About the Regatta

The Little Britain Challenge Cup is the property and construction industry’s annual sailing regatta.

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 Wharf Marina, West Cowes, organised in early September every year.  This year 2018 will be the 31st edition and will take place on Friday and Saturday 14th and 15th September.

The event is organised by a volunteer committee who work in the industry.


All the sailing takes place in the Solent around the ‘cans’ (the Solent buoys and marks).

There are 5 races held over two days – two on Friday and three on Saturday. In general, racing is from 9am to 4pm with lunch taken on board.

The racing is organised by the Island Sailing Club who are well known for organising the famous ‘Round the Island Race’.

There are two main classes: Racing and cruising. Racing is with a spinnaker and cruising is without.

Depending on the IRC rating of the boat, you are grouped into smaller classes so that you race with similar performing yachts.

Classes for one-design boats and sportsboat are organised, such as the popular Sunsail Match First 40s and J90s.

Many companies charter yachts and some bring their own. Boat lengths range from 25ft to 55ft and the average is about 40ft.

The Little Britain Challenge Cup winner is the class winner with the best overall score.


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.


The regatta raises thousands of pounds for sailing charities doing great work, such as the 1851 Trust – the charity of Landrover BAR – Ben Ainslie Racing’s America’s Cup team, The Ellen MacArthur Cancer Trust and the Cirdan Sailing Trust plus a host of smaller island sailing charities. Surplus profits and donations are shared between the charities and over the past 30 years the Little Britain Challenge Cup has raised over £1.25 million.


The cost to enter a boat into Little Britain starts at £795 + vat. A budget guide is included in the Entry Brochure which includes costs for chartering, food, accommodation and crew clothing. You will notice most of the costs is for boat chartering.


Subscribe, see form below, read the Notice of Race (NOR) , and complete your entry on  the online Entry System.
Provide your company details, and pay the entry fee.  Boat details and crew details can be added later when you know them.

Organise your boat, your crew, hull graphics, crew clothing,  accommodation, and lunch and suppers.

Go sailing !

Should you have any questions please email info@littlebritain.co.uk