By Phil Dickey
Oakcliff Sailing, a nonprofit sailing organization based in Oyster Bay, New York, has entered seven of their boats in the Newport Bermuda Race starting June 17th. Leading the effort is Dawn Riley, a member of the U.S. National Sailing Hall of Fame and executive director of the organization, which in the 12 years since its founding has proven to be a bona fide “sailing university.” The fleet includes a water-ballasted maxi Z86 OC86 (formerly Windquest), JV 66 Numbers, Ker 50 Temptation, and four Farr 40s (Blue, Red, Black, and Gray).
Dawn will likely sail on OC86 with 19 other sailors, including Oakcliff trainees and graduates, along with selected coaches. As in 2018, Oakcliff board member Art Santry will skipper Temptation, with a crew that will include Oakcliff sailors. Numbers will sail as a charter with a crew of Oakcliff trainees and graduates.
Veteran UK navigator Libby Greenhalgh, who sailed in The Ocean Race and the Volvo Ocean Race (team Scallywag, 2017-18 and SCA 2014-15), and the impressive young South African ocean racer Michaela Robinson will lead an all-female crew of eight high school students from Lincoln School in Providence, R.I., to Bermuda in Farr 40 Blue. They have been training intensively for the race for over a year.
Eight Canadian sailors, known north of the border as “Yard Sail,” will take Farr 40 Red, with two Oakcliff coaches onboard. A U.S. Coast Guard Academy team, also with Oakcliff coaches onboard, will sail Black. An all-Oakcliff team will sail Gray. And every boat will have female sailors onboard.
Dawn says, “The Bermuda Race is the ultimate distance race on the East Coast,” which is why she’ll send 69 sailors at an average age of 29 down the 635 nautical mile course—30 women and 39 men. On the Farr 40 Blue, the average age will be 23, including the coaches.
Oakcliff provides a unique opportunity for sailors who want to improve their skills. Trainees can live on site in an America’s Cup-style facility, which offers dormitory accommodations for up to 43 sailors. They pay tuition and learn by doing—maintaining Oakcliff’s fleet, learning rigging, electronics, fiberglass, and composite work, yachting management, and other marketable skills that benefit those who want careers in the marine industry. Other sailors come simply to improve their skills on the water.