Steve Black didn’t take to sailing until his mid-30s, but he quickly developed a passion for the sport and the lifestyle, and became an iconic figure in the sailing world. Black died of cancer on March 17 at the age of 71, leaving a legacy as founder of the Caribbean 1500, a pioneering bluewater rally for everyday sailors.

“Steve was all about inspiring people to break down their boundaries and do something they always dreamed about but might not have had the courage to do. That was what the 1500 was all about,” says Andy Schell, a delivery captain who with his wife, Mia, serves as event manager for the Caribbean 1500. “My favorite line of his, which he said at the skipper’s briefings before each 1500 start, was, ‘This is one of the last great adventures of our modern times.’ He truly believed that, and people followed him.”

Black’s long and varied career included stints running an educational publishing company, three years as executive director of US Sailing and managing the Sailing World National Offshore One-Design regattas in four regions around the country. Those who knew him best say his role as founder of the Caribbean 1500, which offered snowbirds a way to cruise to the Caribbean in the company of others, will be his most lasting legacy.

The impetus for the rally was Black’s observation that cruising sailors outnumbered offshore racing sailors, but there were virtually no organized events for cruisers. The Caribbean 1500 offered the chance to sail with other cruisers, combined with seminars taught by sailing experts, an SSB radio safety net, collaborative troubleshooting during the voyage, and plenty of fun and socializing.

For many, the 1500 remains a life-altering event that brings people back year after year. Although the “safety in numbers” aspect of the event drew the most attention, Black was most proud of its educational component and how veteran sailors readily took to mentoring less experienced ones.

Schell, who founded the education/adventure sailing company 59º North, remembers sailing his first Caribbean 1500 with his father in 2007. “Steve knew I was interested in expanding my horizons and getting some offshore sailing in,” Schell says. “I was working on the schooner Woodwind at the time in Annapolis, and he called to say that a berth was available on a Caribbean 1500 boat leaving from Charleston. My dad and I drove down that same day and sailed the next day, joining the fleet to Tortola. We were both impressed to see Steve on the dock with a bottle of champagne, despite us being the last boat to arrive — by over 24 hours. He really cared.”

Black retired from the 1500 in 2010 after 21 years and handed over management of the event — the longest-running such rally in North America — to the World Cruising Club. The rally has since been renamed the ARC Caribbean 1500. “The 1500 was never a business for Steve, even though it ran like one,” Schell says. “Steve ran the thing from the front, sailing on each event, and was a calming voice on the radio at each schedule.”

The 25th running of the Caribbean 1500 will leave Portsmouth, Va., in November and cruise to Nanny Cay on Tortola in the British Virgin Islands. www.carib1500.com

May 2014 issue