Early in 1939, Georgia O’Keeffe, the artist most famous for depicting the arid Southwest, suddenly decided to paint America’s diametrically opposite landscape: the lush tropical valleys of Hawaii. In an era when advertisers often hired fine artists to add a touch of class to their campaigns, the "least commercial artist in the U.S." (as Time magazine described O’Keeffe) was persuaded by the Dole pineapple company to visit the remote Pacific archipelago and produce two canvases.

The offer came at a critical time in O’Keeffe’s life. She was 51, her career seemed to be stalling (critics were calling her focus on New Mexico limited and branding her desert images "a kind of mass production") and her marriage to Alfred Stieglitz was strained.

Despite initial reservations about the project, her many letters back home show that her experience of the then little-known territory of Hawaii was a revelation. O’Keeffe ended up spending nine weeks on different islands, of which by far the most productive and vivid period was on Maui, where she was given complete freedom to explore and paint.

On Oahu, where she had first arrived, she had been incensed that Dole officials refused to let her stay on a working pineapple plantation because it was unseemly for a woman. When they delivered to her hotel a pineapple already peeled and sliced, she tossed it out in disgust. But on Maui she was able to seek an unfiltered view of nature and went directly to the port of Hana, the most remote, wild and verdant corner of the island.

She reported to Stieglitz about Hana’s dark rain forests, exuberant flora, black-sand beaches and lava washed into "sharp and fantastic shapes." Staying on the Kaeleku sugar plantation, the notoriously prickly artist was given Patricia Jennings, the 12-year-old daughter of the plantation manager, as her private guide, and the two became unlikely friends. For 10 days the pair visited sea caves, ruins and beaches, and later, with Patricia’s father, made excursions to the dramatic Iao Valley and Haleakala Crater.

I first stumbled across this exotic biographical interlude in the New York Public Library, where I found a 1990 catalog for an exhibition of O’Keeffe’s Hawaii paintings at the Honolulu Academy of Arts, now called the Honolulu Museum of Art. The images of emerald chasms, gleaming waterfalls and brilliantly tinged bird of paradise flowers were the very essence of the tropics. Then, just this past spring, Koa Books released "Georgia O’Keeffe’s Hawaii," co-authored by Jennings (now an octogenarian grandmother) and filled with memories of her time with the artist.

When I returned to Maui recently, I wondered if Jennings might agree to be a virtual tour guide and help me follow in O’Keeffe’s footsteps. She lives far from Hana, on Hawaii island, and rarely travels, although her memories of her time with the artist are still vivid.

"You never saw a single tourist in the old days," she said by the telephone, as I jotted down their itinerary. "Even at the most beautiful spots, we were always the only ones there."

Today, of course, Hana is one of the most famous destinations in Hawaii, but few people spend the night there. Most travelers base themselves at beach resorts on the other side of the island, so they rush the 53-mile drive from Kahului (as much as they can rush considering there are more than 50 bridges, most of them one-lane, and some 600 hairpin bends) and then, pressed for time, are forced to return soon after.

HANA TOWN today is so sleepy you could miss it. When I arrived, its half-dozen streets above the bay were eerily quiet, except for the occasional cheer from a baseball tournament. I pulled in to the Travaasa Hana, the only resort in town. Facing the forest-covered headland of Kauiki, the hotel’s manicured lawns and serene tropical gardens seemed even more detached from the rest of the world. From there I could explore many of the places O’Keeffe visited, with a car and often on foot.

When O’Keeffe arrived, Hana was a thriving community of 3,500 people. Its six sugar plantations attracted a cosmopolitan mix of Japanese, Chinese, Filipinos, Portuguese, Pacific islanders and Native Hawaiian workers, with two cinemas, three barbershops, several restaurants and a pool hall. Although the last plantation closed in 1946, memories of the glory days linger. On the volcanic sand beach, a crumbling jetty still extends into the surf, with railway tracks for loading the sugar boats still visible.

I sought out the Hasegawa General Store, run by the same family who ran it back when O’Keeffe was there. It was here where she bought the broad-rimmed straw hat she is seen wearing in photographs, grinning like a carefree teenager. (Ansel Adams once noted, "When O’Keeffe smiles, the earth cracks open.")

Patricia said that she has never forgotten the moment O’Keeffe arrived after the grueling all-day drive. With her mother away on the mainland, the 12-year-old was terrified of meeting the notorious artist, who had caused a sensation by posing nude for Stieglitz; a heavily cropped image had made it to Hana in the pages of Time.

"Georgia said absolutely nothing; she was stony-faced as she got out of the car," Patricia said.

When shown her cottage, O’Keeffe said only, "Yes, it’s very nice."

But at dinner in the plantation house with four male officials, she suddenly transformed herself.

"I had to marvel, the men were just enthralled," Patricia recalled. "I thought in order to be attractive, a woman had to be pretty. Now here was Georgia, very plain, with no makeup on and a dull dress, but when she got to talking, she bloomed."

