Oʻahu

Choose Oahu for a first trip that mixes beach days with city life and history. Honolulu is a real city, and around Waikiki you can manage with public transit, Biki bikeshare or the Waikiki Trolley, so a rental car is optional for part of the stay. Pearl Harbor and Iolani Palace cover the history, and winter brings big surf to the North Shore if you want to watch it from the sand. The trade-off is pace. Expect crowds and city traffic, and book ahead for Diamond Head, which needs entry and parking reservations for non-residents. Oahu works well as the first half of a two-island trip, with a quieter neighbor island to finish.