‘There are the haves, and the have yachts.’ This increasingly popular saying highlights the distinction between the merely rich and the super-rich. As this phrase implies, sailing has traditionally been viewed as a bastion of extreme wealth and privilege. There is much truth to this view. In its most extreme manifestations, sailing (or ‘yachting’) continues to attract – indeed require – extravagant wealth, a mercenary approach to recruiting the best talent, and an arms race-like pursuit of technology-enabled comparative advantage. There are many manifestations of this super-elite variant of the sport, including but hardly limited to the America’s Cup. Nevertheless, the sport also grew dramatically in the post-Second World War era to reach a much wider (if not quite mass based) community of participants. This process of ‘democratization’ occurred through the rapid growth of relatively small one-design classes driven in part by the advent of ‘DIY’ (do-it-yourself) designs focused on greatly simplified construction techniques with the potential for homebuilding and, more recently, a ‘Fordist’ trend towards manufacturer-based and mass-marketed classes. Geographically, the sport’s diffusion has partly reflected the persistence of local and regional conditions and communities, and partly resilient (post-) colonial and geo-strategic dynamics. Ironically, this trend toward ‘massification’, along with the growth of ‘lifestyle sports’ like windsurfing and kite-sailing, has led to ongoing diversification of, and splintering within the sport, effectively diluting its popular reach.