This picture and its companion, 'East Cowes Castle, the Seat of J. Nash Esq; The Regatta starting for their Moorings', similarly exhibited in 1828 and now in the Victoria and Albert Museum (repr. in colour by Reynolds in Victoria and Albert Museum Yearbook, I, 1969, p.69 pl.111a), were commissioned by the architect John Nash to commemorate the second year that the Royal Yacht Club held races at Cowes, and were based on the sketches painted while Turner stayed with Nash in 1827. At the sale after Nash's death in 1835 they were bought for 190 and 270 guineas respectively by the dealer Tiffin, in the second case almost certainly on behalf of John Sheepshanks whose collection passed to the Victoria and Albert Museum in 1857.

Most reviewers liked these pictures though there was a general criticism that the yachts were over-sailed, as for instance in the Repository of Art for June 1828: carrying such a spread of canvas in the channel in the like breeze would upset some of these yachts; but the canvas being Mr. Turner's they are safe; and perhaps the width of the sheet was necessary for pictorial effect'. Only the Morning Herald for 26 May was altogether critical, describing ‘The Regatta beating to Windward' as 'as far from Nature in its way as works showing Turner's more usual fiery and exaggerated colouring; ... the composition is a cold grey character throughout, particularly the part intended for the sea, which is more like marble dust than any living waters. The cutters of the regatta are quite out of drawing and just proportion.'