All the Hawaiian Islands have different personalities. Oahu itself differes hugely from the North Shore, to Windward, to metro Honolulu. And then there's notorious Waikiki Beach, viewed often as a sort of schlocky Vegas of the Pacific, but in many ways this tourist trap is the heart of the real Hawaii. Start with the iconic view: Diamond Head is on display everywhere, a sight as recognizable as the Golden Gate Bridge, Eiffel Tower and other world landmarks.
Waikiki is the best place in Hawaii if you want to just chill in the tropical sunshine and relax—and still be in the center of activity. Vacationing in Waikiki is an economy move as well, since you don't really need a rental car and a connecting flight to an outer island is not necessary. You can also score a deal on room prices (though you want to avoid landing at a dive).
On the north end of Waikiki, past the Ala Wai Harbor, is Ala Moana Park. Locals gather to frolic at this huge greenspace, with playfields, jogging paths, and a protected swimming area. And, oh yeah, just across the street is the Disneyesque Ala Moana Shopping Center. You can reach all this on foot or via a trolley that runs from Waikiki.
Yes, lounges bearing pale flesh is a common sight. But WKK is rich with history, since these former swamplands were home to Hawaiian ali'i (royalty). A heritage path with interpretive signs is right there. The Army Museum along the way is a memorable freebie.
Duke Kahanmoku Lagoon rests near the Hilton on the north end of the strip, where a fireworks show lights the sky after sunset has dimmed.
The Royal Hawaiin Hotel, a.k.a. the Pink Lady, still conjurs the image of the glory days of post-war, Matson cruise ship tourism—even though the hotel is now hemmed in by modern buildings.
Kissing cousin to the Pink Lady is the Moana Surfrider, the first hotel on Waikiki Beach, built in 1901.
No doubt kitschy trinkets are plentiful along the main drag of Kalakaua Boulevard. But most visitors will be surprised to see all the big names in designer fashion, along with fine art galleries walking along Luxury Row: Bottega Veneta, Chanel, Coach, Gucci, Hugo Boss, Tiffany, Tod’s and Yves Saint Laurent.
With nearly a million people, Oahu can be intimidating. Pick up a copy of Oahu Trailblazer before your visit to make things easy. It has all the main attractions, as well as hidden sights, from Honolulu and Waikiki to the rural beaches of the North Shore.