Shirley Jetter fell in love with sailing during a sunset cruise in Jamaica 34 years ago. "And since then, I've done everything possible on a boat, from repairing engines to mending sails," she says.

A special-education consultant at a public school (divorced, no kids), Jetter uses summers to pursue her pastime. "But lately, work has become a distraction from my dream," she says.

That dream: to sail around the world for the next decade. Jetter's retirement "is locked in and I can pull anchor at any time." There is one consideration - buying her 56-foot dream boat, which she expects will cost $150,000.

THE REALITY

Boats don't come cheap, and the bigger they are, the more they cost. A brand-new 56-footer goes for $500,000 and up, says John Kretschmer, a Florida-based author of five sailing books who runs workshops on boat buying.

Add to that an annual upkeep of roughly 10 percent of the purchase price. That outlay would dip into Jetter's savings big-time and could exhaust her money well before she's ready to furl her sails for good, says Ryan Vander Zwart, a Holland, Mich., financial planner.