Fred Hemming's Ideal Drive Around Oahu


Growing up on an island, a special occasion for us when visitors came over, was driving around the island. Show them the special parts of our home all in one long day. Instead of focusing our our highlights, which mostly revolved around food, I want to introduce you to someone who is much more qualified as a true ambassador of Aloha. Fred Hemmings, Hawaii’s former state senator, an elder statesman of pro surfing and a fifth-generation islander, loves to share the magic of the state with dignitaries, visitors and just about anyone willing to listen. His great great grandmother came over on the fifth voyage of the Portuguese people from Madeira Island in 1883 and his father landed on Oahu in 1922 from New York, so it’s fair to say his local roots go deep. As a public speaker promoting Hawaiian culture, Hemmings is actively involved in conservation efforts in the state. As a senator, he was instrumental in having President George W. Bush create Papahanaumokuakea, making the Hawaiian northwestern archipelago the world’s largest marine reserve. These days Hemmings can be tracked down for private high-end tours of Oahu, third largest of the Hawaiian Islands, which often visit these sites. Bishop Street “I like to start off on Bishop Street, where you can trace the economic history of the state from the Hawaiian feudal agrarian culture to the sugar and pineapple plantations to the Big Five families/businesses,” Hemmings says. The infamous Big Five include C. Brewer, Alexander and Baldwin, Castle and Cooke, Amfac (originally H. Hackfeld and Company) and Theo H. Davies. Other historic locations also have eponymous origins. Bishop Street is named after Charles Reed Bishop, who married Princess Bernice Pauahi, the granddaughter of King Kamehameha I. First a merchant, later a banker, Bishop created what is now First Hawaiian Bank (today headquartered at 999 Bishop Street) — aptly named, as it was the first bank and, for a time, the tallest building in Honolulu. He also created the Bernice Pauahi Bishop Museum, acknowledging his wife’s estate’s legacy creating the Kamehameha Schools to educate the children of Hawaii. “In 1859, Hawaii was said to have the highest literacy rate — I like to remind people that the Hawaiians did much more than fish and surf,” says Hemmings. “They had a sophisticated culture.”

Iolani Palace If there’s time on the tour, Hemmings makes a right onto King Street to drive by the Iolani Palace, the only royal palace in the United States. Just behind it is the state Capitol building, a unique architectural gem built in 1969. This part of the drive ends at the historic Aloha Tower on Honolulu Harbor. Built in 1926 to welcome arriving passenger ships, the 10-story building was the tallest in the state before high-rise hotels came along.

Highway to North Shore Driving toward the North Shore, Hemmings points out landmarks such as Pearl Harbor. “We talk about how Pearl Harbor was the reason for America’s interest in Hawaii. Just imagine that ‘Day of Infamy,’ December 7, 1941, when Japanese warplanes swept down the slopes of Oahu to sleepy Pearl Harbor,” he says. The H2 highway ends at Wheeler air base and, after a traffic stop, continues on a century-old Kamehameha-era two-lane road that winds around the north and windward shores.

Cultural Gem On the way to the North Shore Hemmings stops by the Kukaniloko Stones, one of the most culturally significant places on the island. “For generations this is where the royalty were born,” he says. “Today it is a surprisingly humble location amid eucalyptus trees in the middle of an abandoned pineapple field.” The five-acre historic site, open daily, is at the intersection of Kamehameha Highway and Whitmore Avenue near the old plantation town of Waihawa.

Surfer’s Paradise Also on the way to the North Shore, the former senator drives past Schofield Barracks. He notes what a prominent role the military plays in Hawaii history and the present-day economy. The long road to Haleiwa passes through fallow pineapple and sugar fields. “This vantage point allows me to explain the science of surfing. Most people ride waves but don’t know where they come from,” he says. “I explain that because of our location in the Pacific, these islands and the North Shore in particular have the most renowned surf in the world.”

A drive through Haleiwa town, “the surfing capital,” is a must. The town is also notable because it has gone out of its way to preserve the plantation-era architecture and ambiance — for example, it’s one of the few places in the nation where the McDonald’s restaurant has no golden arches in front. “I like to stop at a few surfing spots like Haleiwa and Pipeline, Sunset and Waimea beach,” Hemmings says. “I point out that in the ancient times what is now known as Sunset Beach (named by a real estate agent) for centuries was known as Paumalu.”

Salute to the Morgan family of Kualoa Ranch On the hill above Waimea Bay is a well-preserved puu mahuku heiau, a place of worship and often human sacrifice. The old road continues around the island and passes aquaponic farms before arriving in Kahuku, one of 42 former sugar plantations in Hawaii. Hemmings likes to show that once the plantations (and jobs) vanished, people in town were forced to try other pursuits —like raising shrimp. Today it’s a boutique industry serving the tourists and worth a stop for lunch. Driving along the coast sprinkled with little towns, you’ll eventually come upon Kualoa Ranch, which includes Kaaawa Valley, made famous as the backdrop for many movies and television shows. This property, owned by the Morgan family, direct descendants of the early missionaries, could have been used for much more profitable endeavors. Instead, “they have gone out of their way to preserve the beautiful and culturally rich land,” says Hemmings.

Famous View En route back to town on Kamehameha Highway, which runs along the foot of the Koolau Range, the last official stop is the Pali Lookout. “Not only is it a stunning view of of the windward coast all the way to Kahuku,” Hemmings says, “including Kaneohe, Kailua and the steep ridgeline of the Koolau mountain range, but it’s also the place where King Kamehameha I’s army claimed dominion of all the islands by pushing the remaining warriors of Oahu off the cliff at Pali, which resulted in the unification of the Hawaiian Kingdom.”

Nuuanu Valley The journey back to Waikiki descends from the cool heights of Nuuanu Valley, where you can find numerous “hidden Hawaii” sites of cultural and historic significance, locations Hemmings loves to point out as another day’s tour comes to an end.

If you would like to book a tour with Fred, email me at