- Offshore Sailing School
When Steve Colgate raced from Cuba to Spain at 19, he dreamed of making a living by sailing. Today, at 70, with seventeen transatlantic crossings, eighteen Newport-to-Bermuda races, an Olympics run, and two America’s Cup trials to his credit, he does indeed pay the rent by working the sea. But perhaps the thing that he and wife Doris are proudest of is the Offshore Sailing School. Opened in 1964 on City Island, it uses the training boat he designed—the Colgate 26—that’s since been adopted by the Naval and Coast Guard academies. This summer, he’ll give lessons out of Chelsea Piers, Fort Schuyler, and Liberty Landing. The beginners’ classes are limited to four students per boat—adults or kids—over three daylong sessions, almost all spent on the water ($695 to $895). He teaches advanced classes as well—see his Website (offshore-sailing.com) for details and fees—and runs a club for experienced sailors sans boats (dues, $1,295 per year).