Jolly Harbour Yacht club was founded in May 1993.  It's Founding Members were Geoffrey Pidduck, Hans Lammers and Dom Henry.

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In April on that same year the club hosted Antigua Sailing Week.

The Club then hosted the Carib Cup Regatta in 1995, 1996 and 1997 which were a great success.

The club started the Valentine's Regatta in 1996. The initiative was due to the impetus, motivation and encouragement of Antigua Yacht Club sailors and Robbie Ferron and Budget Marine which was intended to fill a void in CSA Calendar and to increase the Antigua Sports Calendar.

The Annual Regatta came into being after the Yacht Club lost the hosting of the Carib Cup when it was suggested that the winning island would take it over.

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The Annual Regatta takes place in November and the St Valentine's Regatta takes place on the weekend prior to the 14th February each year.

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The Club now runs Saturday afternoon sailing every week and both members and guests are invited to participate. We start and finish in Jolly Harbour with a variety of courses taking the participants out to Five Islands and around into Five Island Bay. Results and Prize giving takes place at 5.30 pm at The Out Out  Bar in the Jolly Harbour Commercial Centre.

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The Club also has a weekly meeting of members and friends at the Out Out Bar on Thursday evenings from 5pm to 7pm. Non and prospective members are encouraged to come along and meet club members and even find a boat to crew on during the Saturday racing.