Sand first
Kailua Beach
Kailua Beach is 2.5 miles of fine white sand and calm, shallow water — consistently ranked among the best beaches in the country. Kailua Beach Park is the main access point along it, with parking, restrooms, showers, picnic tables, and lifeguards. The windward trades make the north end reliably good for kiteboarding and windsurfing. Kalama Beach Park continues the same stretch of sand just to the north, with its own parking; there's one public beach access between the two parks, and three more public accesses further north beyond Kalama.
Lanikai Beach
A short drive or bike ride south of Kailua Beach — narrower, calmer, and postcard-turquoise, with the twin Mokulua Islands sitting just offshore. It has the calmest water of any beach along this stretch. There are no restrooms or showers here. Street parking only, and it fills early; this is the one to get to before 8am — on holiday long weekends, expect no parking to be available at all.
Flagpoles & Castles
The water gets progressively rougher heading north from Kalama Beach Park. Flagpoles is the well-known local bodyboarding and surf spot along here, and Castles, at the north end, turns into a surf break when the east side swell picks up.
Parking at Lanikai: only park on the side of the loop road opposite the bike lane, and make sure your car is pointed in the same direction as traffic is flowing. On the narrow side streets, some visitors park facing the wrong way — that's illegal and it gets ticketed. Never park in front of a driveway, either. Lanikai residents routinely call the police over parking violations, so it's worth taking seriously — and on holiday long weekends, there is typically no legal parking left at all.
Paddle out
Kayak to the Mokulua Islands
Launch from Kailua Beach and paddle roughly a mile out to Moku Nui, the larger of the two Mokulua Islands, for a small beach and good snorkeling. Kailua Beach Adventures (formerly Kailua Sailboards & Kayaks) and Hawaiian Watersports both rent kayaks and run guided tours if you'd rather not navigate the crossing solo, and there are a handful of other outfitters around town renting kayaks too. Inexperienced paddlers may prefer Flat Island (Popoiʻa) instead — it's much closer to shore and a safer, easier paddle than the open-water crossing to the Mokuluas.
Hikes
Kaʻiwa Ridge Trail (the Lanikai Pillboxes)
A steep but short climb to a pair of WWII-era concrete bunkers above Lanikai, with a sweeping view down the coast to the Mokulua Islands. One of Oʻahu's best-known sunrise hikes — go early for both the light and the parking.
Olomana Trail (Mount Olomana)
A steep, long ridge climb behind Maunawili to the first of Olomana's three peaks, with sweeping views over Kailua and the marsh. This is a serious step up from the pillbox hike — narrow, exposed footing and no official maintenance, and there have been hiker deaths on the ridge beyond the first peak. Most people should turn around at the first summit; continuing to the second and third peaks is for experienced, sure-footed hikers only. (Maunawili Falls Trail remains closed for restoration work, with no confirmed reopening date.)
Cool off after: once you're off the sand or down from the ridge, grab a shave ice from Island Snow or an açaí bowl from The Sunrise Shack, both a short walk away in Kailua Town.
The marsh
Kawainui Marsh & Nā Pōhaku o Hauwahine
The largest wetland in Hawaiʻi, with a flat paved path along its edge for walking or biking and reliable birdwatching, including native waterbirds. Nā Pōhaku o Hauwahine, on a rise overlooking the marsh, is a culturally significant site tied to the moʻo (guardian spirit) Hauwahine — a quieter, more reflective stop than the beach crowds.
Kailua Town Farmers Market
Thursday evenings, Kailua Town
Produce, prepared food, crafts, and live music in a genuinely community atmosphere — a good way to have dinner without picking a restaurant.
Visit a heiau
Ulupō Heiau State Historic Site
A large ancient heiau (temple platform) on the rise above Kawainui Marsh, traditionally said to have been built by the Menehune and later tied to Kailua's ruling chiefs. It's a significant and sacred site, not a hiking trail — please stay off the heiau structure itself, keep the visit quiet, and don't disturb any stones or offerings you may see left there.
Rent a bike
The Bike Shop
Right at the entrance to Kailua on Kailua Road — sales, rentals, and repairs, and the shop most locals point visitors to first.
Kailua Bicycle
A rental shop especially popular with Japanese tourists — hand-drawn Japanese-language maps and a phone holder come with every rental.
Getting between spots: most of this is a short bike ride or a 10–20 minute walk from Kailua Town. A car helps for Maunawili and for hauling kayak gear, but isn't necessary for the beaches or the pillbox hike.