Kailua, HI

Rent a kayak or stand-up paddleboard from Kailua Beach Adventures and explore the bay. Pack a picnic, find a spot under the ironwood trees, and simply soak in the view of the turquoise water and distant Mokulua Islands.

For a moderate hike with a huge payoff, tackle the Kaiwa Ridge Trail at dawn. The historic military bunkers offer a 360-degree vista that is arguably the best photo op on the windward side.

Start your morning like a local at this iconic green-and-white market. Grab a coffee and a famous Kalapawai Deli sandwich to-go, or sit on the patio and watch the town wake up.

Held at the Kailua Town Center parking lot, this vibrant market is a community hub. Stock up on fresh local produce, tropical flowers, artisan foods, and ready-to-eat treats from dozens of vendors.

This sacred site is a massive stone platform temple built centuries ago. It's a quiet, powerful place to learn about Native Hawaiian history and culture, nestled next to the Kawainui Marsh.

Park the car and wander. Explore unique shops like BookEnds for rare finds, Island Snow for shave ice (a favorite of the Obama family), and the many boutiques along Kailua Road and Oneawa Street.

This exclusive, gated-community neighborhood is home to arguably Hawaii's most famous beach. Characterized by luxurious homes, narrow, palm-lined lanes, and direct access to the pristine, powder-white sands of Lanikai Beach.

The strip of homes directly across from Kailua Beach Park represents classic island living. It's a mix of old-school Hawaiian homes and modern renovations, all with the incredible benefit of being steps from the sand and park.

The commercial and social heart of Kailua. This walkable grid of streets centered around Kailua Road is where you'll find most of the town's restaurants, boutiques, banks, and the post office, all buzzing with local life.

A large, established neighborhood built around a private, spring-fed lake (Kaelepulu Pond). It's known for its strong community feel, good schools, and a mix of mid-century and newer homes, popular with families.

Nestled on the slopes of the Ko'olau Mountains, this neighborhood offers stunning panoramic views of the ocean and Kaneohe Bay. It's quieter, more spread out, and provides quick access to hiking trails like the Maunawili Falls trail.