In a way, the Icon feels like the iPod of personal planes: It's small, stylish and surprisingly intuitive. The instrument cluster I mentioned before is comprised of eight easy-to-read dials (plus a digital attitude indicator), set in an aggressive-looking plastic chassis that just screams "sports car." The shiny Icon badge stuck in the dash in front of the passenger seat keeps that visual metaphor alive. Toss in a tablet for navigation and the skies are yours. The seats are comfortable, if a little low. Cargo room? You're not exactly flush with it, but there's room behind directly behind the seats for an overnight bag and some sundries. And it's a looker too, with two folding wings lock in place over a sleek, white-and-silver cabin and a dagger-like tail jutting out from below the seats.

Aesthetics aren't everything, but Icon co-founder and CEO Kirk Hawkins can't afford to underestimate their importance. A former Air Force and commercial pilot, Hawkins talks about the deeper connections the A5 can inspire with the easy-going, polished poise of the modern startup hype man.

"Making truly great consumer products like this, that have the ability to stir you emotionally, requires a whole different order of magnitude of effort," he told me. You'd be forgiven for thinking he just created another pointless new wearable, but he's serious when he says his team "distilled flying down to its purest form." Those are some lofty claims, but Hawkins isn't shy about the time it took to get there. The Icon has been in the works for a decade, and it took a shift in FAA rules to even get the idea off the ground. In 2005 the FAA officially approved the light sport aircraft category and a relatively relaxed set of training requirements for the would-be pilots who wanted to fly them. Now, as a result, we have planes like the Icon that are in some ways meant for everyone.

"The problem with flying is the FAA really over-regulated it 50 years ago. They considered aviation difficult, dangerous, not for the public. Isolated. Then they re-thought all that," Hawkins said.

Well, fine, not everyone. Those iPod parallels run deeper than style considerations; the Icon isn't nearly as cheap as some of the other beginner's options out there. Amateur pilots often earn their first set of wings behind the stick of a single-engine Cessna or Piper, and well-worn classics like a Cessna 152 built thirty years ago can go for between $20,000 and $50,000 on the open market. Almost reasonable. More modern options like the Evektor Harmony, another handsome light sport craft, will probably set you back around $150,000 in good nick. Then there's the Icon with all its bells and whistles, sitting at the top of the beginner's heap, at $189,000. For now, anyway. Hawkins says the team is committed to quicker updates than other plane makers, so it's possible future models could cost less as the company figures out more effective means of production.

The FAA's about-face also means Icon isn't alone in its mission to democratize the skies. We're actually in something of a renaissance for scrappy aviation startups. Massachusetts-based Terrafugia has spent the last decade working on the Transition, a personal plane that will double as a completely road-worthy rear wheel drive car. It's still years away from completion, though, and the pleasure of eventually taking off from the turnpike should set you back between $300,000 and $400,000 when the Transition is finally ready. Meanwhile, companies like Cobalt have set their sights on customers with even more positive cash flow. The $699,000 Valkyrie-X is an experimental two-seater, but hand-stitched leather trim and some gloriously swoopy bodywork make it equal parts aircraft and art installation.

My own wallet weeps at the thought. Cost aside, though, the Icon is a damned fun plane. The thing about sitting in a compact plane is there's hardly any material shielding you from the sky; that's how it feels anyway. We have got the windows open and every time the pilot takes a tight turn or dips to skim the Hudson, I feel echoes of the maneuver in my gut. And when the pilot suggests we stall the plane on purpose to see how the Icon refuses to fall out of the air, I'm suddenly no longer a passenger -- I'm dead weight. My eyes, like the windscreens, are pointed up and full of blue sky. The Icon hung lazily for a few moments and recovered easily, but it took me a little longer to get over it. (Thankfully, we never needed the parachute meant to protect the plane when in free-fall.)

A few minutes later, the pilot levels off and asks if I want to take the stick. Forcing back all those childhood X-Wing dogfight fantasies, I grunt a response and keep things level for a bit. After gathering some courage, I gently shift the yoke to the left. Then back to the right. It ain't flashy, but I'm really flying a plane. Suddenly, those fantasies don't seem so silly after all. Now I just need to ask my bosses for a raise.