Long before the towers and tourist shops crowded every block, Waikiki was a quieter place — still glamorous, still sun-soaked, but with wide stretches of open land and a pace that felt distinctly unhurried. The name itself means “spouting waters” in Hawaiian, and the area had once been a retreat for Hawaiian royalty before it opened to the wider world. By the time the 1940s arrived, Waikiki was already drawing visitors from the mainland and beyond, anchored by Kalakaua Avenue — the main drag running parallel to the beach — and framed by Diamond Head to the east and the Ala Wai Canal to the north.
This aerial view reveals just how much open, undeveloped land still existed on the mauka (inland) side of Kalakaua Avenue compared to the makai (ocean) side. Platted lots visible in the upper right quadrant signal that the transformation was already underway — homebuilders and businesses were ready to fill in the gaps quickly.
The street-level view of Kalakaua Avenue in those years showed a mix of low-rise buildings, open-air shops, and the occasional grand structure. Trolley buses operated by the Honolulu Rapid Transit system ran the route, and the sidewalks carried both civilians and, increasingly as the war years arrived, men in uniform.
At the heart of Waikiki stood the Moana Hotel, built in 1901 and still the neighborhood’s most iconic landmark. It was Oahu’s first hotel, and its white colonnaded facade gave Kalakaua Avenue a sense of permanence and elegance that newer buildings couldn’t replicate. In 1918, reinforced concrete wings were added to both ends of the original structure, expanding its footprint without diminishing its stately appearance.
Across Kalakaua Avenue from the Moana sat a collection of cottages and bungalows that formed what was known as Moana Court. These low-slung structures created a quiet residential counterpoint to the grand hotel just steps away. Guests at the cottages looked out across the avenue at the Moana’s porte-cochère, while hotel guests looked back at the shaded bungalow gardens.
This was once the view from the Moana Hotel porte-cochère looking across Kalakaua Avenue at the Moana Court bungalows. Moana Court came down in the early 1950s to be replaced by the 1955 Princess Kaiulani Hotel.
Nearby businesses on Kalakaua Avenue reflected the neighborhood’s mix of leisure and commerce. The Earl Thacker Co. operated directly across from the Moana, part of a block that also included small shops, a drugstore, and the Liberty House department store — one of the avenue’s most recognizable retail anchors during the wartime years.
From the upper floors of the Moana Hotel, the full length of Kalakaua Avenue came into view — the rooftop of the 1941 Outrigger Arcade directly below, and further down the block, the distinctive facade of the 1936 Waikiki Theater. That theater, and the commercial block surrounding it, defined the entertainment district of wartime Waikiki.
A few blocks off the main avenue, Waikiki’s side streets told a different story — one of everyday life still ticking along. On Kalaimoku Street, a driver could stop to get the car lubed while catching a movie at one of the neighborhood’s Art Deco theaters. The 1941 Kuhio Theater on Kuhio Avenue brought a second movie house to the area, giving residents and servicemen alike another escape.
The crown jewel of Waikiki’s entertainment block was the Waikiki Theater on Kalakaua Avenue. Opened in 1936, it was a pure Art Deco statement — bold lines, vertical signage, and a tropical interior that set it apart from anything on the mainland. The theater sat on the mauka (inland) side of Kalakaua Avenue, directly across from the Royal Hawaiian Hotel, and became one of the most photographed buildings in the neighborhood throughout the 1940s.
During the war years, the Waikiki Theater drew heavy crowds of uniformed servicemen. With tourism shut down following the attack on Pearl Harbor in December 1941, Waikiki pivoted entirely into a rest and recreation zone for the U.S. military. Soldiers and sailors filled the streets, the beaches, and every venue willing to host them — including the Waikiki Theater, which remained open throughout the war.
It was closed in 2002, and demolished in 2005.
