Even in season, Kailua is pretty deserted during the week. During the weekends locals descend on it, but otherwise, the long crescent beach is almost empty. It has astounding views at every step; there are ancient craters and an endless horizon to watch, with an occasional whale pod to discover if you stare long enough during the winter season.
What I like about Kailua is the absence of high-rises. This ultra exclusive beach area has no resorts or monolithic condominiums — just houses, some of which are mind-bogglingly expensive, others, more modest — but still more expensive than most of us can even imagine affording. Still, the whole feel of the place is casual. This is not a particularly showy stretch of houses and most are not hidden behind forbidding walls.
Some of them are actually available to rent. The ones directly on the beach have extraordinary price tags — but believe it or not, some of the ones within walking distance are affordable (you can find them on the internet). In addition to the beach you get a) bragging rights that you walked the beach that Obama walked (and rented on his Christmas vacation); b) the best shaved ice in the islands; c) access to a series of good to great restaurants; and d) a low-key town that makes you forget what a lot of other places in the islands have turned into.
My favorite memories on this last visit: devouring the tuna tower at Lucy’s; running amuck at Mama Yogurt’s tasting all the free sample flavors out of the do-it-yourself soft-swirl machines; having a marvelous dinner outside on the porch of the new Kalipawai Cafe restaurant, sister to its more famous sibling, the Kalipawai Market; strolling the beach in a light rain (and then watching it pour right after I made it into the house I was staying in); and just walking that gorgeous beach twice a day and thanking the fates (and my friend Deborah who opened up her house to me and several other friends) that have made it possible for me to enjoy such a beautiful and peaceful place.