Things to Do in Kailua
63 tours & activities · 8 attractions
Tours & Activities
View all →Popoia Island & Kailua Bay Guided Kayak Tour
Twin Islands Guided Kayak Tour
Popoia Island Kayak and E-Bike Guided Adventure Tour
2-Hour Guided Kayak + Beach Time
Popoia Island & Kailua Bay Guided Kayak Tour- Full Day
Popoia Island Kayak and E-Bike Guided Adventure Tour- Full Day
Rainforest Self-Guided Kayak Tour
Guided Mokulua Islands Kayak Tour and E-Bike Adventure
Mokulua Islands Guided Kayak Tour, Kailua's Twin Islands
Kailua E-Bike Kau Kau Adventure - Guided Scenic and Food Tour - Full Day
Kailua E-bike Kau Kau Adventure - Guided Scenic and Food Tour - Half Day
East Oahu Self-Guided Kayak Experience
Attractions in Kailua
Pillbox Trail (Lanikai)
Climb to WWII military bunkers overlooking turquoise Lanikai and Kailua beaches on this moderate 1.5-mile trail. The rewarding 600-foot ascent through scrubland leads to panoramic ocean views and perfect photo spots at historic concrete pillboxes.
Maunawili Demonstration Trail
Escape the crowds on this rewarding 2.5-mile ridge hike through native Hawaiian forest. The Maunawili Demonstration Trail offers panoramic views of Kailua Bay and the Mokulua Islands without permits or fees, though muddy conditions require sturdy boots.
Kailua Beach Park
Kailua Beach Park boasts world-renowned powdery white sand and brilliant turquoise waters on Oahu's windward coast. Protected by offshore islands, the calm waters are perfect for swimming, snorkeling, and paddleboarding away from Waikiki crowds.
Olomana Trail (Three Peaks)
A technical ridge hike ascending three challenging peaks above Kailua's windward coast. The demanding trail features rope-assisted climbs and knife-edge ridges, with most hikers safely turning back after reaching the rewarding first summit at 1,643 feet.
Lanikai Beach
Lanikai Beach offers half a mile of powdery white sand and turquoise waters on Oahu's windward coast. Consistently ranked among the world's best beaches, this hidden gem features calm swimming conditions and stunning views of the offshore Mokulua Islands.
Bellows Beach
A military recreation beach on Oahu's windward coast offering calmer waves and fewer crowds than nearby Kailua Beach. Open weekends and holidays only, with ID checkpoint access and a 400-person daily limit creating an uncrowded family-friendly experience.
Kaiwa Ridge (Lanikai Pillbox)
Historic WWII bunkers turned Instagram-famous viewpoints overlooking Lanikai Beach's turquoise waters and twin Mokulua Islands. This moderate 1.8-mile hike offers Oahu's most photographed ocean panoramas from concrete pillboxes perched on Kaiwa Ridge.
Maunawili Falls
Maunawili Falls offers a rewarding 20-foot waterfall and swimming hole after a challenging 3-mile muddy hike through Oahu's rainforest. The moderate trail takes 2-3 hours round-trip with stream crossings and steep, slippery terrain requiring sturdy hiking boots.
About Kailua
Kailua sits on Oahu's windward coast, 30 minutes from Waikiki when traffic cooperates. This beach town draws visitors primarily for its powder-soft white sand beaches and turquoise waters that rank among Hawaii's most photographed coastlines.
Kailua Beach Park anchors the area with facilities and easy access, while nearby Lanikai Beach offers a more secluded stretch of sand accessible through residential neighborhoods. Both beaches provide ideal conditions for kayaking, stand-up paddleboarding, and swimming in calm, protected waters.
The town supports a thriving activity scene beyond beach time. Food tours highlight local favorites and cultural spots often missed by casual visitors. Surf shops rent boards suited to the area's consistent but gentle waves. The famous Pillbox Trail starts just above Lanikai, offering panoramic views of the coast and offshore islands after a moderate 20-minute hike.
Plan for morning traffic delays from Honolulu, especially on weekends when locals head to these same beaches. Parking fills up quickly near popular beach access points. Most visitors spend a full day here, combining beach time with hiking or water activities. The compact town center provides dining options and gear rentals within walking distance of the main beaches.