Ascend the iconic red-dirt Lanikai Pillbox Trail at sunrise for a panoramic ridge-top reward — twin WWII bunkers framing Lanikai Beach, the Mokulua Islands, and the emerald Ko'olau Range in one breathtaking sweep.
What to expect
Your expert guide meets you at the Kaelepulu trailhead in the pre-dawn cool and sets a steady pace up the steep, switchbacking trail as the sky blushes pink over the Pacific. At the first pillbox, the Mokulua Islands emerge from the mist like emerald jewels; at the second, a 270-degree panorama of windward Oahu unfolds. The guide narrates the WWII history of the concrete bunkers before leading a safe descent in time for a local breakfast recommendation in Kailua town.
Good to know
Trail is 1.8 miles round-trip with 600 ft elevation gain — moderate fitness required. Departs ~5:30 AM for sunrise; back in town by 8 AM, well within any all-aboard window. Wear trail shoes, bring water, and pre-arrange transport with the operator.
Sail there
Luxury cruises that call at Kailua — book through us, the fare is identical and your concierge stays on your side.
More to do in Kailua
- Kailua Bay Kayak & Lanikai Islet Eco-Adventure
- Byodo-In Temple, Ho'omaluhia Gardens & Windward Oahu Private Tour
- Maunawili Falls Jungle Hike: Hidden Waterfall Deep in the Ko'olau
- Kailua Farmers Market & Artisan Food Tour of Kailua Town
- Lanikai Beach Luxury Private Sail & Snorkel at the Mokulua Islands