Julia Flynn Siler

By JULIA FLYNN SILER

Since Captain James Cook first reached the Hawaiian islands in 1778, waves of visitors have followed the British explorer to Hawaii, hoping to experience the islanders’ famous aloha spirit. Cook himself was initially greeted with kindness, but on his second trip to Hawaii in 1779, the navigator fell into a dispute with native Hawaiians over a stolen canoe. After being stabbed and clubbed, he plunged face-first into the Pacific and died.

Hawaii may seem like a tropical idyll, but its long history of conflict between locals and foreigners—who are known by the Hawaiian term “haole” (pronounced howl-eee)—is never far from the surface. Part Polynesian, part Asian, part military base, part honeymoon destination, Hawaii’s capital of Honolulu, located on the southeastern side of Oahu island, is arguably the most foreign of U.S. cities, as well as one of the loveliest.

Waikiki Beach, once a retreat for Hawaii’s kings and queens, remains famous for its warm waters and gentle surf. About three miles away is Honolulu’s downtown, with its thriving arts scene. Coral reefs and tropical rain forests are within easy reach. For those seeking three days that feel like three weeks away from the mainland, Honolulu is a paradise of contradictions.

DAY ONE

Friday

8 p.m. Land at Honolulu International Airport. Renting a car is a must if you plan to explore other parts of Oahu. Just 597 square miles, the island is home to nearly a million people, most of whom live in Honolulu. Consider getting a GPS, since Hawaiian street names can be confusing.

8:30 p.m. Check into the Halekulani Hotel (halekulani is Hawaiian for the “house befitting heaven”), a beachfront bastion of calm amid the bustle of Waikiki. Take a seat in the open lobby and feel the trade winds blow through (from $490 a night, 2199 Kalia Rd., halekulani.com).

9 p.m. Stroll a few blocks over to Morimoto Waikiki, Iron Chef Masaharu Morimoto’s outpost in the Modern Honolulu hotel (1775 Ala Moana Blvd., morimotowaikiki.com ) where stylish locals gather. Sip on a Morimo-Tai, Mr. Morimoto’s kaffir-lime-infused version of the classic Mai Tai, as you gaze on the Pacific. Try the chef’s version of such local favorites as poke (a raw fish dish, pronounced po-kay; his is made with an avocado wasabi sorbet and dashi foam) and loco moco (typically a scoop of white rice, topped with a hamburger patty, fried egg and gravy; his Loco Moto is made with wagyu beef and hayashi gravy).

10:30 p.m. Hawaii Kotohira Jinsha-Hawaii Dazaifu Tenmangu, a cluster of seven Shinto shrines that are gearing up for Hatsumode, the Japanese tradition of the first visit to the shrine in the New Year. Join the crowds to pray for positive energy and to burn last year’s fortunes. The festivities will include traditional Japanese lion dancing, known as shishimai. Year round, stop in for omamori (wearable Japanese charms dedicated to Shinto deities) from 8 a.m. to 4 p.m. daily ( e-shrine.org ).

DAY TWO

Saturday

8 a.m. Step outside the hotel and start your day with a swim off the beach. Watch the sun rise from behind the mountains to the east, gilding Leahi, better known as Diamond Head, the volcanic crater that is Honolulu’s most distinct landmark. Float on your back, look at the sky and cast off your mainlander’s cares.

After your swim, stroll down the beach past the Royal Hawaiian hotel, known as the “Pink Palace,” to the lei-garlanded statue of Olympic swimmer and surfer Duke Kahanamoku. Here you can rent surfboards, paddleboards and fins or arrange a surfing lesson with one of Waikiki’s famed beach boys. If you prefer a quieter spot, it’s a 1.8-mile walk from the Halekulani to a fine stretch of Waikiki known as Sans Souci, near where, in 1889, Robert Louis Stevenson, the Scottish author of “Treasure Island,” penned a poem for the Hawaiian princess Kaiulani.

