Windward Oʻahu sits at the center of one of Hawaiʻi's turning points. In 1795 King Kamehameha I landed on the island and won the Battle of Nuʻuanu in the cliffs above Honolulu — the victory that brought Oʻahu under his rule and all but completed the unification of the Hawaiian Kingdom. In the century that followed, missionaries built churches and planters laid out farms along the windward coast, yet Kailua stayed rural and Hawaiian at heart: a district of taro, cattle, and fishing, far from the harbor town growing up on the leeward side at Honolulu.
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.
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.
