Great sailing together






About the Regatta

The Little Britain Challenge Cup – the property and construction industry’s annual sailing regatta – is a two-day, 5-race series event organised by volunteers for the industry.

IRC boats, sports boats, boat owners, and Sunsail 41.0 one design boats are all welcome.

The regatta is dedicated to raising money for sailing charities who have been heavily affected over the past year as their funding channels have dried up due to the social and working restrictions caused by the COVID 19 pandemic.

This year’s regatta will be held in West Cowes, and racing will be on the Solent, around the cans, with courses set in both the east and west of central Solent.  There will be plenty of opportunities to meet up with crews, friends and industry colleagues during the pontoon parties and at the Royal Ocean Racing Club in Cowes.

The LBCC committee can assist with local professional yacht chartering and can recommend crew accommodation in town.  Everything you need for provisions can be found in shops on the high street which is only two minutes walk from the marina.

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 usually a two-day regatta, based at Shepards Wharf Marina, West Cowes, organised in early September every year.  In 2020, due to restriction caused by the pandemic, the 33rd edition was a one day event, held at Port Solent by Sunsail Events. In 2021 we returned to a two day event and had a fantastic regatta with over 300 guests attending.

We hope to host over 40 boats and 400 crew this year from Cowes.

The event is organised by a volunteer committee who work in the industry and is the reason why we are able to keep participation costs low as well as donating significant surplus’ to charities but we could not do this within the support of the industry and the love of sailing.


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

For this year’s regatta there will be 5 races over two days and they will be held on Friday and Saturday 9th and 10th and September. The first race starts at 1030h with lunch taken on board between races 2 and 3.

The racing will be organised by the professional race committee from the island.

There are three main classes:  IRC class racing with spinnakers, IRC Cruising without spinnakers, and one design match racing fleet from Sunsail.

Depending on the IRC rating of the boat, and the number of boats entering, you may be grouped into smaller classes so that you race with similar performing yachts.

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.


This year,  we will have pontoon parties, and will organise them to work within any restrictions.

Live music is played each afternoon and there’ll be a fantastic atmosphere with plenty of opportunities to catch up with industry friends.

Many crews sleep on their boats and use the marina’s new washroom facilities but a good percentage have worked out that it’s very comfy at the local B&Bs, or renting ‘nice crew’ houses nearby.


The regatta raises thousands of pounds for sailing charities doing great work, such as  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 35 years the Little Britain Challenge Cup has raised over £1.5 million.


The cost to enter a boat for the two day regatta is from £995 .  You can charter from Sunsail or from reputable charter companies around the Solent area.


Subscribe, see form below, read the Notice of Race (NOR) , and book your entry via the online booking, registration v-office – Ok. it’s a form

Provide your company details, and pay.  Boat details and crew details can be added later when you know them.

Organise your boat, your crew, hull graphics, crew clothing,  and any accommodation.

On the day, get your breakfast bacon butties and pack lunch from the great cafes on the high street, at M&S or Sainsburys, and you’re all done and ready to have fun.

Go sailing !

Many crews arrive on Thursday evening, berth at the marina, sort out accommodation, and meet everyone in the Anchor and the Island Sailing Club for a great evening out.

Should you have any questions please email

It’s plain sailing, but we are always happy to help.