Kailua stayed country until the middle of the twentieth century. After the war, new roads over and through the Koʻolau opened the windward side to Honolulu, and through the 1950s and 1960s Kailua filled in as a leafy bedroom community of schools, churches, and beach bungalows. Tourism mostly went the other way — to Waikīkī — which left Kailua delightfully local and let its beaches keep their easy, unhurried feel. What did draw the world was the wind: the same steady trades that cool the town make Kailua Bay one of the great windsurfing and kitesurfing waters anywhere, and the sport's early champions made their name on this very water.
Kailua's name means ‘two seas,’ for the two currents that meet across its broad windward bay, and people have lived along that bay for many centuries. Native Hawaiians settled the fertile lowland behind the beach, farming taro in the wetlands of Kawainui — the largest ancient marsh in the islands — and raising fish in walled coastal ponds. Above the marsh still stands Ulupo Heiau, a massive stone temple platform whose terraces were laid by hand long before Western contact and are preserved today as a state monument. This was rich, settled country: water, fishponds, taro, and a sheltered bay, all held in by the green wall of the Koʻolau Range that rises sharply behind the town. From the water it is an unmistakable place — a wide blue bay, a green ridge, and a low, fertile plain in between, the kind of setting that draws people and holds them.
Why People Visit Kailua
Kailua blends scenic windward beaches with deep Hawaiian heritage. Visitors come to swim, paddle out to the islands, and hike to a pillbox view, then slow down in a town that stayed local. It is picturesque, approachable, and meaningful to the island families who call it home — natural beauty and everyday culture side by side, with year-round appeal in its parks, paths, and shoreline.
