A long, graceful bay protected by a coral reef is Kailua’s delight. The nearly 4-mile-long stretch of ivory sand is made for strolling, and the weather and wave conditions can be just about perfect for swimming, kayaking, windsurfing and kitesurfing. None of this has gone unnoticed. Decades ago expatriates from the mainland bought up cottages crowded into the little neighborly lanes; the ones near the beachfront were often replaced with megahouses. South along the shore lies the exclusive enclave of Lanikai, with million-dollar views – and mansions to match.
In ancient times Kailua (meaning ʻTwo Seas’) was a home to Hawaiian chiefs, including, briefly, Kamehameha the Great after he conquered Oʻahu. Today it’s the Windward Coast’s largest town, where you’ll find the vast majority of the coast’s restaurants and retail. This is the place for a day trip from Waikiki or a weeklong pleasurable idyll.