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Oahu Itineraries

Town: Long Weekend

Settle into your Waikiki hotel and don't rush to do anything but relax at the beach. Appreciate the sun, the scenery, and the spirit of island living—that is, "No worry, beef curry!" Ocean enthusiasts can snorkel at Hanauma Bay or surf at Waikiki Beach, kids will enjoy the Honolulu Zoo and the Waikiki Aquarium, and couples can marvel at the sunsets with a mai tai in one hand and their honey's hand in the other.

Town: One Week

Besides beach time, add a dose of culture and history. Visit the Bishop Museum, tour the Iolani Palace, and pay homage to the fallen at Pearl Harbor. For closer encounters with Oahu's natural beauty, hike through a lush forest to Manoa Falls or up to the top of Diamond Head Crater for spectacular views of Waikiki. For nightlife and dining options outside Waikiki, visit the bustling Chinatown district.

Town: Two Weeks

Since you're practically a kamaaina (an island local), you should visit some local hotspots. Catch an indie film at the Doris Duke Theatre, view the latest exhibition at Mark’s Garage, and check out popular bands at Anna Banana’s. Graduate to longer hikes like the Kuliouou Trail and spend a few days doing activities in the “country.” Before you head home, pick up souvenirs at the Aloha Stadium swap meet.

Country: Long Weekend

The beaches along rural Oahu invite peaceful contemplation, so take enough time to soak up the country feeling. If it's summer, go for a dip in Waimea Bay. If it's winter, chances are the surfers are putting on a show at Pipeline. After a sun-drenched day, buy a six-pack at Foodland and barbecue on the grill.

Country: One Week

Advance your waterman skills by kayaking the Anahulu Stream or exploring the underwater caves at Shark's Cove. If you need to give your swimsuits a day to dry, head to the hills. There are numerous rewarding hikes in the verdant Koolau Mountains, and a one-mile, zero-elevation walk will take you through a world-class botanical garden to Waimea Falls. At night, hang out with locals at Haleiwa Joe’s or Kainoa’s Sports Bar.

Country: Two Weeks

Take a drive along the Windward Coast all the way down to Waimanalo. Appreciate the dramatic change of scenery with a horseback ride at Kualoa Ranch or a kite-surfing lesson in Kailua. Visit the surf museum, shop at the boutiques, and sample the lunchwagons in Haleiwa. If it's raining in the country, a good option is to embark on some adventures in town, where it may be perfectly sunny. 

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