From Waikiki, you can get to Kailua, one of Oahu’s priciest zip codes, by driving north over the Pali Highway or going the “long way” east around Makapuu Point. Either way, this lush windward Oahu town is well worth the scenic 40-to-75-minute drive.
Tree-lined streets bordered by an eclectic assortment of shops provide a pleasant, walkable experience. Don’t miss Island Treasures, which showcases the creations of more than 800 local artists and craftsmen. Bookends is packed from floor to ceiling with new, used and out-of-print titles. Kailua is also known for its antique stores—Alii Antiques, Hunter Collectibles, Antiques & Treasures, and Heritage Antiques & Gifts.
Two wonderful farmers’ markets attract crowds on Thursdays from 5 to 7:30 p.m. and Sundays from 8:30 a.m. to noon. Come Christmas, you might catch a glimpse of President Obama and his entourage at Island Snow. He always orders what’s been dubbed the “Snowbama”—shave ice with cherry, melon, lemon-lime, and passion-guava syrups. Reserve time to check out Kailua Beach, a mecca for windsurfers, kitesurfers, and stand-up paddleboard enthusiasts.