Things to Do in Kailua
The local family guide to Kailua, Oʻahu, from the Windward Weekly team: the beaches worth your morning, the hike everyone asks about, the markets, the keiki favorites, and where to eat after. For what's on this week, see This Weekend and the latest issue.
The Beaches
Kailua's whole coastline is one long crescent of soft sand and calm, reef-sheltered water. Pick your park by mood.
Kailua Beach Park
The family default: two and a half miles of sand, lifeguards, showers, shade trees and a big parking lot. The bay is gentle enough for first-time paddlers and swimmers, and the park lawns host half of Kailua's birthday parties.
Lanikai Beach
The postcard: powder sand and glassy water facing the Mokulua Islands, famous for sunrise. No lifeguard, no facilities and street parking only, so go early, keep voices down and pack out everything. The neighborhood thanks you.
Kalama Beach Park
The quiet local park at the south end of the bay. Grass, shade, a small shorebreak for boogie boards and room to spread out when the main beach park is packed.
On the Water
Kayak to the Mokulua Islands
The classic Kailua morning: paddle out to Moku Nui, a state bird sanctuary with a small landing beach, and look back at the Koʻolau range. Rentals and guided tours launch from Kailua Beach, and kamaʻāina save 25% on rentals at Kailua Beach Adventures, see the Deals page. The full playbook, route, permit and all, is in our Field Guide to kayaking the Mokes.
Paddle the Bay
Stand-up paddleboards, outrigger canoes and wing foils all share Kailua Bay. Mornings are calmest before the trade winds fill in around midday.
The Hikes
Lanikai Pillbox (Kaiwa Ridge)
Short, steep and worth it: two WWII-era pillboxes above Lanikai with the best sunrise view on the windward side. Trailhead is on Kaʻelepulu Drive in Lanikai. Go at dawn for the view and the parking, and stay on the trail.
Olomana (Three Peaks)
The dramatic ridge you can see from all over Kailua. Be clear-eyed: this one is for experienced hikers only, with ropes, exposure and real consequences. It is not a keiki hike.
With Keiki
Sea Life Park, Waimānalo
Dolphins, sea lions, turtles and a seabird sanctuary, ten minutes from Kailua. Kamaʻāina admission is 55% off, see Deals.
Kailua Library
Storytimes, the children's room and a steady run of free programs. This week's schedule is always in the latest issue.
Kailua Cinemas
The neighborhood theater, with $7 Tuesdays. Showtimes and the week's movies are in every issue.
Waimānalo Country Farms
Sunflower fields in season, pumpkin patch days in fall, and farm stands year round, under the Koʻolau cliffs in Waimānalo.
Farmers Markets
Four weekly markets within fifteen minutes, including two on Sunday mornings. Days, times and parking tips are in our farmers market guide.
Eat & Drink
Kailua Town
Maui Brewing's Kailua outpost runs a weekday happy hour, Big City Diner does kids-eat-free Thursdays, and the town's small restaurants punch well above their size. Current offers are collected on the Deals page.
Thursday Night Market Dinner
The Thursday evening farmers market at Kailua Town Center doubles as the town's pau-hana dinner run: ready-to-eat vendors, live music and picnic tables. Details in the market guide.
Worth the Short Drive
Hoʻomaluhia Botanical Garden, Kāneʻohe
400 acres of garden under the Koʻolau cliffs, free entry, and the most peaceful picnic lawns on the island. Go after rain for the full waterfall backdrop.
Waimea Valley, North Shore
A cultural valley, botanical gardens and a swimmable waterfall. Kamaʻāina admission is $10, see Deals.
Bishop Museum & Honolulu Zoo
The two big Honolulu family days out, both with kamaʻāina rates well under the visitor price. Rates and terms are on the Deals page.
Never miss a windward weekend
Windward Weekly is the free email that rounds up everything happening in Kailua, Kāneʻohe and Waimānalo, every week, presented by My Kailua.
Subscribe Free This Weekend Live MusicA Windward Weekly guide · presented by My Kailua · Deals and market details checked November 14, 2026