For a starter boat, you might consider a 2012 Chaparral Ski & Fish that's 19 feet and costs about $24,000. If that's too small, a new 37-foot SeaRay 370 Sundancer would run about $400,000 at Marine Max in Norwalk, Connecticut. Prefer the sound of luffing sails to an engine's whine? While a basic 21-foot Sailfish can cost about $42,000, the latest 42-foot Sabre sailboat runs a cool $402,000. Jim Munro at New Wave Yachts in Massachusetts says extras such as electronics and a generator will jack the price up by $150,000.