom, sunshine, adventure, and some of my happiest memories. But from her perspective, the islands felt crowded, busy, and too dependent on the highway that connected them all together.

A few days later, she decided to fly back to London early.

I stayed.

While hanging around the hostel, I met three other travelers. Before long, the four of us had signed up for an overnight canoe trip into Everglades National Park. Along with a guide, we loaded our gear into canoes and paddled deep into the backcountry.

That night we camped on an island called Lard Can Key.

It turned into one of those spontaneous adventures that ends up becoming the highlight of an entire trip. We paddled through the mangroves, watched the sunset over the Everglades, shared stories around camp, and spent the night surrounded by one of the most remote landscapes in Florida.

Over the years, Julie and I have talked about that trip many times. Eventually she came to realize that she had probably missed out on a pretty incredible adventure by leaving early.

But travel is funny that way. Sometimes you don't appreciate a place until years later. And sometimes the best memories come from the unexpected detours that happen after your original plans fall apart.

Angelica Discovers the Keys

One of my favorite Florida Keys memories happened in 2004.

At the time, I was dating a woman named Angelica who was definitely not a beach person. Most of our adventures together involved hiking in the mountains, backpacking, winter camping, and other outdoor activities that had nothing to do with warm water or tropical beaches.

I was planning a week-long escape to Florida to get away from the New England winter and fully expected to make the trip alone.

At the last minute, Angelica decided, "What the heck, I'll go."

I'm really glad she did.

We ended up having an incredible time.

We stayed in quirky little mom-and-pop motels, ate seafood almost every day, and spent evenings sitting on the beach or relaxing in hammocks with a few beers, often talking until midnight.

Like so many visitors before her, she slowly started falling under the spell of the Keys.

On our final day, we rented a glass-bottom boat and spent much of the day snorkeling. We explored the clear water, did a little skinny dipping, and stayed out enjoying ourselves until early afternoon.

The only problem was that we had a flight out of Miami that evening.

Before we knew it, we were racing back toward the mainland, trying to get cleaned up, return the rental car, and make it to the airport in time. It turned into one of the most nerve-wracking drives I've ever made.

After all that stress, we finally arrived at the airport feeling relieved that we'd made it.

Then the airline announced that the flight had been overbooked. At first they offered travel vouchers for anyone willing to give up their seat. Then they raised the offer. And raised it again.

Eventually, the offer climbed to nearly $2,000 per person.

I thought it was the deal of a lifetime and kept trying to convince Angelica that we should take the vouchers, stay another night in Florida, and extend the vacation. Unfortunately, she had already taken about ten days off from work and absolutely had to be back the next day.

So, despite the temptation, we climbed aboard the packed flight and headed home.

Looking back, I still think about those vouchers and wonder what another day or two in the Keys might have been like. But even without the extra time, it was one of those trips that perfectly captured what I love about the Florida Keys.

Three Nights in Key West

Around 2015, I was dating Cindy, and we decided to take a trip to South Florida.

As usual, our destination was the Florida Keys.

Before heading south, we spent a few days in the Everglades, staying at the Everglades Hostel. I've written about that place elsewhere, but it deserves another mention because it was one of the most unique hostels I've ever visited. Over the years, I stayed there many times and met travelers from all over the world. Unfortunately, it was eventually devastated by one of the hurricanes and never quite recovered.

After a few days in the Everglades, we headed into the Keys.

We had a great time exploring, but eventually decided to continue all the way to Key West. At the last minute, Cindy found a small place to stay just a couple of blocks from Duval Street. It was reasonably priced, had a kitchen, and came with two bicycles that guests could use for free.

That turned out to be perfect.

We parked the car when we arrived and didn't move it again for three days.

Instead, we rode the bikes everywhere.

Every evening we'd bike into town, wander Duval Street, eat seafood, listen to music, and enjoy the nightlife. Most nights ended at places like Sloppy Joe's, the Green Parrot, or Margaritaville.

And most nights didn't end until around four o'clock in the morning.

We'd ride our bikes back to the hotel, sleep for a few hours, and by noon we'd be up and doing it all over again.

One thing we quickly learned was that Key West often gets more interesting after midnight than before it. The tourists gradually disappear, the restaurant workers get off work, and a completely different crowd comes out to play.

