Anaehoomalu Bay is great for windsurfing, especially in the afternoon when the wind picks up. This beach is very casual & many try the water sports available even if it's the first time. There is no pressure here to 'look good'. Anaehoomalu Bay is the only spot on the island where you can learn to windsurf.
I realize this tip should be under the Sports category but this was created before the category existed.
Lanikai Beach is one of the world's top 10 beaches and is great for kayaking, swimming or wind-surfing. Walk the sand at sunset and then have a Mai Tai at Buzz's Steakhouse which has a Banyan Tree growing through the middle of the restaurant.
Fondest memory: My favorite thing about Kailua is seeing the vista of the small seaside town as I'm coming home from work in the 'big city' of Honolulu. While much of Hawaii has been overbuilt, Kailua's beauty remains untarnished by modern day 'improvements'. All of the days cares just wash away when I see Kailua.
You have to try to go surfing at Pyramid Rock or North Beach on the Marine Corps Base. Get someone who lives on the base to get you on cause you can't get on without a sponsor. But it's the best surf spot on that side of the island.
Fondest memory: EVERYTHING WEATHER WOMEN SCHOOL BBEEAACCHH>>>>>>>>
Favorite thing: Aqua-bikes or kayaks are available for rental. Another good way to soak up the sun and burn a few calories. Don't forget the sunblock.