Things to Do in Kailua
Kailua's attractions run toward the outdoors and the genuinely local -- a nationally ranked beach, a well-known ridge hike, offshore island kayaking, and a real cultural and ecological wetland site -- rather than a manufactured tourist-attraction strip. This page covers what's actually here, sourced.
Kailua Beach Park: The Main Event, and It Earns It
Kailua Beach Park is the town's central attraction and a genuinely, repeatedly ranked one: Stephen Leatherman ('Dr. Beach') named it the best beach in America in 1998 and again in 2019, citing its white sand, small and generally gentle waves, and well-managed public facilities including picnic tables, restrooms, and showers. Hawaii placed four beaches in his 2025 top ten overall. The park offers a genuinely wide, sandy, swimmable beach protected by an offshore reef, making it reliably calm and family-friendly across nearly all conditions -- a real, sourced distinction from more surf-exposed Hawaii beaches.
The Lanikai Pillbox Hike (Kaiwa Ridge Trail)
The Lanikai Pillbox Trail, also called the Kaiwa Ridge Trail, is one of Oahu's most popular short hikes, typically taking 30-45 minutes round trip and accessible to hikers of a range of skill levels, though it does climb a genuinely steep ridge. At the top sit two World War II-era concrete pillbox bunkers, offering panoramic views back over Lanikai, Kailua Bay, and the Mokulua Islands. The trail's popularity brings real visitor foot traffic and parking pressure to the residential Lanikai streets it starts from -- a genuine local tradeoff worth knowing, whether you're a visitor trying to park considerately or a resident weighing what living near a well-known trailhead actually involves.
Kayaking to the Mokulua Islands and Popoia (Flat) Island
The Mokulua Islands ('the Mokes'), visible offshore from Kailua and Lanikai beaches, are a roughly 30-minute kayak, stand-up paddle, or outrigger canoe trip from shore. Moku Nui, the larger island, is open to visitors and popular for its small beach and snorkeling; Moku Iki, the smaller of the two, is off-limits. Closer to shore, Popoia Island (Flat Island), about a quarter-mile off Kailua Beach Park, is a state seabird sanctuary reachable by a short paddle or swim, with tide pools and views back toward the Mokulua Islands and Oahu's mountains -- and home to thousands of nesting seabirds, including wedge-tailed shearwaters and Bulwer's petrels. Kailua Beach Adventures and other outfitters on Kailua Road rent kayaks for both destinations.
Kawainui Marsh and Ulupō Heiau
Kawainui Marsh, Hawaii's largest remaining wetland at roughly 830 acres, offers a genuinely different kind of Kailua experience -- a Ramsar-recognized wetland (designated 2005) supporting four endangered native Hawaiian waterbird species, with birding and walking access along its edges. Overlooking the marsh sits Ulupō Heiau, an ancient stone platform roughly 180 feet long and up to 30 feet high, associated in Hawaiian oral tradition with the menehune and later with O'ahu's high chiefs -- a real, accessible piece of pre-contact Hawaiian history within the town itself, not a recreated or commercial cultural attraction.
Water Sports on Kailua Bay
Beyond swimming and kayaking, Kailua Bay's steady trade winds make it one of the best-known windsurfing and kiteboarding locations in the world, with a documented history dating to the sport's earliest days in the 1970s. Multiple outfitters offer lessons and rentals directly from Kailua Beach, making this a genuinely accessible activity for a beginner, not just a spot for experienced wind-sports athletes. See this site's Boating & Water Access and Seasonal Recreation pages for more on both the wind patterns and the broader on-the-water activity scene.
Marine Corps Base Hawaii and Its Adjacent Public Access
While Marine Corps Base Hawaii itself is an active military installation and not generally open to the public, its presence on the nearby Mokapu Peninsula is part of the physical and historical backdrop of the Kailuana Place area where the Obama family vacationed, and the base periodically hosts public events and air shows that draw visitors from around the island -- though this page does not state a current schedule, since these events and their public-access terms change from year to year. For most visitors, the base is a notable neighbor and a piece of local history rather than a destination itself.
Fishing on the Flats
For visitors and residents interested in fishing rather than swimming or paddling, Kailua Bay's shallow flats support a genuine, specialized bonefish sight-fishing scene, with at least one dedicated local outfitter running guided trips. This is a real, distinct activity from the beach and paddling options above -- more technical, generally guided, and appealing to a different kind of visitor than a family beach day. This site's Fishing page covers the specifics in more depth, including how it differs from the deep-sea charter fishing more associated with other Hawaii markets.
Day Trips Beyond Kailua Itself
Because Kailua sits within a 25-to-40-minute drive of downtown Honolulu and Waikiki via the Pali Highway or H-3 tunnels, it functions well as a home base for day trips to Oahu's broader attractions -- Honolulu's museums and Chinatown, Waikiki's beach and shopping district, or Diamond Head State Monument, all realistically reachable without an overnight stay elsewhere. In the other direction, Kailua sits closer to the Windward and North Shore side of the island than Honolulu does, putting attractions like the Byodo-In Temple in Kaneohe's Valley of the Temples within an easy short drive as well.
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Get a Free Agent Referral →Independent research. No ads. No sponsored listings. Data sourced from: the Honolulu Star-Advertiser and Hawaii Magazine for Dr. Beach's 1998, 2019, and 2025 Kailua Beach rankings and criteria; TheOutbound.com and ActiveOahuTours.com for the Lanikai Pillbox/Kaiwa Ridge Trail's length, difficulty, and history; TheOutbound.com, HelloJetlag.com, and YourFriendTheNomad.com for Mokulua Islands and Popoia (Flat) Island kayaking distances and seabird-sanctuary status; DLNR (dlnr.hawaii.gov) and Wikipedia's "Kawainui Marsh" and "Ulupō Heiau State Historic Site" entries for the marsh's size, 2005 Ramsar designation, and Ulupō Heiau's dimensions and cultural history; and Hawaiian WaterSports (pwhawaii.org) for Kailua Bay's wind-sports history and current outfitter access. Facts not independently confirmed and not invented here include: current park hours, parking availability, or trail-access restrictions, all of which can change and are better confirmed with the City and County of Honolulu Department of Parks and Recreation or DLNR directly before a visit. Nothing on this page is a substitute for checking current conditions and access rules before visiting any specific site.