Wind Surfing
The island of Oahu has some of the best windsurfing spots in the world. Kailua, on the east shore, is a must go for anyone who windsurfs. Consistent trade-winds keep the sails taught year round. On the south shore there is diamond head. Catching wrap from the trades and great surf from the south this is the spot to if you want to get airborn. Go to windsurf or stay up top and watch.
The East Shore is by far the most popular place to windsurf on the island. If you're new to the sport don't worry. You can drive up to Kailua Beach anytime during the day and find a place to rent a board and take a windsurfing lesson. Guys are just hanging out in the parking lot in the backs of their old snap-on tool trucks loaded with boards and sails.
Diamond Heaad
The best spot to windsurf on the south shore is diamond head by far. The tradewinds whip in down the front of the crater and out to sea creating awesome power. Also a great surf spot, diamond heads waves make for an added bonus for experienced windsurfers to perform airial manuevers on the way out and catch so extra speed on the way in.
Kimberly and I haven't been windsurfing here but we do go surfing often. Most of the times there's at least one person out on a windsurfer zipping past us as we tireously paddle into the waves.
Hawaii Kai - Toes
The Hawaii Kai area is great for beginners although I haven't seen many people just hanging out renting boards. For both Kitesurfers and Windsurfers Hawaii Kai offers a very large at times very shallow bay with lots of wind off shore from the East. The surf break is pretty far offshore here and is choppy if you make it out. If you go here you have plenty of room to mess around and work on your arm strength and endurance. Be careful though, as I menitoned it can get really shallow at low tide and reef tends to stick out of the water.
Kailua Beach
Kailua Beach is the best known beach for windsurfing on Oahu and probably one of the best in the world. Year round tradewinds, a very large bay, and perfect weather create the ideal spot for windsurfers of all levels. Surrounded by reef about a quarter mile off shore the waters within the bay are calm enough for newbies. For those who know how to handle a sail moving to this offshore break will provide great waves for some uneblievable rides.
If you are new to windsurfing I suggest getting over to Kailua. Windsurfing in Hawaii is something you will not soon forget. As you travel on the only road into Kailua beach you will come upon a sweeping right hand turn. Just before this is a small strip mall that has two surf shops, both of which rent windsurfing boards. The rental rate goes for about $40 for 4 hours. We have tried to pay less for less time but have been unsuccessful, even on an overcast low crowd day. You may be able to bargain down the price, worth a try. Lessons are a littel more expensive running anywhere from $50 to $150. These are stringly recommended for a beginner. You'll have headaches if you don't.