Craggy Islands is the plot of land which was sold to Lewis, Simon, and Duncan by Hat Films. It is base of Hole Diggers Inc. which features in their series, Hole Diggers. From the beginning Simon preferred Lovely Island, which is the grassier and bigger island, which houses his iHoney StarPad. However, Simon still has a big presence at Craggy Islands. Because of this, he has recently built a link between the two islands.
Craggy Islands was expanded upon, with the foundations of the Big Aitch built by Lewis, the DwarfStar Alpha built by Simon and a pointless, yet visually pleasing, golf course built by Duncan. In the finale of Hole Diggers, Simon, Lewis and Duncan discover that the Dwarfstar was mining near their base, subsequently destroying Duncan's golf course and hotel which he built.