The Little Britain Challenge Cup is the largest industry regatta for construction and property related businesses. Solent Events are a sponsor and official charter. Little Britain Challenge Cup, Cowes, Isle Of Wight, United Kingdom. likes · 4 talking about this · were here. Construction and property sailing. Sunsail are delighted to be a Silver Sponsor and Official Charter Partner of the Little Britain Challenge Cup, for the next 5 years. Enter the Little Britain Challenge. Saturday night is the spectacular gala dinner, and the event finishes on Sunday morning with a champagne breakfast before you head home! You'll also get the opportunity to claim overall honours. About Company Profile Why Choose Us Our Clients Testimonials Pricing Marina Locations. Little Britain Challenge Cup September Overview Itinerary Find out. This allows everyone to enjoy competitive racing at its very best with the your team's racing skills being the only factor separating your boat from the field.