Every year my family drove from Canada to Florida to see my grandparents. I still cherish those memories.

12.01.2025 - 00:39 / insider.com

For most 8-year-olds, waking up at four in the morning would be an unwelcome experience. But for me, waking up on a frigid March morning in 1998, I was ready to go. It was our first family road trip , and we were headed down to my grandparents' Condo in Marco Island, Florida. And, in what was probably a bid to keep me quiet, my parents had bought me a brand new Gameboy with Pokémon — I was raring to go.

I didn't know it yet, but this was the first step in what would become one of the most significant annual events of my entire life .

Each year, March Break became defined by heading from our home in Ottawa, Canada , down to "The Condo" (it achieved proper noun status in my family long ago) — the year-round balmy Florida weather a welcome and almost magical contrast to the iced-over roads and gray skies of Ottawa in March.

My grandparents bought the condo after they retired in the early 90s, and my childhood winters became punctuated by two weeks of glorious heat each year.

Our first day often ended in Roanoke, Virginia, an infamous place in our family lore. This was mostly because we were all motion sick from our first day spent in a car, inevitably throwing up on our only night in town. Day two usually ended in Orlando or Tampa Bay, staying over so we kids could exhaust ourselves at Disney World , Universal Studios, or, eventually, the Kennedy Space Center.

Over the years, the story remained the same, even if the details changed: early start, sick in Virginia, hours lost on a Gameboy , and spending a couple of days at theme parks before heading to the Condo.

For me, Marco Island was a place that felt as personal as someone else's secret family recipe. It was a place only for us: nobody outside our family had ever even heard of it. A small retirement community on the shores of the Gulf of Mexico, today there are still fewer than 20,000 residents.

In the years since our first trip, Marco Island has been at the center of dozens of core memories: few were more iconic than splashing around in the pool as thickly-accented Bostonian snowbirds scowled their way through calisthenics sessions at us. Inevitably, we were the only kids in the complex aside from a couple of others who were visiting their grandparents too — we'd quickly make and forget our new friends each year, united in our days' long-shared experience of being under five feet tall.

Countless embarrassing photos have been taken (and hopefully lost), including my spot-on imitation of a pelican loitering around our favorite restaurant, the aptly-named Pelican Bend. The first time I was ever allowed to stay up until midnight was at the Condo on Y2K, watching the Nickelodeoncoverage of the big event. Teaching my younger sister how to