Ocean Cruising Club

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Lt Col Ewen Southby-Tailyour OBE

s/v Black Velvet

For his role as the driving force behind the Jester Challenge

It is without a doubt that Lieutenant Colonel Ewen Southby-Tailyour OBE embodies the spirit of the Jester Medal. Ewen was nominated for his role in managing the Jester Challenge, writing the biography of Blondie Hasler and inspiring many to sail long-distances in small boats for the first time. In fact, more than one nominator indicated that he is “the driving force” behind the Jester Challenge and has done much for the cause of singlehanded sailing, inspiring and encouraging many to attempt and achieve what they previously thought to be impossible. Ewan, in his unique and ever jocular way, has contributed greatly to its success and, by definition, to many individual success stories.

Ewan is an author, sailor, and retired Royal Marine Commando who served for 32 years in the Royal Marines specialising in amphibious vessels from all the NATO countries before retiring with the rank of Lieutenant Colonel. A veteran of the Falklands War, Ewen went on to write several books on the commando’s point of view in conflict. Ewen went on to take over the responsibilities for the Jester Challenge, now a well-known and regular event in the sailing calendar.

The Jester Challenge is run on a ‘gentlemanly basis’ within the following guidelines:

- for sailing vessels between 20 and 30 feet (including multi-hulls)
- human power is the only acceptable alternative propulsion to that of the wind: rowing or clubhauling, for instance, are permissible
- single-handed to Newport Rhode Island
- one way
- stops allowed
- no time limit.