Alive
The question is not what or how ... The event you point to and Roland's Gold Cup series were very succesful. But they were not sustained... Why?

The problem is that many of the historic regatta's suck ... and offer no opportunity to market sailing by doing these kinds of things. These events are not going away because they are part of the ISAF and Corinthian sailing culture. ISAF would have to sanction or invent these new gran prix events and push the old regattas back to their Corinthian roots.

So... Does ISAF have the vision and skills to do this reinvention .... OR do you try to build this elite racing circuit apart from ISAF?

Here is an example of how the program is mixed up in the US... the Miami Olympic Class Regatta, or OCR is the only ISAF grade 1 event. Should my neice be able to register and go race on her laser? Should a hacker like me be allowed to compete just because I owned a Tornado. (The standing joke was who would rise to the top of the Kiddie pool)

The ISAF sanctioned grade one event is just a multi class one design regatta.... If you own the boat.... pay your US Sailing dues and go! What is special about that?

Look at golf or NASCAR racing... they have qualification series that you need to succeed at in order to make the big show. Scarcity focus'es the mind... Look at qualifiying for a worlds in a popular class.... It is much much more intresting to the competing sailors and the sailing fans.

This is a tough political problem... The people running the classic Corinthia regattas will not want to loose their ISAF cachet... but ... these are the same people you will need to put on the ISAF Gold cup events in windy locations.