Three days going well beyond Waikiki — the North Shore at Sunset Beach and Pipeline, Koko Head Crater hike, and Kailua on the windward coast with the best beach in Hawaii that most tourists never find. This is the Oahu itinerary for people who want to see the island rather than just the hotel zone.
East Oahu first. Koko Head Crater before 8am, Hanauma Bay snorkeling afterward. The juxtaposition of volcanic geology and coral reef in a single morning is very Oahu.
Koko Head is the hardest hike on Oahu's tourist circuit — 1,048 railroad tie steps up the face of a volcanic crater that was used as a military railway in WWII. The steps are uneven, some are suspended over gaps, and the final section is near-vertical. The view at the top looks down into Hanauma Bay on one side and across the windward coast on the other. Start before 7am. Bring water. This is not a casual stroll.
The North Shore is the surfing capital of the world from November through March when the swells hit 20–30 feet. The rest of the year it's a quieter, beautiful stretch of coastline with great food and a completely different energy from Waikiki.
The shrimp trucks on Kamehameha Highway between Haleiwa and Kahuku are a North Shore institution. Giovanni's White Shrimp Truck (the original, since 1993) is the most famous — the garlic butter shrimp plate ($16) with two scoops of rice has been served from this truck for 30+ years. Romy's Kahuku Prawns & Shrimp raises its own prawns on-site and has the best broth options. Both are worth eating at.
Sunset Beach is the most famous big-wave surf spot on earth outside of Jaws on Maui — the Vans Triple Crown of Surfing has been held here since 1975. In summer the water is swimmable; in winter it's a wall of blue water moving faster than most people can process. Either way the beach is spectacular. Ehukai Beach Park (Banzai Pipeline) is one mile west — the Pipeline wave is the most photographed surf break in the world and breaks directly in front of the beach.
Kailua on the windward side of the Ko'olau Mountains is the best beach town on Oahu and largely unknown to tourists. Kailua Beach is the finest swimming beach on the island.
Kailua Beach is a 2-mile crescent of powdered white sand with protected water and the Mokulua Islands offshore. The kayak launch to the Mokes (the twin islands) is 2 miles each way and completely doable for beginners — paddle across, explore the offshore sandbar and seabird nesting area, paddle back. Lanikai, the neighborhood just south of Kailua Beach, has the famous pillbox hike (30 minutes up, panoramic windward coast view).
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