Classic Cars: Grown-Up Toys: Planes, Cars and Sailboats

car cloud
Photo: paisan191/iStock/Thinkstock

I’m cursed by having a passion for expensive toys. Sometimes I wish I liked less-expensive things like butterfly-collecting, or golf. But I like vintage collector cars, airplanes and rather large sailboats. The other major problem is that I don’t manage a hedge fund or have a clothing line. Joel Grey and Liza Minnelli hit it right on the head when they sang “Money Makes the World Go ’Round” in the film Cabaret.

Everything has gotten so darn expensive. It has been said when referring to sailboats “that man has never invented a more expensive way to go slow.” However, what fascinates me about these beautiful floating vessels, with their clouds of sail drifting along, is that they are seemingly powered by nothing. Unlike other contraptions of transportation, wind-powered sailboats move with no noise. When compared to a sailboat, cars and airplanes are simply obnoxious.

Sailboats are not a free ride. First, unless you own a waterfront home on deep water, you have to pay for a dock to park your 35,000 pounds of fiberglass. You will also learn to hate salt water and birds. Birds love to sit on the mast and use beautiful white fiberglass as a toilet. Saltwater seems offended by boats on its surface and bites the bottom of all boats, big and small. And it hurts, usually in your wallet. Smart owners hire divers to swim under their boats each month to pry and scrape all the slime and barnacles that magically appear, just to piss off all hapless boat owners.

Collector cars. It has been said that man has not invented a more expensive way to go fast than investing in a high-line collector car. What I mean is that usually the faster a collector car is, the more it costs. It seems Ferraris, which have always been the fastest cars on the planet, have the most value. Certain model Ferraris sell for millions of dollars. Old race cars, which at one time were worth nothing, bring the most money. Many years ago I was offered a Ferrari GTO and a 427 Ford Cobra race car. The GTO was $7,500 and the Cobra was $5,000. I thought they were both overpriced. That Ferrari is worth around $14 million today and the Cobra maybe $2 million. Who knew? Every senior car collector has similar tales. Collector cars are a good investment. Just know what you are buying. Food for thought. Purchase the best you can buy and be prepared to keep it for the long haul. It also doesn’t hurt if it’s fast and beautiful and is not a four-door sedan.

Airplanes. It has been said, mainly by pilots, that “Flying an airplane is hours of boredom interrupted my moments of sheer terror.” Sure, I’ve scared myself a few times, so has every pilot. However, single-piston-engine general aviation airplanes, as they are called, are safe little birds, and most accidents are caused by pilot error. Thankfully, there are a lot less dumb pilots up there than dumb drivers down here. Another fact—there are no better engines made in the world than the engines in those little planes. For obvious reasons, they are very dependable.

Interestingly, most new moderately priced cars are actually faster in top speed than a single-engine airplane and they are also more expensive than a good used airplane. The appeal of a plane is the freedom of flight. An airplane is like a very noisy sailboat. Air is its savior and its reason for being.

Contact Bob Gelber at

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