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Jonathan Cheshire - Sail Training International
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Meet the team

Jonathan is a leading social entrepreneur and developer of charities, with particular expertise in employment and training, outdoor education, and young people’s issues. He has started and led several charities addressing homelessness, employability, and disadvantaged youth.

Until 2014 He was founder and CEO of Wheatsheaf Trust, a charity promoting social inclusion and economic development. From 1989 to 1996 he was National Director of Ocean Youth Club, at that time Europe’s largest sail training organisation.

Until recently, he was Chair of Solent University and Hampshire & Isle of Wight Community Foundation and Vice-chair of Street Kids International. He was also a Trustee of the Association of Sail Training Organisations until 2018. He has won a number of awards for his work on employability and social enterprise.

A keen sailor and oarsman, he rowed for England in 1969 and sailed across the Pacific in 1978. He is married with two adult children.

Relive the Races

Use YB satellite tracking to relive all the action during The Tall Ships Races 2023 and The Tall Ships Races Magellan-Elcano...

The adventure starts here

Visit our sail on board site to go sail training