This book records the history of the racing yacht Chessie, the first ever entry from the Chesapeake Bay in the famous Whitbread Round the World Race. Skippered by Baltimore businessman George Collins and named after the Chesapeake's equivalent to the Loch Ness monster, Chessie became a focal point of regional and national pride when she competed in 1997-98. That year was also the first time that Baltimore and Annapolis were included as a combined stopover in the nine-leg, 31,600-mile race, beginning and ending in Southampton, England. After a neck-and-neck race up the bay against famed skipper Dennis Connor, Chessie entered Baltimore's Inner Harbor greeted by the cheers of thousands of fans. During the stopover, over a half-million visitors came to the Whitbread Race Village in Baltimore and an additional sixty thousand toured the Race Village in Annapolis, giving Baltimore-Annapolis the highest attendance of any of the nine ports visited by the race. While racing, the boat also served an educational purpose through a two-part curriculum developed by the Living Classrooms Foundation, a Baltimore nonprofit educational organization for at-risk children. Children from five hundred schools in twenty states and seven foreign countries participated through the Whitbread Education Project, a curriculum package augmented by an Internet component, the Chessie Chase, which explored academic subjects such as math, science, social studies, geography, and literature and tackled such practical issues as vessel design, ocean currents, changing weather, and the principles of navigation. Classes competed in a virtual race against each other in the multifaceted program for a chance to visit Chessie and meet her crew when she reached Baltimore. The children also exchanged e-mails with Chessie's crew throughout the race. When President Clinton and Vice President Gore visited the Living Classrooms Foundation in Baltimore, students helped them write an e-mail to the boat saying, "Have a great race." This book contains chapters on the race, boat construction, crew selection, and the Living Classrooms Foundation Whitbread Education Project. Personal experiences and memories of the crew bring the sailing adventure to life and reveal the educational purpose of the boat. Sidebars feature useful charts and information, special observations, and a few human-interest e-mail exchanges between individuals and the crew. A large Mercator-projection map marks the race course and individual legs. Numerous photos document racing action as well as the hoopla on shore.