A Walk Through Time

Kaanapali’s historical trail turns back the clock

By: Karla Aronson

So many visitors travel to Maui to lie on the white-sand beach of Kaanapali and stroll along its oceanfront resorts, shops and restaurants, it’s hard to imagine that nearly half a millennium ago native Hawaiian fishing villages of thatched-roof homes dotted the shoreline, and rich agriculture fields extended upwards to the forestlands of the West Maui Mountains. Back in the 1500s, the area, then called Kekaa, functioned as the capital of Maui.

Warriors once waged bloody battles across a stream where golfers now count their strokes on the lush greens. The Kaanapali History and Legends Tour aims to bring that to mind for visitors and residents.

Organized by the Kaanapali Beach Resort Association, guides representing the resorts enliven the history of a Hawaiian civilization once ruled by kings and queens, defended by warriors, and sustained by fishermen, farmers and gatherers living in harmony with their environment.

Through the retelling of legends and local histories, the tour focuses on ancient history as well as the plantation and missionary eras and early tourism development. The free, 90-minute tour begins aboard a trolley, making four stops, and continues on foot to six sites, primarily along the Kaanapali oceanfront beach path.

Clients can also take a self-guided tour with a brochure and map to stop at 10 informational monuments.

The tour begins at the former site of the Kaanapali Airstrip and Terminal at Airport Beach. The guides ask the group to imagine the year 1968, when tourists posted their business cards alongside photos of themselves taken by bartender High School Harry at the former Windsock Lounge.
At the border of the Kaanapali Golf Course a giant boulder resembling the shape of a reclining figure represents the legend of Moemoe, whose listless spirit was given eternal rest after having been turned into stone by the demigod Maui.

In more recent history, the remains of the Kekaa pier can still be seen. The pier served as the docking point for processed sugar transported by railroad from the sugar cane fields and sugar mill. Cut trees for lumber were also cured in the ocean water.

Around that era, from the late 1800s to early 1900s, a horse racetrack dominated the oceanfront at the location now occupied by the upscale Whalers Village shopping center. The races served as a gathering point for the plantation owners, supervisors and laborers; the royalty and local people; and even the missionaries bet on the outcomes.

At a site overlooking an outrigger canoe, the tour guides Krislyn Lavey of Oahu and Kekoa Mowat of Molokai, both employees of the Hyatt Regency Maui sang a canoe chant in Hawaiian used by the warriors. The Hawaiians used canoes for transportation, fishing and warfare. It was easier for them to travel over water to Maui’s neighboring islands of Lanai and Molokai than to trek over land to the far side of the island.

Perhaps the most jarring dislocation of time was when the group crouched through the bushes lining a parking lot while pretending to be warriors entering the famed battleground of Koko O Na Moku. In 1738, the two sons of former chief Kekaulike waged a civil war for future control of Maui. The war ended in the four-day “bloodshed of the islands” battle, in which thousands of warriors perished from stone slings and javelin spears. Their blood flowed down a stream and colored the ocean red for several days. Nowadays, fountains trickle along the green golfing fairways.

The participants were eager to know about this place they had come to for the purpose of relaxing; many had visited Maui a number of years previously.

As one tourist said: “I came here on an island tour 30 years ago. I was young. I didn’t really learn anything.”

This provided the impetus for the Kaanapali Beach Resort Association and its executive director Shelley Kekuna to delve into the predevelopment history of the region and share it with visitors and residents. The newly inaugurated tour is promoted at Kaanapali’s resorts and is open to the community.

The Kaanapali History and Legends Tour enriches anyone’s understanding and experience of Hawaiian culture beyond its resorts, beaches and leisure.


Kaanapali Historical
Trail & History and Legends Tour
Kaanapali Beach Resort Association

A 90-minute guided tour by trolley bus and walking.

Maximum: 21 people
Tuesdays and Fridays starting at 8:45 a.m. Free.

Optional self-guided walking tour with brochure and map to 10 monuments.