One of the most delightful little villages on Oahu is the surfing town of Hale’iwa. When I say surfing town, I don’t mean the town itself surfs- that would be silly – but the town does revolve around surfing. Once a plantation village where workers lived and bought what they needed to go about their lives, this village transformed into something else entirely when big wave surfing arrived. Today it is filled with boutiques, galleries, great restaurants, shave ice shops like Matsumoto Shave Ice, and plenty of surf shops. In fact, it is the perfect place to spend the day strolling, shopping, eating, and hanging out with friends and family.
Hale’iwa still has much of the slow paced country village feel about it combined with a chilled out surfer vibe which sits on top of a mouth watering culinary destination and an innovative artisanal movement. Hale’iwa epitomizes the Hawaiian ‘country’ scene without being backward or pretentious.
The town sits between the villages of Pupukea to the East an Waialua to the West. Pupukea is little more than a grocery store, a fire station, and some food trucks (which happen to be sitting at the gateway to the world’s best surfing beaches and the amazing snorkeling at Shark’s Cove) and Waialua has died back to mainly farms,the North Shore Soap Factory and old sugar mill complex. Waialua Bay wraps around and comes into Hale’iwa and then turns into rocky shoreline before reaching world famous surfing at Waimea Bay and the sacred temples in Waimea Valley and atop the hills in Pupukea. The small boat harbor in Hale’iwa is where many shark cage dives, dives, and sailing adventures leave from. To the south of Hale’iwa you will find the Dole Plantation and the town of Wahiawa.
The present day location was the site of an ancient Hawaiian fishing village where it was a common destination for the Hawaiian Ali’i (Royalty) to escape the heat of Honolulu or ‘Ewa in the summer months. People have occupied the area for nearly a thousand years. Hale’iwa got it’s first western style building in 1832 but wasn’t founded as a town until 1898 when Benjamin Dillingham, a local businessman who contracted to have the Hawaiian railway built from the sugar and pineapple fields of the North Shore to the shipping port of Honolulu, saw the potential for tourism and built a hotel at the northern terminus. He named the hotel for the nest of the black frigate bird, called the ‘iwa bird in Hawaiian language. Hale is the Hawaiian word for house, so – House of the Frigate Bird.
The hotel is long gone and village residents fight tooth and nail whenever anyone tries to bring a new hotel into the area. The last thing anyone wants is for Hale’iwa to turn into another Waikiki. If you want to stay on the North Shore, you need to either book a room at the expensive Turtle Bay Resort on the Northeast corner of the island or find a vacation rental. There are no other hotel options.
One of my favorite places to take guests and visitors on Oahu is to the world famous North Shore of Oahu. A day up there usually includes visiting the famous surfing beaches like Banzai Pipeline, Sunset Beach, and Waimea Bay – but it also includes stops such as a 
