It’s almost impossible to picture today’s glittering Waikīkī as anything but a sun-drenched playground of surfers, luxury resorts and beachfront cocktails. Yet rewind to the late 1800s and you’d find a very different landscape – swampy lowlands, taro patches and duck ponds stretching toward a quiet shoreline once reserved for Hawaiian royalty and wealthy kama‘āina (locals).
The transformation from rural backwater to global icon didn’t happen overnight. Early foreign visitors began arriving in the 1830s and by the 1860s a road connected Honolulu to Waikīkī, opening the door to tourism. One of the first to recognise the area’s potential was English businessman Walter Peacock, who built the neighbourhood’s first true beachfront hotel in 1901 – complete with a grand porte-cochère and wide ocean-facing verandahs. He named it “Moana,” the Hawaiian word for ocean, and back then guests would gather at a pier-side pavilion to listen to Hawaiian music drifting over the waves.
Moana Surfrider
That spirit of old Hawai‘i still lingers today at the Moana Surfrider, a Westin Resort & Spa. Affectionately known as the “First Lady of Waikīkī”, the grand Victorian landmark remains one of the most evocative places to stay on O‘ahu. Step into its breezy lobby and you’re immediately transported to a more graceful era – refined, but never stuffy.
At the heart of the Moana’s courtyard stands its most beloved resident: a towering banyan tree planted in 1904. Once just a sapling, it now stretches more than 20 metres high and casts a canopy across the courtyard, where guests gather at The Beach Bar for cocktails and live music and The Veranda for oceanfront dining and afternoon tea.
That balance between past and present is woven throughout the property. Recent updates to the historic lobby preserve its colonial-style architecture while introducing contemporary touches. Rooms in the original Banyan Wing have also been updated, with a nod to traditional Hawaiian elements like limu (seaweed), once abundant along the shoreline, through subtle textures and design details.
But what truly sets the Moana apart is how it actively brings its history to life. Guests can join complimentary guided historical tours (held Mondays and Wednesdays), where storytellers recount tales of early visitors, architectural milestones and curious anecdotes.
The Royal Hawaiian
A short stroll along the beach brings you to another icon, The Royal Hawaiian, a Luxury Collection Resort. Instantly recognisable by its blush-pink façade, the “Pink Palace of the Pacific” has been synonymous with glamour since its grand opening in 1927.
The site itself carries historical resonance. It was once home to Hawaiian royalty, including King Kamehameha I, and later housed the summer palace of Queen Ka‘ahumanu. When The Royal Hawaiian opened, it marked a bold new chapter in luxury travel – built in just 18 months at a cost of $4 million, an extraordinary sum at the time.
Designed in a romantic Spanish-Moorish style inspired by Hollywood star Rudolph Valentino, the resort quickly became the social epicentre of Waikīkī. Its opening night gala drew more than 1,200 guests in black tie, with music from the Honolulu Symphony Orchestra. The Honolulu Star-Bulletin called it “the first resort hostelry in America.”
Today, The Royal Hawaiian continues to honour that legacy while inviting guests to explore it firsthand. Weekly historical tours (held Tuesdays, Thursdays and Fridays) offer a look into the hotel’s past – from its glamorous heyday to its wartime chapter, when it was repurposed as a Navy rest and recreation centre following the attack on Pearl Harbor in 1941.
The recently opened Royal Hawaiian Historic Gallery showcases archival photographs, vintage fashion and artefacts from the original opening night bring the past vividly into focus.
Waikīkī Circle Hotel
While the Moana Surfrider and Royal Hawaiian represent Waikīkī’s early elegance, the 1960s ushered in a new era of modern tourism, and with it, a different kind of hotel experience. Enter the Waikīkī Circle Hotel.
Opened in 1963, the hotel stands out immediately thanks to its distinctive cylindrical design, often compared to a Chinese lantern. It was developed by Emma Kwock Chun, a trailblazing entrepreneur who immigrated from China at just 16 and became the first Asian-born woman to own and develop a hotel in Waikīkī.
At a time when high-rise towers were rapidly reshaping the coastline, the Waikīkī Circle Hotel offered something more intimate. Its 14-storey structure was designed to maximise ocean views, with private lanais (balconies) that capture Waikīkī’s ever-changing light. Decades later, it remains a family-owned Waikīkī hotel – a rarity in a district dominated by global brands.
Together, these hotels tell the story of Waikīkī’s evolution – from royal retreat to Victorian seaside escape, from roaring ’20s glamour to mid-century modern reinvention and beyond.
