Kailua

Kailua sits twenty minutes from Waikiki through the Nu’uanu Pali tunnels, and the drive alone is worth the trip — you go from Honolulu’s high-rises into rainforest into, suddenly, a beach town so quiet and low-slung it feels like a decade Waikiki left behind.

The Beach That Ruins Other Beaches

Kailua Beach is consistently ranked among the best beaches in the country, and for once the ranking undersells it. The sand is fine and pale, almost cool underfoot even at noon, and the water sits in that impossible turquoise that photographs always seem to oversaturate but don’t. Lia and I rented kayaks from a shop a few blocks off the sand and paddled out to the Mailuna — locally the Mokulua Islands, two little volcanic humps just offshore — where you can beach the kayak on Moku Nui and have what amounts to a private cove for an hour before the next group arrives.

Lanikai, and the Steps Everyone Climbs

A fifteen-minute walk south along the coast road gets you to Lanikai Beach, technically a separate stretch of sand but continuous with Kailua’s, backed by beach houses instead of a public park. The Lanikai Pillbox hike — an old WWII bunker on the ridge above — is short, steep, and absurdly crowded at sunrise because everyone has read the same three articles telling them to go at sunrise. We went at 4pm instead, caught the light going gold over the Mokulua Islands from above, and shared the pillbox with maybe six other people instead of sixty.

A Town, Not a Resort Strip

What sets Kailua apart from Waikiki isn’t just the beach — it’s that Kailua Town, three or four blocks back from the sand, is an actual neighborhood. Kalapawai Market has been the corner store since 1932, and I got in the habit of stopping there most mornings for coffee and a malasada before the beach. There’s a Sunday farmers market, a handful of genuinely good poke counters, and almost no chain hotels — most visitors stay in vacation rentals in converted beach cottages, which keeps the whole town feeling residential rather than built for tourism.

When to go: May through September brings the calmest water and the least wind, ideal for kayaking to the Mokulua Islands. The trade winds pick up October through April, which locals actually prefer for kitesurfing and windsurfing off the bay.