Some of the most entertaining people we met were members of the local gay community, many of whom seemed to start their evening around two in the morning. One night we saw an entire group wandering around town wearing little more than colorful bandanas.

It was classic Key West. Nobody seemed surprised. Nobody seemed to care. Everyone was just having fun.

Our favorite music venue was the Green Parrot.

On our final night, Donna the Buffalo was playing, one of my favorite bands. We'd already watched their early warm-up set and their main evening performance, and were standing about five feet from the stage waiting for the midnight set to begin.

Then Cindy's phone rang.

The music was too loud for her to hear, so she stepped outside. About twenty minutes later she came back looking serious.

"Bad news," she said. "We need to talk."

We walked outside.

The call had been from the police. Her daughter Brenlin, who was about sixteen at the time and home alone at our house, had apparently decided to throw a party.

Not just a small party.

A very large party.

According to the police, there were around a hundred teenagers at the house, along with plenty of underage drinking. The police had shut it down and were now calling the parents.

Including us.

At that moment, our Key West vacation effectively ended.

We skipped the midnight Donna the Buffalo set, rode back to the hotel, packed our bags, and got a few hours of sleep before getting up around four or five in the morning to begin the long drive back to Tampa.

It was not a very cheerful ride home.

When we arrived, the house looked exactly like what you would expect after a teenage party involving a hundred people. There were bags and bags of empty beer cups and vodka bottles everywhere.

And to make matters worse, my cat Tika had disappeared.

The next several days involved cleaning up the aftermath and dealing with the police. Fortunately, Cindy was eventually able to work out an arrangement that kept Brenlin from getting into serious trouble, although it involved a lot of conversations and paperwork.

At the time, it certainly didn't feel funny. But looking back now, it has become just another one of those Florida Keys stories.

A trip that started with bicycles, seafood, tropical sunsets, and live music ended with police phone calls, a frantic drive across the state, and a teenage party gone completely off the rails.

And somehow, that's exactly the kind of unpredictable adventure that seems to happen when you're traveling.

Favorite Places Today

Today Kym and I still visit the Keys at least once or twice a year.

Since we live in the Tampa Bay area, it's an easy getaway and still one of our favorite destinations.

Most often we stay in Key Largo at two wonderful old-school waterfront properties: the Pelican and Sunset Cove.

These are exactly the kinds of places I love — pastel-colored cottages and motel rooms, many of them dating back sixty or seventy years. Both sit directly on the water and have docks, hammocks, small beaches, and complimentary kayaks.

They're also within easy walking distance of several excellent restaurants, including Mrs. Mac's Kitchen, High Tide, Snook's Bayside, and even a small mead brewery right across the street.

What I especially like is that both properties have large, welcoming common areas where travelers naturally gather in the evenings. If the weather turns bad, people sit under covered pavilions and swap stories. They're the kinds of places where conversations with strangers often turn into friendships.

In fact, either property would make a perfect location for a family reunion.

And then there is the drive itself.

The drive from Key Largo all the way to Key West is one of the great road trips in America. It isn't particularly long — only about two and a half hours if traffic cooperates — but the scenery is spectacular.

The road crosses dozens of bridges suspended above water that changes color every few miles. Deep blues blend into turquoise, aquamarine, emerald green, and every shade in between.

People fish from bridges. Boats drift across the flats. Pelicans soar overhead.

Even after all these years, I never get tired of that drive.

Why the Keys Still Matter

I've now been visiting the Florida Keys for more than sixty years.

I've gone there as a child, as a teenager, as a newlywed, with girlfriends, with friends, with family, and now with Kym.

The drive to Key West remains one of my favorite drives in America.

The bridges. The turquoise water. The fishing boats. The sunsets. The tropical breezes.

But more than anything else, it's the memories.

Every bridge, every dock, every hammock seems connected to another story.

Some stories are quiet and peaceful, like fishing under a Coleman lantern with my sisters. Others are chaotic and hilarious, like racing home from Key West after a teenage party exploded back in Tampa. Others involve friendships, hostels, winter escapes, and spontaneous adventures that only happened because a plan changed at the last minute.

After all these years, I still find myself looking for excuses to head south and spend a few more days in paradise.

The Florida Keys have changed a lot since I first went there as a kid. But they still hold that same pull for me.

Warm water. Salt air. Old docks. Friendly strangers. Seafood. Music. Hammocks. Bridges. Sunsets.

And memories everywhere.