Kailua Things to Do Tips by AKtravelers Top 5 Page for this destination

Look for Instant Waterfalls in the Cliffs

This is the view from the yard of my house in the Maunawili section of Kaiklua. Normally, I never saw waterfalls, but after an especially heavy rains they magically appeared! In fact, you can usually count on waterfalls after heavyu rains, but you have to be lucky enough to have the clouds lift to see them. Drive to Maunawili or through the tunnels on the H3 tyhe next time you get a heavy, persistent rain that covers the entire island and you'll be stunned! I estimate this happens about 5 times a year, so you have to be lucky.

Lanikai or Kailua Beach? Tough Choice

When you're in Kailua, you have the choice of two beaches that are rates #1 in different publications as the best beach in America. As of this writing, I favor Lanikai Beach, which is just south of Kailua beach and used to be connected. There's less sand but the view of the Mokolua's really takes our breath away. If you've seen pictures of bathing suit models whiling away the time with islands off the coast, chances are you're looking at Lanikai Beach. The sand is the softest, whitest around and the surf is virtually nonexistent.
...Kailua Beach offers slightly rougher sand but a playful body surfing are near Kalama Beach park. It's wider, longer and less crowded than Lanikai, and you're less likely to get a parking ticket. Kailua Beach is where the Obama family chose to spend their Christmas right before their inauguration, so it stands up pretty well to most competition. If you have a chance visit both of these jewels.

Climb Mount Olomana; It's Awesome!

Climbing Mount Olomana is one of the best short hikes on all of Oahu, but I'm putting it on my Kailua page because the only people we met on the hike were all from the Windward side, so it's apparently not of interest to the mainstream Oahu visitor. Good news for you if you like hiking and you've stumbled on to this tip.
The hike is 3 hours round-trip, and starts after the gate at Luana Hills golf course. After a gradual decent through forest, you start finding that you'll need to use the ropes (already there) to hoist yourself over rock formations or up rock cascades. It'sreally quite fun, though if you don't like heights you may cringe at some of the exposed rock scrambles and narrow knife-edged ridges near the top. However, the views are excellent -- a 360-degree look at the Windward side!
By the way, this hike was actually written up in the New York Times, so don't only go based on my recommendation.

Website: http://www.summitpost.org/mountain/rock/151222/mount-olomana.html