Kailua (Hawaii County), HI

Most people know Kailua on the Big Island as Kailua-Kona, or simply "Kona," which prevents any mix-ups with the Kailua over on Oʻahu. The heart of town stretches along Kailua Bay and Aliʻi Drive, where historic landmarks, open-air restaurants, small boutiques, and shave ice stands line the oceanfront. It has the feel of a laid-back coastal village where people walk everywhere, even if finding street parking can test your patience on sunny afternoons. As you head uphill, or mauka, the roads open up to larger shopping plazas, grocery stores, and essential services along Queen Kaʻahumanu Highway.

Living in Kona means having rich Hawaiian history woven directly into your daily routine. Along the shore, Huliheʻe Palace, a former royal vacation home built from lava rock, hosts Hawaiian music and hula gatherings on its oceanfront lawn. Mokuaikaua Church, the oldest Christian church in the state, stands right across the street. While the shoreline draws plenty of foot traffic for ocean tours and sunset dining, residents head slightly inland for everyday needs. You will find big-box stores, medical clinics, and county offices at the West Hawaiʻi Civic Center just a quick drive up the hill.

Most newcomers quickly learn that having a car is essential, especially when navigating Aliʻi Drive during peak afternoon traffic, although the island's Hele-On bus provides regular connections between town and Keauhou. For recreation and weekend downtime, Old Kona Airport Park on the north end of the village serves as the main gathering spot. The former runway has been turned into a huge oceanside park with a public pool, sports fields, walking trails, and tide pools, making it a favorite place for sunset strolls, youth sports, and family barbecues.