Turner revisited the Isle of Wight in late July and August 1827, staying with the architect John Nash at East Cowes Castle. In an undated letter he asked his father to send one or if possible two pieces of unstretched canvas, either a piece measuring six by four feet or a 'whole length', and it was on a six by four-foot canvas, cut into two, that he painted these nine sketches. The two rolls of canvas were rediscovered at the National Gallery in 1905 and divided into separate pictures. One roll contained Nos.311, 313, 315, 318 and 319, the other Nos.312, 314, 316 and 317. No record was made of the placing of the sketches on the two rolls on canvas, but to a certain extent this can be reconstructed. On the first roll the two largest sketches, Nos.315 and 313, were one above the other, flanked on the left by Nos.318, 311 (both upside down) and 319. On the other Nos.317 and 314 were at the top, Nos.316 and 312 below; No.312 was definitely to the right of No.316, and No.317 seems to have been above No.316.

It has been suggested that at least some of these sketches were painted on the spot (Graham Reynolds in Victoria and Albert Museum Yearbook, I, 1969, pp. 6772), though the practical difficulties, especially when out at sea, would have been considerable. It is interesting that the three sketches for ‘The Regatta beating to Windward' seem to have been painted alternately on each roll, No.311 on the first, No.312 on the second and No.313 again on the first; this could have been to allow an assistant time to adjust the roll for a new sketch. The 'Windsor and Cowes' sketchbook contains drawings of boats racing, boats stationary, views of the coast and figure studies, though none directly related to the oil sketches, which to a certain extent supports the suggestion that they were done on the spot. It also contains a list of the boats with their names, the names of their owners, and their colours, showing just how detailed was Turner's interest in the Regatta (T.B.CCXXVI-80v; see No.302).

The two groups of sketches of the Regatta were used for the pictures commissioned by John Nash and exhibited the following year (see No.321). The other three are of three different subjects. 'Between Decks’ may be just a scene of visitors on board the naval guard ship that can be seen in the background of Nos.31I-313 though it may reflect the practice, at least up to about 1805 if not later, of accommodating sailors wives between the upper and lower decks when a ship was in port. The 'Study of Sea and Sky', in which the distant coast can just be seen on the horizon, may well be Turner's first oil painting to concentrate on these two elements; it hardly prepares one for the stormy seapieces to come (see Nos.490-506)! The smooth handling contrasts strongly with the vigorous sketches for "The Regatta beating to Windward', but with 'Shipping off East Cowes Headland' one returns to a mood of exquisite calm.