Schooners are a dying breed of sailboat. With two or more masts, they were the workhorses and greyhounds of their day. Today few remain, and of those, even fewer can be raced. Each year The Great Chesapeake Bay Schooner Race hosts schooners from Florida to Maine in a challenging 127 mile, overnight race down the bay from Annapolis MD to Portsmouth VA. Racing in four classes the field has included “Columbia”, Pride of Baltimore, Virginia, Woodwind and about 20 other privately owned boats. It’s a mad dash through all sorts of October weather. Join me through the calms, mishaps, waves, and general camaraderie and mayhem that make up this race.