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The Barcolana Regatta 2010. The Barcolana Regatta Or Autumn Cup Is An Historical European Sailing Race Born In 1969 Thanks To The Societã Velica Di Barcola E Grignano Of Trieste. It Takes Place Annually In The Gulf Of Trieste, Every Second Sunday In October, Being One Of The Largest Sailing Races In The World With Over 2000 Participants