Oʻahu is Hawaii’s most dynamic island—a place where lush nature, deep-rooted history, and surf culture meet under a modern Pacific buzz.
At the end of Farrington Highway, where the island gives way to the sea, we stayed at the Opperman Estate: barefoot luxury at its most soulful. Nestled in jungle-green grounds with 242 feet of private oceanfront, it felt remote, a little wild and effortlessly stylish. The estate didn’t try too hard—it didn’t need to. Waves woke us each morning; daily afternoon rains cleared the air for golden hours of sun. Life there moved to the rhythm of the island.
In the village, we dined with the surf crowd—burgers, grilled fish, papaya and barefoot chatter under string lights as the sun dropped behind the waves. Mornings were for surfing, afternoons for hiking or lying still on the sand, salt-drenched and sky-stunned. With no city lights, the night sky felt close enough to touch.
We packed in some of Oʻahu’s classics too: a visit to the legendary Banzai Pipeline on a day of huge swell, my first surfing lesson at Waikīkī under the gaze of Diamond Head, and the hot climb to its summit for sweeping views of Honolulu. Pearl Harbor brought quiet reflection, a sobering counterpoint to the island’s vibrancy.
Oʻahu was a trip of contrasts—raw nature, powerful history, and a string of personal firsts. It left sand in our shoes and stories we still tell.
