Why I Did a Vacation Redo

A terrible trip to Key West when I was a teenager didn’t leave me eager to return. But what I found when I went back surprised me.

Why I Did a Vacation Redo

The drive to Key West is an iconic one.

Photo by Shutterstock

The worst vacation of my life started with Thanksgiving dinner at my aunt’s house, near West Palm Beach. My mother and grandfather had a fight about my grandfather’s wife, who stayed home because she wasn’t “feeling well.” I was 15.

I didn’t feel much affection for my grandfather’s wife, so I didn’t mind her absence. My mother, though, viewed it as a slight; another way to control my grandfather, who would show up for the sake of appearances, then rush back to his wife. I tuned out the familiar arguments until my mom grabbed the car keys and drove to the mall to cool off, leaving me behind to choke down dinner with my aunt and grandfather. That night, I listened as my mom and aunt rehashed the drama. He was being manipulated. She was a jealous harpy.

The next morning, on our five-hour drive to Key West, where my mother and I were vacationing for a couple days before our flight back to Boston, I stewed. I was angry at her for leaving me the day before, angry at my grandfather for not prioritizing us, and angry at his new wife for—well, everything. I felt adrift in the family drama, but unable to actually talk about it. As we crept south, crawling in postholiday gridlock, I stared at the glittering ocean where islands were dotted, some inhabited, others undeveloped. Their remoteness beckoned. No houses. No families. No problems.

It was night when we arrived at our motel, a generic two-story building near Duval Street, and opened the door to cockroaches skittering over the floral-print bedspread. Certain we wouldn’t find anything better on a holiday weekend, we stayed put.

Key West is known for its pastel-colored homes, like this one.

Key West is known for its pastel-colored homes, like this one.

Photo by Shutterstock

The morning brought blue skies, warm weather, and better moods. We left the dimness of the motel for breakfast at a café, surrounded by blithe, muscled men in workout tanks. Their energy was a life-affirming tonic, as was the sunshine and architecture; gingerbread houses in shades of coral, yellow, purple, pink, cyan, and green, framed by swaying palms.

We hadn’t planned the trip, and even though I wanted to snorkel, we made no plans. Instead, we wandered, and went shopping. In one gallery on the Duval Strip, my mom picked out a bright-yellow serving bowl painted with a conch shell and confetti-like squiggles. I nodded in approval. Back on the street with her purchase, though, she turned weepy, the morning taking a sudden turn. She’d recently broken up with a long-term boyfriend. I rubbed her back, trying to provide comfort while secretly hoping a sinkhole would swallow us whole. Gradually, she regained her composure. Ambivalent about what to do next, we continued walking.

I pointed to one store, where rainbow windsocks fluttered on the breeze, something I hadn’t connected with the city’s LGBTQ presence. I’d hoped the store would be as vibrant inside as out, but the shelves were stocked with leather booty shorts and adult toys. I walked down the first aisle, hyper-aware of the store clerk who’d greeted us. The vibrators looked comical, displayed by color on glass shelves, but the leather gags and leashes left me with a different feeling altogether. “Yucky,” my mom said after we’d found the door and fled. I was stunned into silence, unsure of what to think.

Back in Boston, my mom and I often drove to the gay neighborhood for dinners out, where a favorite bistro was decorated with Mapplethorpe nudes, but those were tastefully suggestive, winking at gay sex without showing behaviors that were still criminalized as sodomy. I’d joined my high school’s gay-straight alliance as an ally earlier that year, and while I had crushes on guys, some of my peers suspected I was gay. Friends told me they’d heard rumors, and a few of the bolder kids asked outright.

I tried to pretend like I was above the hallway gossip, a smarter-than-my-sheltered-peers ally of the oppressed, but what if the political was personal—what if I was actually gay? Two teachers at my high school had come out after a crude, homophobic incident; aside from my mom’s hairdresser, they were the only gay people I knew. I’d avoided looking at the question of my sexuality because it seemed abstract. But the leather store, and my mother’s comment, made it clear: No matter the buoyant mood of the men on the streets, this was something to be ashamed of. Something to suppress. When I developed an intense crush on a female friend the following year, I excused it as a one-time thing and told no one. It wasn’t safe to be gay, so I wouldn’t be gay—at least, not until I got to college.

I imagined I would feel freer as an undergrad, and that turned out to be true. My fascination with women grew stronger than the fear and shame I’d felt in high school. I tiptoed out of the closet to friends and family sophomore year, got my first girlfriend, and never looked back. The leather store became a part of my coming out story; one instance among others where I’d been too scared to face the truth. And while I was grateful for those moments in hindsight, I wanted to keep them compartmentalized. They were a part of my past, not a place to visit.

One December some 20 years later, that changed.

