A rich history underpins the regatta's enduring appeal. While some records of its early years are incomplete, the longevity of the event is widely recognised, with the regatta surviving world wars, economic challenges, and even the recent COVID-19 pandemic. Despite these interruptions, the spirit of the regatta has remained strong, thanks in large part to the unwavering support of the local community and the dedication of its volunteer committee.

It offers a vibrant mix of beachside activities and entertainment designed to delight all ages. The day traditionally begins with a sandcastle-building competition and continues with beach sports, swimming races, and a lively market along the pier apron. Stalls, games and food vendors create a bustling atmosphere.

As day turns to evening, the celebration intensifies with live music, a community barbecue and family-friendly entertainment on the Esplanade. The event concludes with a spectacular firework display, lighting up the sky above Shanklin and drawing cheers from the crowds gathered along the cliff path and beach.

The regatta operates as a Community Committee Group, demonstrating its commitment to reinvesting in local life. Funding is raised through an official event programme, with strong support from local advertisers and businesses who contribute both financially and logistically. The involvement of volunteers, who give their time freely, is vital to the event’s ongoing success and community spirit.