Start from 37 curated places around Kailua, HI, then choose the recommendations that fit your guests.
Restaurants & cafés
Cinnamon's Restaurant
A Kailua institution for breakfast and brunch, Cinnamon's has earned a devoted following for its guava chiffon pancakes — fluffy towers with a tropical sweetness that Time Out named among the best in America. The eggs benedict variations run from classic to kalua pork to mahi mahi, all served in a warm neighborhood-cafe atmosphere. Weekend waits are long and worth it.
Over Easy
The newer brunch contender that's won over serious locals with its Kailua hash, creative egg sandwiches, and coffee serious enough to justify the visit on its own. The space is small and casual, portions are generous, and the menu changes often enough to keep regulars coming back. It runs a tighter, more focused operation than most breakfast spots in town.
Trails & outdoors
Ka'iwa Ridge Trail (Lanikai Pillboxes)
The most popular sunrise hike on the windward side — a short, steep scramble up a ridgeline above Lanikai that deposits you at two World War II military bunkers with panoramic views of the Mokulua Islands, Kailua Bay, and the Ko'olau mountains. It's only 1.7 miles out and back but has sections steep enough to require hands on the ground. The payoff-to-effort ratio is among the best on Oahu.
Kawainui Marsh Trail
A flat, paved 2.8-mile loop atop a flood-control levee through Hawaii's largest remaining freshwater wetland, with unobstructed Ko'olau mountain views and excellent endemic birdwatching. It's accessible to all fitness levels and the wide path accommodates joggers, cyclists, and strolling families comfortably. The early morning light on the mountains and the stillness of the marsh make this a genuinely lovely walk.
Things to do
Kailua Beach Adventures (Kayak & SUP Rentals)
The only kayak rental outfit within walking distance of Kailua Beach, and the essential gateway to paddling out to Flat Island or the Mokulua Islands. The shop stocks single and tandem kayaks, stand-up paddleboards, snorkel sets, and bikes, with guided tours available for those who want a local to lead the way. Straightforward, well-run, and central to the Kailua experience.
Kaneohe Bay Sandbar Tour
A natural sandbar in the middle of Kaneohe Bay that emerges at low tide to form a white-sand beach in the middle of the ocean — one of the most surreal natural experiences on Oahu. Tour operators like Captain Bob's run catamaran trips that include snorkeling the bay's pristine coral, a grilled BBQ lunch on the sandbar, and beach volleyball. The reef here is in far better shape than Hanauma Bay.
Landmarks & sights
Kailua Beach Park
Three miles of powdery white sand curving around turquoise Kailua Bay, consistently ranked among Hawaii's best beaches. Trade winds keep things breezy and cool, making it the island's prime spot for kite surfing and windsurfing. The water is calm enough for families and paddlers, yet the beach never feels as crowded as Waikiki.
Lanikai Beach
A narrow ribbon of white sand tucked behind a quiet residential street, Lanikai feels like a secret even though it's no secret at all. The shallow, glassy water goes every shade of blue-green imaginable, and the twin Mokulua Islands sit just offshore as a perfect visual anchor. There are no facilities here — just sand, sea, and a remarkably low-key vibe for such a gorgeous spot.