A classic topic for windsurfers, the Travellers Lament. Or the Curse of the Airline Checkin.
Sounds like a great trip proposal, but also speaking from many ugly experiences, a quick tally of your equipment wishlist above takes us over 4 x23kg of equipment alone inc the inevitable "etc" (mast base/s, extns, fins etc) - this stuff adds up + FAST.
That's without allowing for clothes - and no real allowance for bag weight/s.
See if you can select an airline with a "user friendly" sporting goods baggage policy(getting VERY scarce these days - many used to exist, but these days drying up quicker than Global credit). If that fails, take a look at airline privilege membership (not the free Frequent Flyer miles but a paid membership to some airline “bonus” program eg Qantas Club; which often include extra baggage allowances and often(sometimes!!) ensures a softer enforcement of the cash register at the checkin scales…
You can then wine+dine in the Club Lounge to celebrate your checkin success ( or drown your sorrows )preflight at their expense either way, included ! Joking ! (but only half!)
Road freight : Pack/ship by truck a mix of clothes and equipment in advance. Hasn’t been seen to work on to many international trips especially involving crossing water though! Works best as an out+back travel mode, not effective for ongoing multistop trips.
Rental : arrange to rent some (or all) of your equipment at destination/s. Again, many variables apply as to viability and doesn’t sound ideal compared with using your own well fitted and tuned gear but many times we have seen the rental option emerge as nowhere near as “bad” once many/all factors are considered, inc airline and transit damage, which seems to prevail on heavily loaded and minimal packed oversize bags. (try it !)
Last one : Good Luck ! Seriously, in the end - these days - it really does start to count. A lot .
Cheers ~ Ian