The Drive That Started It All
I was a kid from New England. Florida wasn’t a real place to me — it was something that happened on TV. Game shows were filmed there. Old people lived there. Mickey Mouse lived there. That was the full extent of my understanding of the state.
Then my parents loaded us into the car and pointed it south.
The drive from New England to Florida is one of those American road experiences that doesn’t get nearly enough credit. You watch the country change through the window like a slow-motion documentary. The bare November trees of Connecticut give way to the scrubby pines of New Jersey. Maryland goes flat. Virginia softens. By the time you hit the Carolinas, something in the air has shifted — it smells different, feels different, and if you’re a kid who grew up shoveling snow in January, it feels nothing short of miraculous.
Crossing into Florida is a genuine moment. The light changes. The palm trees appear. The temperature on the dashboard — if you’re lucky enough to have one — ticks upward in real time.
I pressed my face against the glass like a golden retriever meeting the ocean for the first time.
Walt Disney World
The reason a million New England families point their cars south every year
Walt Disney World Through the Eyes of a New England Kid
Here is what they don’t tell you about Walt Disney World when you’re a kid: the magic isn’t really the rides.
It’s the scale of the thing. You come from a small town, a small school, a small winter — and then you walk through those gates and the world suddenly expands. The castle is real. The parade is real. The heat rising off the pavement and the smell of popcorn and the sound of music coming from somewhere you can’t quite locate — all of it adds up to something your young brain can’t fully process.
We did it the right way: full days, multiple parks, characters at breakfast, sore feet by 3pm. My parents navigated it with the calm efficiency of people who had saved for this trip for two years and were going to enjoy every dollar of it.
Orlando in those days was different than it is now — less sprawl, less infrastructure, but the same fundamental promise: you drive south far enough and the rules of ordinary life temporarily suspend. The theme parks delivered on that promise completely.
What I remember most isn’t any single ride. It’s the feeling at the end of the last day, when we drove back to the motel and I realized this was almost over, that we’d have to point the car north again, back toward the cold and the gray and the school schedule. That feeling of not wanting it to end — that’s the thing that turned me into a travel person.
Florida planted that seed. Every trip I’ve taken since — solo, with a partner, with friends who’ve never been — is chasing some version of what I felt looking back at those lights in the rearview mirror.
St. Augustine
The oldest city in America — and the place that made history feel alive
The Stop That Surprised Me Most
We made a lot of stops on that trip. Florida is longer than it looks on maps — the drive from Jacksonville to Miami alone is nearly 400 miles, and it rewards people who treat the state as a destination rather than a highway.
St. Augustine was the stop that surprised me most, even as a kid too young to fully appreciate it. The oldest continuously occupied European settlement in the United States — founded in 1565, more than 55 years before the Pilgrims landed at Plymouth Rock. As a kid from New England who’d grown up believing New England invented American history, this was genuinely shocking information.
The old city is cobblestoned and dense and full of Spanish colonial architecture that looks like it belongs somewhere in Europe. Castillo de San Marcos, the massive 17th-century fort at the water’s edge, is the kind of place that makes history feel real in a way that no classroom ever does. I walked through those walls and understood, maybe for the first time, that the story of this country is older and stranger and more layered than I’d been told.
My parents were smart to build in that stop. They understood — even if I didn’t at the time — that the best trips mix the spectacular with the genuinely educational. The theme parks gave us joy. St. Augustine gave us something to think about on the long drive home.
What I’d Tell a New England Family Planning This Trip Today
The drive is still worth doing. Don’t fly if you have the time. There’s something formative about watching your own country scroll past the window for 22+ hours — it gives children a sense of scale that a two-hour flight can’t provide.
Break it up over two days in each direction. Stop in St. Augustine for at least an afternoon. Hit the beach in Clearwater or Miami if you can — one of those powdery Gulf-coast beaches or the electric blue of the Atlantic will be more memorable than half the theme park rides.
And for the theme parks: plan ahead, buy tickets in advance, get there when the gates open, and take a real break in the early afternoon when the Florida sun turns serious. The first-time magic is a finite resource. Spend it well.
The State That Never Left Me
I’ve been back to Florida more times than I can count since that first family trip. I’ve driven it end to end, explored its coastlines, sat in spring training bleachers eating sunflower seeds, visited friends and family who made the migration south that so many New Englanders eventually make.
Every time I cross that state line, I feel a version of what that kid felt pressing his face against the car window. The light is still different. The palm trees are still there. The air still smells like something about to happen.
Florida got into me young, and it never really left.
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