KAILUA 290 Hawaii Military Guide • Summer-Fall 2026 reports or ask a lifeguard since stings are known to shock the system. Kailua is also known for its selection of topnotch surf shops. Among the local favorites are Gnarwall Surf Shop, HIC Hawaiian Island Creations Kailua, and Hawaiian Watersports. Also calling Kailua home is Windward Boats, one of the island’s top kayak and water vessel suppliers. KAYAK OR SUP TO THE MOKES The small islands offshore of Kailua Beach Park are designated bird sanctuaries and called Popoia, Moku Nui and Moku Iku. The latter two are collectively called “The Mokes” by locals. On a calm day, Moku Nui awaits just a short kayak paddle away with sea turtles, coral reefs and vibrant fish often surrounding its edges. If you’re lucky, you might spot humpback whales typically between December and April. Want to explore the Mokes via a water adventure or experience Kailua Beach? Kailua Beach Adventures is your go-to source. The outfitter teaches beginning and refresher courses for kayaking and stand up paddle (SUP). Within walking distance of Kailua Beach Park, the shop also provides rentals for boogie boards, surfboards and snorkeling gear. HIT THE TRAILS Kailua is home to some of Oahu’s most popular trails for both beginners and extremely advanced hikers. Lanikai Pillboxes Hike is a popular trek with a steep, sometimes slippery start that rewards with spectacular views of Kailua Bay. The trail is named after the World War II bunkers or pillboxes scattered atop the mountain. Olomana Hike has earned a reputation as one of the most difficult on Oahu. A full-day trek for advanced hikers who are not afraid of heights, Olomana challenges as a narrow ridge trail transgressing three high peaks. Rent a kayak for a fun day on the bay.
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