The flights are booked - late July for a few weeks. What the chance of getting a sail that time of year? Should I head north or south? What's gear hire like? Does my butt look big in these pants?

and never wear shorts over a wetsuit.

NO.
Stay home, come back in Dec.

unfortunately, family trip (son catching up with Nana & Pa) first but scoping it all out for future trips..

Had a great trip and scoped out the spots. Saw Hardies, Pelican, Pt walter saw all the ocean beaches. Had a beer and a burger at the endeavour tavern Lancelin. Your spoilt by the amazing sailing places so close to the city. Not a breath of winds but beautiful weather. Shorts and t shirt for the first week and that was down south!

Had a look at some employment opportunities but I didn't find an ice coffee that I liked so will have to think about it....