The Funchal 500 Tall Ships Regatta and Festival do Mar 2008 was the centrepiece of year-long celebrations of the 500th anniversary of the first settlement on the Portuguese island of Madeira.
A fleet of 21 sail training Tall Ships gathered (10 - 13 September) in the historic port of Falmouth on the south west coast of England before racing to the Ilhavo (Port of Aveiro), Portugal (20 - 23 September). From there the Tall Ships raced to Funchal, Madeira for a Maritime Festival and major celebrations in the city (2 - 5 October).

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The Funchal 500 Tall Ships Regatta is organised by Tall Ships International Limited, a wholly owned company of Sail Training International.