Patricia also distinctly recalls her handsome father, Willis, and Georgia exchanging glances. A couple of nights later, she saw them walking hand in hand in the moonlight.

"I guess I grew up a lot in those few days," she said, and laughed.

Today the plantation house is still tucked away in a corner of the Travaasa, which uses it for group events. I ascended a lane toward the hills above the Hana store and, sure enough, spotted the elegant home, recognizable from photographs. Behind it, one of three original cottages survived as a caretaker’s shed, but the one in which O’Keeffe stayed is gone.

"You would laugh to see where I am now," O’Keeffe wrote in one of her daily letters to Stieglitz, describing the dazzling glimpses of the blue Pacific through the sugar cane and the ever-present smell of molasses from a nearby refinery.

She explored the tropical grounds, with its mango, lychee, tamarind, starfruit and avocado plants.

It was from this idyllic base that Patricia and Georgia departed every morning on daily excursions in a company car. Despite O’Keeffe’s stern nature — which included an aversion to Patricia’s beloved pet dog — the artist became intrigued by this barefoot tomboy growing up at the end of the world. Once, when it was raining, O’Keeffe allowed Patricia to climb into the car and watch her paint in the front seat, a sight strictly forbidden to other mortals.

SOME OF THE places O’Keeffe visited are now major tourist attractions, but staying in Hana meant that I could visit before all the day-trippers arrived. A stunning cascade of natural swimming holes at Oheo Gulch are now part of Haleakala National Park and by noon are crowded with frantic visitors. At 9 a.m., however, I could dive into the most inviting pool with just a few campers for company, protected from the crashing ocean by a ring of lava rocks, and picture O’Keeffe standing on the banks with her easel.

On occasion, following the O’Keeffe itinerary led to minor adventures. She had written to Stieglitz about swimming in a cave near the beach at Waianapanapa State Park, and Patricia had described it, too. After scrambling through foliage above the black sands, I ran into two Hana residents named Gina and Terry, who pointed me in the right direction.

"You can swim under a ledge and find two carved Hawaiian thrones," Gina said. "It’s pretty trippy."

The cave was just as Patricia had described it, filled with crystalline water that reflected the overhanging ferns. I eased myself into the icy pool and breaststroked toward a dark recess on the left, trying not to jump whenever a palm frond brushed across my legs. Soon I was in total darkness, as complete as a sensory deprivation tank. I had already learned that on Maui one should always carry a swimsuit and water shoes to prepare for any eventuality. Now I realized I should also carry a flashlight.

I dashed up to the car and dug out my headlamp. Swimming back into the void, the light revealed two rocky outcrops poised above the waterline that did indeed resemble thrones. According to the Hawaiian legend, this was where a beautiful princess and her maid hid from a jealous king, until he found and killed them both in a rage. (Despite O’Keeffe’s claims in her letter, Patricia had assured me that Georgia stayed on dry land. "I had the feeling she was actually afraid of water. She always sat on the sand at the beach and was even terrified of crossing a stream 6 inches deep.")

Then there were the coastal hikes.

"Georgia did like to walk!" Patricia had told me.

And she memorialized what she found in her work. O’Keeffe painted two lava bridges — natural arches formed over the crashing waves of the ocean below. Finding the first was not hard. It’s visible from the parking lot on the cliffs of Waianapanapa Beach. But to find the second, I set off on the coastal trail south of Hana, where I was whipped by sea spray as I traversed several farms where cows stared at me and dogs yapped at my heels. After about 45 minutes, I spotted the lava bridge. A Hawaiian family was camping next to it, with teenage boys casting fishing lines from precarious rocks nearby.

One of the last places Patricia had told me about was an ancient heiau just north of town that she said she had visited with O’Keeffe. I found the dirt road she had described but no signs to an archaeological site, so I eventually flagged down a truck being driven by three tattooed farm girls. They informed me that the temple, Piilanihale Heiau, was inside Kahanu Garden, one of five sites that make up the National Tropical Botanical Garden, created to study tropical plants.

BACK in Manhattan, O’Keeffe completed a series of 20 sensual, verdant paintings. Dole advertising executives were exasperated to learn she had painted almost everything except pineapples, including papaya trees, heliconia plants and even fishhooks. So the company had a whole fresh pineapple couriered to her by seaplane, which she graciously did paint. ("It’s beautiful," she conceded disingenuously to a reviewer at Time. "It is made up of long green blades, and the pineapples grow on top of it. I never knew that.")

Artistically, the trip was a success, and Stieglitz’s Madison Avenue gallery, An American Place, was turned into a "madhouse" by fans eager to see the new collection — a "health-giving" dose of Pacific color and sunshine — when it was displayed in the freezing February of 1940. The critic for the New York Sun noted that the works "testify to Miss O’Keeffe’s ability to make herself at home anywhere."

Patricia never saw Georgia again, but they did correspond for a time.

"I will always remember you as a little girl," O’Keeffe wrote in one fond letter, "a very lovely little girl — in a sort of dream world."

Tony Perrottet is a contributing writer for Smithsonian Magazine.