By 1948, the theater was showing Hollywood releases like “Adventures of Don Juan” starring Errol Flynn and Viveca Lindfors. The glowing marquee at night turned that stretch of Kalakaua Avenue into something genuinely cinematic.
Away from the main avenue, Waikiki had quieter pockets that felt more like a village than a resort district. The Willard Inn on Lewers Road at Kalia offered European-style cottage accommodations surrounded by tropical gardens. It was a low-key, low-rise property — a world away from the Moana’s grandeur — with a rattan-furnished lanai lounge where guests relaxed and individual lanai guest rooms that opened onto the greenery.
This low rise cottage hotel became the site of the architect/hotelier Roy Kelley’s seven floor 1950-2005 Edgewater Hotel.
Street life in 1940s Waikiki had its own rhythm. Lei stringers worked the park on the makai side of Kalakaua Avenue near Beachwalk. Picturesque wooden cottages still stood on residential corners just a block from the beach — like the one at the northwest corner of Liliuokalani and Koa Avenues, near Kuhio Beach. Lewers Street between Kuhio Avenue and the Ala Wai Boulevard retained a genuinely residential character, with homes and small apartment buildings lining the sidewalks.
Picturesque cottage on the NW corner of Waikiki’s Liliuokalani and Koa Avenues, just a block mauka from Kuhio Beach. The 1970 19-story Waikiki Resort Hotel is on the site today.
Hotelier Roy Kelley made his mark on Waikiki during this period with a string of modest but well-designed properties. His first hotel, the five-story Islander at 351 Seaside Avenue just makai of Kuhio Avenue, opened in the 1940s with tropical decor and penthouse views stretching toward Diamond Head. Kelley’s approach — practical, well-located, affordable — made his properties popular with the servicemen and postwar visitors that Waikiki was beginning to welcome back.
Other Kalakaua Avenue landmarks filled out the neighborhood’s personality. The Waikiki Tavern and Inn sat on the makai side of the avenue in the 1930s and into the early 1940s. St. Augustine’s Catholic Church occupied the northwest corner of Kalakaua and Ohua Avenues. The Waikiki Elks Club offered its members a billiards lounge and a formal main entrance. The Waikiki Aquarium drew visitors to the eastern end of the avenue near Kapiolani Park. And at the edge of the park, the Waikiki Natatorium — a seawater swimming venue built as a World War I memorial — still had a pair of 7-inch naval cannons mounted on the Kalakaua Avenue side of the structure.
The Ala Wai Canal formed Waikiki’s northern boundary, separating the resort district from the rest of Honolulu. Looking mauka from the canal’s edge in 1947, the view stretched toward Manoa Valley — a reminder that Waikiki was, geographically, a narrow strip of land sandwiched between mountains and sea. The canal itself had been completed in the 1920s as a drainage project, and by the 1940s it was simply part of the landscape.
The beach itself remained the center of everything. The Outrigger Canoe Club operated along the waterfront, and beachside restaurants served meals at open-air patio tables while waiters worked the tables just steps from the sand. The Moana Hotel’s beachfront setup drew officers and guests, while the wider stretch of Waikiki Beach stayed accessible to servicemen, locals, and the occasional civilian tourist.
From 1941 through 1945, with civilian tourism halted by the war, Waikiki operated primarily as a military recreation zone. The Moana Hotel served as a formal rest and respite facility for soldiers throughout this period. Sailors walked the beach in uniform. The Moana Hotel served as a formal rest and respite facility for soldiers, and military ships filled the waters near Pearl Harbor just a short distance to the west. When the war ended, celebrations broke out on the same streets where servicemen had spent years waiting.
Waikiki Beach itself required constant maintenance even in this era. Chronic erosion wore away more than a foot of shoreline each year, and restoration efforts brought in sand by boat and barge from Southern California — a practice that dated back to the 1920s and continued through the postwar decades at a cost of $2.4 million per cycle. The beach that looked so effortlessly natural was, in fact, actively maintained to stay that way.
