Kailua is Oʻahu's windward destination — the beach draws visitors from Waikiki who make the thirty-minute drive over the Koʻolau mountains for turquoise water and white sand. The town has gentrified steadily over the last two decades, with boutique shops and artisan coffee replacing some of the old plate lunch counters. But the local food is still there, mixed into the strip malls and side streets.
The Plate Lunch Baseline
Kailua has several plate lunch counters that serve the local population — construction workers, teachers, military families from the nearby bases. The format is the same as everywhere: two scoops, mac salad, protein. The drive-through windows near the Kailua Shopping Center are the best lunch options for the under-$12 plate.
Cinnamon's Restaurant — The Local Brunch
Cinnamon's in the Kailua shopping center is the local brunch institution — red velvet pancakes, guava chiffon French toast, and a full breakfast plate that leans Hawaiian. Weekend waits run 45–60 minutes. Weekday mornings are manageable. Worth it if you're starting a windward-side day.
Kalapawai Market — The Deli
Kalapawai Market at the edge of Kailua near the beach is a full-service market and deli — fresh prepared foods, sandwiches, a wine and beer selection, and the nicest setting in Kailua for an outdoor lunch. The deli sandwiches and salads are the move for a beach picnic.
The North Kailua Move — Waiahole
Seven minutes north of Kailua on Kamehameha Highway, Waiahole Poi Factory is the windward-side destination for Hawaiian food. Fresh-pounded poi made on-site, lau lau, kalua pork, and a roadside setting with views of Kaneohe Bay. The most important food stop on the windward side.
Practical Notes
- Drive over the Likelike or H-3 (Kaneohe) — the H-3 has better views
- Go early on weekends — Kailua Beach parking fills by 9am
- Waiahole Poi Factory: open weekdays and Saturday morning, call ahead
- The Kailua strip malls have the best price-to-quality ratio — ignore the cute boutiques