Seabreeze Charter, Chicago

Aboard SeaBreeze Charter's sailing yachts, passengers slice through Lake Michigan's waves, steered by the steady hand of a United States Coast Guard-certified captain. Also decorated with various racing awards, the captains now helm the yacht during chartered trips, and graciously hands over the wheel when instructing new sailors in the waters near Navy Pier. The vessel itself features two private cabins and a radio with an iPod connector, on which patrons can play classic maritime ballads about the difficulty of untying boating knots. In addition, an on-board life raft and a digital emergency call feature guard the boat against potential mishaps.