
Base: the windward side, all three nights. Today starts at Kailua Beach Park, 526 Kawailoa Road, which has free public parking lots. From there you walk into Lanikai for the Kaʻiwa Ridge walk, locally called the Lanikai Pillbox hike: about 1.5 to 1.8 miles round trip, free, no reservation and no gate. Pace: one short, steep climb in the early morning, then an easy beach day.
Walk in from Kailua Beach Park
Park at Kailua Beach Park, not in Lanikai. Lanikai is a small neighborhood with a single road in and out. The City and County of Honolulu has put up “No Parking Any Time” signs along Mokulua Drive, and more limits are planned for Aʻalapapa Drive and the side streets. Tickets and tows are common, and rules on driveways, hydrants and unmarked sidewalks are strictly enforced.
From the beach park it is a flat 10 to 20 minute walk along Kawailoa Road and into the Lanikai loop to the trailhead on Kaʻelepulu Drive, across from the Mid-Pacific Country Club. There are no restrooms or water at the trailhead, so use the beach park facilities before you start. TheBus also loops between Kailua town and Lanikai if you would rather not walk.
The Kaʻiwa Ridge (Lanikai Pillbox) walk
The trail climbs steeply from the start on loose dirt and rock to the first of two old concrete military lookouts on the ridge. From the top, Lanikai Beach runs below you, and the two islets of Nā Mokulua sit offshore in turquoise water. On a clear morning you can see along the whole windward coast.
Allow 1 to 1½ hours. There is no shade, no railings and real drops at the edges, so stay on the main path and back from the cliff. Wear shoes with grip, carry at least a liter of water each, and use a headlamp if you go up in the dark for sunrise.
Expert tip: start the climb about 45 minutes before sunrise. The sun comes up behind the islets, the rock is still cool, and you are back at the beach before the parking lots fill.
Kailua Beach
Walk back to Kailua Beach for the rest of the morning. It is a long, wide curve of soft pale sand on a bay that is usually calmer than the North Shore, with the islets of Popoiʻa and Nā Mokulua in view. Swim, read, walk the sand together, and rest in the shade of the ironwood trees by the park.
Check the day’s surf, wind and water conditions before you swim. Trade winds can make the water choppy in the afternoon, and conditions change quickly. Use reef-safe sunscreen: Hawaii bans sunscreens with oxybenzone and octinoxate.
Kailua town for the evening
Where to eat: drive a few minutes into Kailua town for lunch and an unhurried dinner. The small town center has cafés, poke counters, shave ice and sit-down restaurants within a few blocks of each other, and it is a pleasant place to wander for an hour before dark.
Get to bed early. Tomorrow is a slower day, but the temple and the garden are quietest in the morning, and both close in the afternoon.
Base → Kailua Beach Park: about 5–15 minutes by car from Kailua or Kāneʻohe. Beach park → Kaʻiwa Ridge trailhead: about 10–20 minutes on foot. Ridge walk: about 1–1½ hours round trip. Kailua Beach → Kailua town: about 5 minutes by car.
Where to stay
- Paradise Bay Resort — a low-key bayfront resort on Kāneʻohe Bay, about 15–20 minutes by car from Kailua.
- A city-permitted Kailua B&B — or a small bed-and-breakfast in Kailua that holds a city permit; Honolulu limits most homes outside resort areas to longer-term rentals.
Dinner: in Kailua town; book ahead for weekend nights.
Tomorrow: Byodo-In Temple and Hoʻomaluhia, about 15–20 minutes by car.
Bad-weather plan
Rain on Day 1? Skip the ridge, which is slippery and steep when wet, and swap in Day 2: the temple grounds and the garden are fine in light rain. Walk Kailua Beach once the shower passes.
Stay: windward base · Anchor: the Lanikai ridge · park at Kailua Beach Park
Good to know: The ridge has no shade, water or restrooms, and no railings at the lookouts; turn back if it is wet or windy.





















