America’s largest charity regatta in numbers and dollars, Hospice Cup began in 1982 as an informal race among a small group of people interested in sailing and hospice care. Netting almost $28,000, the first Cup was amazingly successful—and fun! About 35 sailboats raced from Annapolis to St. Michaels on the Eastern Shore of Maryland. A few private power yachts carried sponsors and guests as spectators. All celebrated the occasion at a post-race party at a waterfront home, where trophies were awarded.