Kailua Oahu

The Windward Oahu town of Kailua—population 36,513—is only a 30-minute drive from the hustle and bustle of downtown Honolulu, but it may as well be a world away. There are Oahu residents who go for years without making the drive over to this part of the island. And to be truthful, Kailua residents are perfectly okay with that. They rather enjoy having a scenic slice of Hawaiian heaven all to themselves.

Kailua Beach

Kailua Beach’s proximity to several small islands makes it an ideal place for adventuring. Closest to the shore is barren Flat Island, and far off to the east are the Mokulua Islands, commonly known as “Moks” or “Twin Islands.” To the west of Kailua Beach is Kalama Beach, a family-friendly beach with mild waves great for teaching kids how to surf and body board. To the east is Kailua’s sister beach, Lanikai Beach, which is another beautiful stretch of sand, although less accessible since it’s nestled between residential housing and parking is limited.

Kailua Town

Located on Oahu’s Windward Coast, the main part of Kailua Town consists of a few blocks of trendy boutiques, popular restaurants and kamaaina (resident) hangouts, like the Thursday evening farmers’ markets.

Start the morning with pancakes smothered with irresistible macadamia nut sauce at Boots and Kimo’s Homestyle Kitchen or “to die for” crepes at Crepes No Ka Oi. If you’re already at the beach, stroll to Kalapawai Market for coffee and lunch. After a day of body boarding, rehydrate with a refreshing smoothie at Lanikai Juice or cool off like the President with shaved ice from Island Snow. And if you’re in the mood for dressing up—in Kailua terms that means something more than a beach cover-up—Formaggio Grill boasts over 50 wines by the glass.