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After the first Festival, the Victoria Real Estate Board (VREB) considered this to be a community event worthy of ongoing Board sponsorship. The VREB continued to grow the Festival to include a Welcoming Reception, over 30 awards, a dozen judges, a formal Awards Banquet, Classic Open Sail and Schooner Cup Races, and the Sunday Sailpast – all of which are still part of the Festival today.

After two decades of independent sponsorship, the VREB welcomed a new sponsor: the Times Colonist (1998 – 2000).