The foreboding, dark-gray sky looked ready to unleash a torrent of rain at any moment as I hustled along the bustling San Diego waterfront, trying to make it to CALIFORNIAN’s dock on time. It was hardly the weather I had expected when I packed my bag early that morning to race aboard the replica square-topsail schooner. The event was the 34th annual America’s Schooner Cup Charity Regatta, originally conceived in 1987 as a match race between the wooden-hulled schooners DAUNTLESS and BAQHEERA. It has grown over the years to become a celebrated gathering of West Coast schooners.