Winter is North/East shore stuff, so forget Poipu area unless you hate rain, like to drive, and like small waves.
Stay at Hanalei if you can afford it, Princeville, has a couple of big destination hotels...expensive, of course, but a walk to Hanalei (right), and Middles (outer left). Within 10 minutes is whysoslow, Tunnels, Cannons (Pipe of Kaui), forget Anini/Kaliewia area unless you are already local. If the swell at N Shore is tiny (too small to surf even for you), you can get some NE swells that hit WestCoast around the Kapaa area, beachbreaks.
If you KNOW a W swell is coming, you can try the S Shore Air Base spots, but likely Hanalei to Napali will get something.
Hike end of the road Napali Coast, bring water, Tevas, swim and waterproof light clothing. Flat conditions preferred, good diving.
Anini Beach teachs beginner winsurf lessons, protected bay about shoulder deep.
Heli rides over Napali Coast might cost $70, but everyone says it's worth it before hiking in.
Yak ventures up Hanalei River..kinda boring, but if you've never done it, and serious sea yak ventures out past Haiku....
You know jyourass is park was filmed there.
Good tidereefs between Hanalei and Anini.
I'm not a waterfall fan, as they get crowded touristy early.
Can't miss fun, check Poipu (shopping) but it faces S.
