Hey Julzt,
Over the two seasons I spent there, I mostly rode Kailua Bay (close to work) which offers a wide variety of water conditions all fueled by the local trade winds which blow anywhere from about 13 to 18 knots and sometimes to around 20. Probably best average is around 15-16 knots.
Water conditions are : Flat water up near the boat ramp at Lanikai Point and around Flat Island. Small chop in front of the launch area. Waves out the back on the reefs, anywhere from waist high to overhead in storms. Cross onshore waves at Castles which is across the bay towards the marine base.
As Jeremy said, there is a heavy political battle constantly ongoing, so it is necessary to play by the rules and be super courteous. There is only one launch spot unless you go down and launch near or in front of Robbies place.
A nice friendly peanut gallery when you get to know everyone. Great food (Deli sandwiches) and drinks from the Kalapawai General store.
Other alternatives are kiting in Kaneoae Bay (next one around from Kailua Bay). Launch is from a small place near the Chinamans Hat, accessed from scenic the coastal road up north. You can also kite Goat Island but watch for break ins in your car, especially if you drive a rental.
Driving up the freeway to the north gives you access to Mokulaiea which can be a world class spot of strong wind (20-25 knots) and fun waves in a side shore orientation. You will need a car to get there as its nearly an hours drive from Kailua. Definately worth the trip as it is up there with the best spots on the planet when it's really "on". Avoid weekends as it's too crowded, but weekdays are awesome.
There is also a spot called Barbers Point which I planned on doing but never got around to. Seldom kited but reported to be awesome on a good day.
In Kona winds (opposite direction), you can kite the other side of the island ie around Waikiki, but this us usually in their winter. There is also another spot starting with H that I can't remember which can also be really good but it can also be quite shallow with coral bottom and rigging can be an issue as it is in an affluent area and there is only really one place. Hook up with a local to take you there if the wind is the right direction. I only kited there several times so have only vague recolection of names and how to get there.
Hope this helps. Search "Kailua Vacation Rentals" for accom as there are no hotels or resorts in Kailua, just private rentals. All the night life and shopping etc is in either Waikiki or Haliaewa (surf town near Waimaeia, pipe and sunset).
Hope this helps,
