For the complete town and country experience on Oahu, grab a rental and make tracks for Haleiwa, the North Shore gateway. Getting there is half the fun, because you have two wildly distinct choices. I opted to meander back to Honolulu Airport, at the end of my trip, along the lush Windward Coast, through sleepy hamlets with roadside stands selling succulent mangoes, bright tropical pareu, fresh corn, and pond-raised prawns.
The route offers the most arresting vistas of those emerald-hued volcanic ranges, with their strikingly corrugated folds of Jurassic Park fame. Huddled at its base is the famed movie-set location of Kualoa Ranch. But when you’re first heading to the North Shore, take the Central Oahu route via H2. The red-earthed heart of the island is a broad and fertile valley, where pineapple and sugar-canes march their way to the Waianae Mountains.
An hour out of Honolulu and just past Wahiawa, the route becomes the Kamehameha Highway (H99) which is where I made my first stop. How could you possibly pass the Dole Pineapple Plantation and the delectable temptation of devouring a scoop or two of Dole Whip? This pineapple-infused soft-serve delight is just the first of many signature tastes that radiantly embodies the sensory allure of North Oahu. I dropped by early morning, sans the crowds, downing my Dole Whip while gazing at the Pineapple Express locomotive, which heartily blew its whistle to herald the start of the new day’s service. It’s just 10 minutes drive from Dole Plantation to Haleiwa, Hawaii's surf city. This quaint and rustic sugar-plantation town now enjoys historic protection.
Its ensemble of faded clapboard stores, strung around a picturesque harbour, sets the stage for the surfie crowd, who flock here from all over the planet. Haleiwa is their holy-grail, a surf mecca, groaning with raffishly charming roadside surfie stores, boutique galleries and eateries. But the most compelling mercantile landmark would have to be Surf N Sea, where its vintage architecture pays homage to its legacy. Originally, the century-old beachfront building was a train station with accommodation upstairs. The Haleiwa Hotel was Hawaii’s first destination resort, before morphing into a general store after World War II.
Since 1965, it’s been home to Surf N Sea, Hawaii’s oldest surf and dive shop. Joe Green has been the ebullient owner for the past 35 years and warmly welcomed me into his part-shop, part-ocean sports shrine, brimming with over 300 surfboards and every imaginable surf brand. Feasting my eyes on all of the surf memorabilia, it’s no wonder many surfies consider this place museum-worthy. The rustic ceilings and walls hold Green's personal collection of vintage surfboards, including the Duke's final fibreglass board from 1968. Joe is also a master ukulele-maker, all handmade from 100% recycled wood, including mango, koa and opuma. Joe salvaged and reshaped ipe wood from the building’s floors, which he has repurposed into the fret board bridges adorning all of his ukuleles.
Impeccably designed, they’re an incomparable buy – an authentic slice of Haleiwa to take home. Joe patiently tried to teach me how to play the ukulele – with mixed results. More iconic North Shore tastes were calling, and just down the road from Surf N Sea is Matsumoto Shave Ice’s original store in Haleiwa. Established in 1951, the pioneers of Hawaiian snow cones were doing a roaring trade when I lined up for my rainbow-striped offering of sweet syrup infused shave ice. Then there’s Ted’s Bakery, another North Shore legend, where you’ll swoon over their insatiable chocolate haupia pie. It is chocolaty, coconutty and encrusted with macadamias. What a knock-out!
And you’ll want to stake out the hole in the wall bakery in the middle of a field, just west of Haleiwa. Paalaa Kai bakery is a 40 year old institution beloved for its freshly-made snow puffies, flaky and buttery pastries, stuffed with cold, creamy custard...