Yachting on a shoestring

(Fortune Magazine) -- "Owning a sailboat is like sitting in a shower, ripping up hundred-dollar bills," jokes attorney and boat enthusiast Peter Bicks.

He should know: By day Bicks is a managing partner of global law firm Orrick Herrington & Sutcliffe, heading its New York City office, but in his leisure time he is a world-class wind junkie who has been sailing since age 4. He and his family have owned a dozen boats in his 49 years (including Firebrand, a 43-foot mahogany Classic that won the Admiral's Cup and had a fireplace below deck).

According to Bicks and other experts, for those interested in testing the waters, now is actually an excellent time to buy, given the number of gently used (and massively discounted) models on the market. Short sales are happening too -- banks and brokers whose inventories are too high are now willing to let a new boat go for a loss just to get it off their books. But taking the plunge can be intimidating. We tapped Bicks for his best advice for new buyers.

Buy secondhand. These days no offer is too low: Most pre-owned boats in good condition are going for as much as 50% below the sticker price. Sailing clubs are a good source for reputable local brokers (see box at right); Bicks advises making low-ball offers to several sellers to score the best price.

Start small. Learning is much easier on a smaller boat like a Laser ($5,300) -- you'll discover how every adjustment of sail, trim, and helm changes the way the boat moves.

Keep it simple. Skip fancy navigational equipment, electric winches, extra sails, etc. A beginner needs to "get his head out of the boat" and focus on tides, wind, weather -- and other boats.

Choose fiberglass. The time and costs of maintaining a wooden boat are astronomical, and a crash will cost big bucks to repair.

Charter, borrow, or beg. Hop on as many "free rides" as possible so that you can get a feel for what you like. Sailors love to take stray deckhands along and tell them how much they know. After a day on the water, the bar is a great place for free advice and more invitations to sail.