The decentralized master planning of Seaside, Florida

This is part of Reason‘s 2025 summer travel issue. Click here to read the rest of the issue.

You might not expect there to be much for libertarians to like about a town that boasts a master plan, where design conformity is rigorously enforced across virtually every building and street, and whose admirers wax poetic about a building code that covers “everything from building materials to roof pitch.”

But Seaside, Florida, often defies expectations. It’s a town built on political contradictions: Its surfaces are planned and regulated down to the last nail, but it boasts of individual freedom in its building designs. It was founded on neo-hippie environmental and communitarian ideals, but it was privately built on explicitly capitalist notions of urban development. It’s designed to feel like both a tiny town and a big city, with the comfortable intimacy of small village life and the walkable amenities of a major metro area. It’s a haven for structural conformity, but it played an important role in bringing more choice in education to one of America’s biggest states. It’s a utopian architectural vision that resists pure utopianism.

If you know one thing about Seaside, it’s probably that it was the principal filming location for the 1998 film The Truman Show—the story of a man living a life of seemingly idyllic ordinariness in what amounts to a fantasy of American small-town life. It turns out that every aspect of his life has been contrived and constructed for other people’s entertainment: He’s the sole nonactor in a television show about his life, and his perfect little town is actually a vast set on the world’s largest soundstage, with every detail, from tiny interactions with neighbors to the timing of the sunrise, stage-managed by a godlike producer character watching over his every move. (Amusingly, the house used in the movie is the childhood beach getaway of Matt Gaetz, the controversial former congressman whom Donald Trump nominated to be attorney general.)

The Truman Show is a story of liberatory self-awakening, in which a man must escape from a planned paradise that is also a prison. But in the real world, Seaside is the sort of place people want to escape to—precisely because of the meticulous planning.

Envisioned in the 1970s by a group of young, forward-thinking architects who saw themselves as holistic community planners rather than merely building designers, Seaside was meant to embody an ideal of unhurried, beachside life, away from both the stress of the big cities and the cookie-cutter isolation of the suburbs. Over the years, it has become ground zero for a popular and influential vision of American city planning known as New Urbanism.

Building began in 1981 with what the city’s founder Robert Davis has described as a “conservative business plan and a progressive, perhaps even radical, social plan.” In the 2013 book Visions of Seaside, a collection of essays on the town’s architectural history and ideals edited by Dhiru A. Thadani, Seaside’s planners and residents write expansively about the alleged evils of suburban sprawl and necessity of “liberating” people from cars. But they also position the town’s development within the context of “the specific, distinctly, if not quite uniquely, American tradition of capitalist-sponsored town development, a tradition that existed for 100 years before World War II.”

Seaside isn’t a movie set, but even apart from its connection to The Truman Show, it can feel like one. The town employs a distinctive color scheme of weathered whites and beachy pastels, with wood slat home construction and community buildings that show off stately columns meant to evoke a nostalgic Americana. On sunny spring days, the streets are crowded with tourists, many of whom come simply for the town’s ambiance.

If you’re planning your own trip to Seaside, make sure to book several hours just for walking around. The town sits on some of Florida’s most stunning beachside real estate, with soft sand that is nearly snow white and Gulf waves that sparkle emerald green in the right light.

Beyond the natural amenities, commerce is central to the town’s vision of itself. Walk in from the beach and you’ll find a boardwalk speckled with cute, quaint shops, selling beachy clothes and ice cream. Stroll across the street and you’ll encounter the grand lawn, surrounded by shops that have become a central part of the town’s character, including Sundog Books and Modica Market, a deli and specialty grocery market that was featured in The Truman Show. And if you’re staying for a meal, be sure to stop in at Bud and Alley’s, a Seaside institution that has been in business since 1986, and which was named after two of the town’s earliest residents, a dog (Bud) and a cat (Alley).

Combined with the tidy meticulousness of the townscape, the throngs of flip-flop–wearing tourists can make Seaside feel a bit like Disneyland. It’s no surprise, then, that Seaside’s closest analog—and, perhaps, competitor—is the central Florida town of Celebration, a master-planned community founded in the 1990s by The Walt Disney Company.

The structures may be tightly controlled, but outside of the vast main lawn the landscaping is not: One of the early rules was that home builders could only clear a small buffer around the construction zone. The rest of the original foliage had to be left in place, unkempt and wild, which means that today the town’s residential streets are marked by overgrown trees and bushes, giving the roads a lush, green, pleasantly shaggy character.

Even the town’s zoning rules are derived from a more propertarian, decentralized understanding of city building codes: Seaside was an innovator in “form-based” building codes focused on aesthetics and ideals. This approach leaves individual property owners with far more flexibility to build personalized, individualized spaces, particularly when it comes to home interiors, than they have under more traditional zoning rules that focus more on strict land-use regulation.

Built on an initial plot of 80 acres that Davis’ father purchased in the 1940s, Seaside is a grand vision of intimate small-town life, organized around a vast, grassy town center that features a mix of shops and community buildings, including a tiny post office. Serendipitous community engagement is part of the design schema: Many Seaside houses feature expansive screened-in porches meant to draw people out of their homes, originally built without air conditioning, on warm evenings. The design was meant to facilitate free-range childhoods: In Visions of Seaside, longtime resident Isaac Stein writes of walking and biking to school on his own as he grew up. “I thought it was normal for kids to be free after school to explore,” he writes. “I felt more like an adult. I was able to mature at a young age, function on my own.”

The city’s approach to education also has more room than most places for innovation and local control. In the 1990s, a group of Seaside parents wanted to create a small, local school. The result was the Seaside Neighborhood School, which was built with funds raised from the filming of The Truman Show and went on to become one of Florida’s earliest and most successful experiments with charter schooling. It helped kick-start Florida’s education reform movement, and is now the oldest active charter school in the state.

The master-planned aesthetic order of Seaside won’t be for everyone, and the control it exerts over its streets and houses will irk those freedom lovers who prefer a more anarchic urban disjunction. But the pleasures of Seaside—and even its critics tend to admit that it is exceptionally, perhaps even eerily, pleasant—have arisen primarily from private entrepreneurship and local efforts, from contractual controls and decentralized development, from the way it has balanced communal norms with private preferences. The most unexpected thing about Seaside is that it somehow channels all of these impulses simultaneously, pulling together disparate worldviews and ideologies into a coherent whole. It’s restrictive. It’s liberating. It’s both—and that’s what makes it so special.