One of the cruises offered by Williamsburg Charter Sails is for potential boat buyers. Sailboats are in an unusual market whereby the broker or dealer is neither inclined nor obligated to take you for a test drive. To do so, you must first sign a contract to actually buy the boat and put a down payment on it, anywhere from 1% to 10%. That’s a burden that few joyriders will take, which is fine with the dealers. As a result, many boats trade hands between individuals instead, and the seller is usually willing to take the prospect out without elaborate prepayment. The larger issue is whether one should buy a boat in the first place. I discourage this behavior because a boat is a comparatively big investment that will not pay off unless you’re eager to go boating at least once a month, preferably once a week. The season can run year-round in Florida or California, seven months in the mid-Atlantic, and two months in Minnesota and Canada. Ownership entails maintenance, and that involves engine systems, water systems, lubrication systems, and more. People who like to tinker are more sanguine about maintenance than those who prefer yard work or reading. If by now the reader is still inclined to purchase a boat, I would advise renting first for a few months or an entire year. When I tell this to fellows while we’re out sailing, they start to frown because they have their heart set on a particular model. I offer an analogy: “Think of it as dating. It’s better to date a boat than to marry it.” That brightens them up. New websites such as rentmyboat.com and boatbound.com offer all kinds of motorboats and sailboats within easy driving distance. The object is to test drive as many different kinds and sizes of boats over a season to see which one appeals the most to you and the family.

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