Michael Scantlebury, one of the conceptualizers of the event took the honors of winning the first Challenge.
The Philippine Hobie Challenge goes back to 1999 when a small group of international sailors envisioned an extreme sailing event that would take them to different islands requiring six days or legs traversing the open seas and camping in rustic areas. Thus the Challenge had its modest start in March 2000 with only five regional teams making the 190 nautical mile (380km) passage from Lucena, Quezon
to Boracay. The successful inaugural event proved the notion that the Hobie16 was rugged enough to survive long distance racing accross straights and passages only traversed by bigger boats.
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