“I have a proposition,” my mother said over the phone.

I braced myself. My mother, a lawyer with her own practice, never held back from sharing her opinion. She commented on everything from my hair to my travel plans to the plum paint color my wife and I chose for our back door, tacking on “just saying,” as if to acknowledge that I hadn’t asked for advice.

When she suggested we return to Key West, I started pacing the hallway of my home in upstate New York. Why would I want to return to the site of one of the worst vacations of my life as an adult? The cockroaches. The grief. The shame, frustration, and family tension.

It wouldn’t be like that, my mother explained. Her neighbors were escaping the New England winter with a house rental that had extra bedrooms, and they’d invited us to visit. My mom would play bridge, I could write, and we’d dine with our hosts. My wife could come, too. “Just check it out. I sent you photos,” she encouraged. Her restraint intrigued me, so I said I’d take a look.

The neighbors’ Old Town Key West vacation rental was charming, a Sears kit house lookalike with bougainvillea hedges and a tiled front porch that looked perfect for writing. The backyard pool, lounge chairs, and tropical plants suggested a private oasis. As I swiped through the photos, I let the idea float and settle. The thought of going back to a place I’d disliked so intensely felt strange, even sinister, and anathema to the very idea of vacation. We travel to feel freer, after all. Not to salt old wounds.

Yet the proposal was intriguing. I liked her neighbors. I’d never really gotten to see Key West, so beset was I by the baggage of divorced-family drama all those years ago. And I was an adult; I’d lived lifetimes since that failed vacation. In addition to writing my novel in Key West, could I write over the bad trip with a good one?

There was only one way to find out.

The concrete buoy advertising Key West's proximity to Cuba.

The concrete buoy advertising Key West’s proximity to Cuba.

Photo by Shutterstock

The neighbors’ guesthouse was within walking distance of Mallory Square, where tourists gathered to watch the sun slip into the turquoise ocean while buskers and street magicians worked the crowds. Dotted among the cottages of Old Town were juice bars and a parrot sanctuary and a men’s-only hotel. The atmosphere was quirky but discreet, as if each cottage’s manicured garden gate, dripping with red and green party beads, offered admission into its own private paradise.

Time had centered my memories of the first trip on the leather store, and the shame I’d felt, but I was curious to see what I’d missed, all the while expecting that some things might look familiar. Instead, Key West’s newness was disorienting, as if the map had been redrawn since that first visit.

I’d never seen Truman’s Little White House, clad in patriotic bunting, or the concrete buoy advertising proximity to Cuba, where selfie-seekers posed before a sprawling ocean. I couldn’t recall the roaming street chickens, reportedly turned loose after cockfighting was outlawed, or the missing-because-it’s-so-frequently-stolen Route 1 zero mile marker, denoting the start of the country’s longest north-south highway.

On Duval Street, I looked at shops offering beach cover-ups and home decor screen-printed with starfish, anchors, and shells. I wanted to find the store we’d rushed out of years ago, or the art gallery—some landmark to anchor a memory—but I couldn’t. Though rainbow flags still waved along Duval, straight tourists replaced the gay men I remembered. Only a trace of my memories remained in the revelry coming from the street’s numerous bars.

That night, friends of the hosts, a gay couple, stopped by the house for drinks. They wanted to know how my wife and I met. I grew shy in the spotlight while she launched into our story, a failed setup that eventually found footing. I’d been out and proud since age 18, and my mother was now supportive of my sexuality, but the old discomfort sometimes resurfaced. I reminded myself that I was safe, happy, and settled—all things I’d once assumed I’d never have when I was younger.

The next morning, the three of us went on a mangrove kayak and snorkel tour. Fifteen months earlier, Hurricane Irma had slammed the Keys with 150-mph winds, devastating coral reefs, but the sponge garden we visited had been spared. Lacy sea fans bobbed in the waves, while vase-shaped sponges provided shelter for juvenile fish.

We kayaked into a tangle of mangroves, pulling on the tree limbs to navigate the tight passage until it opened to a sheltered, sun-lit interior. Sand trapped in the mangrove’s roots would solidify over time, creating new islands. The tour guide’s ecology lesson suggested a continuity that was larger than our lives, and that grounded me.

Whatever I’d felt in Key West on that long-ago trip, it wasn’t here anymore. Now gardens burst with colorful blooms, mama chickens tended their fluffy broods, and crowds gathered on the pier to watch the setting sun. There were things here I liked; things that spoke to me. Like sand trapped in mangrove roots, my identity had solidified since my teen years. I was open to the process of becoming.

>> Next: Seeing the World Through Rainbow-Colored Glasses

Lindsey Danis is a queer writer based in the Hudson Valley who writes about food, travel, LGBTQ topics, and personal finance for magazines and online publications.