Regattas & events

Little Britain Challenge Cup

11 Sep 2020 - 12 Sep 2020

Paul Wyeth

The property and construction industry annual regatta

The Little Britain Challenge Cup is the property and construction industry’s annual sailing regatta. It brings together hundreds of people from the industry to sail, socialise and fund-raise. Little Britain attracts project teams celebrating success and companies looking to team-build and entertain key clients.

Since its foundation in 1988, the regatta has attracted hundreds of companies and thousands of crews, and for many it remains one of the best, most enjoyable and memorable networking events in the industry.

It is a fantastic event for project teams celebrating success, for team building and relationship building, and for client entertaining. It’s also a great time to learn to sail with other industry professionals and to improve your boat and racing skills.

Little Britain is a two-day regatta, based at Shepards Marina, Cowes, organised in early September every year.


At the end of racing each day, everyone meets up on the pontoons or at the marina bar for drinks. Good food is provided and meal tickets need to be ordered in advance. Some crews go into town to the pubs or restaurants but everyone returns later for drinks to meet up and finish the day with some light entertainment.

Live music is played each evening. There’s always a fantastic atmosphere with plenty of opportunities to catch up with industry friends. The regatta bar closes at midnight on Friday and 2am on Saturday.

Many crews sleep on their boats and use the marina’s new washroom facilities. A good percentage stay at the local B&Bs, hotels or rent ‘crew’ houses nearby.

For further information on this event visit

Do you need accomodation for this event?

Talk to us on +44 (0)1983 300071

Alternatively email us at