9 a.m. The popular KCC farmer’s market is located at Kapiolani Community College (Parking Lot C, 4303 Diamond Head Rd., hfbf.org/markets/markets/kcc ). Here you’ll find a rainbow of local growers and producers, including Hanalei Taro & Juice Co. from the nearby island of Kauai. It offers such treats as muffins made with banana and poi (mashed taro root) and tropical taro smoothies. Each Saturday, a different local restaurant offers a heaping hot-plate breakfast and there’s often a popular stand selling fried green tomatoes. The lines can get long, so try to get there before the tour buses do.

10 a.m. Soak up royal history in downtown Honolulu, where you’ll find Iolani Palace (364 South King St., iolanipalace.org ), the former seat of the Hawaiian monarchy. The 1882 palace is a graceful contrast to the 1960s Bauhaus-style state capitol building, with its palm-shape columns. Iolani Palace, named after the Hawaiian word for “bird of heaven,” is an Italianate gem and currently serves as a cultural repository for some of the most beautiful and striking objects in Hawaiian history (including a recently donated 13.88-carat diamond ring that once twinkled from King Kalakaua’s pinky).

Be sure to head up to the second floor and the newly restored “Gold Room,” where two remarkable paintings from Hawaii’s Volcano School now hang—the oil landscape of a fiery lava flow titled “Halemaumau Crater, Kilauea Volcano,” painted by Jules Tavernier, and Charles Furneaux’s view of Diamond Head. The palace’s most poignant treasure is the quilt that the deposed Queen Liliuokalani stitched in 1895 with her ladies-in-waiting while she was imprisoned in the palace for eight months following a failed attempt to restore her to the throne.

Across the street from the palace is the statute of King Kamehameha I, the great warrior chief who united the archipelago’s eight large islands in 1810. (You might experience déjà vu; this artwork is in the opening sequence of the remake of the television series “Hawaii Five-0.”)

Noon Walk a few long blocks to the Honolulu Museum of Art (900 S. Beretania St., honolulumuseum.org ) and take a quick peek upstairs at the permanent Hawaiian collection, including more paintings from the Volcano School. Founded in 1927 by Anna Rice Cooke, the daughter of two of the first Christian missionaries to the islands and daughter-in-law of Queen Liliuokalani’s childhood teachers, this institution is where Honolulu’s elite often lunch.

Join them at the museum’s outdoor cafe, which features a 75-year-old monkey-pod tree and the modern sculptures of Japanese ceramicist Jun Kaneko. Reservations are recommended (808-532-8734) and hours for lunch are short (11:30 a.m.-1:30 p.m.). Aim for a noon seating, which will give you plenty of time to make the 1:30 p.m. tour of Shangri La, tobacco heiress Doris Duke’s tropical estate. Tucked away on a back street of Black Point, an exclusive neighborhood near Diamond Head, the estate opened its Damascus Room, an extraordinary 18th-century Syrian interior with gilded and painted wooden ceilings, to the public for the first time in July. Be sure to make a reservation for the Shangri La tour ($25 general admission) by calling or booking online with the Honolulu Museum of Art, which operates the estate ( shangrilahawaii.org ).

Ms. Duke collected some 2,500 objects of Islamic art and hired local craftsmen in Honolulu to complete and install them in the house. The guesthouse she called her “Playhouse” and the 75-foot saltwater pool overlooking the sea are particularly spectacular.

6 p.m. Head back to the Halekulani Hotel for drinks at the House Without a Key, an oceanside venue named after the first Charlie Chan mystery novel, written in 1925 by Earl Derr Biggers (and later made into a series of Hollywood movies). Every evening from 5:30 to 8:30 p.m., Kanoe Miller and other dancers perform hula to Hawaiian music, all against the backdrop of a gnarled, century-old kiawe tree that was planted during Queen Liliuokalani’s lifetime.

8 p.m. Venture mauka (Hawaiian for “toward the mountains”) to chef Ed Kenney’s restaurant Town (3435 Waialae Ave., townkaimuki.com ) for a complete shift in tone. Set in the modest neighborhood of Kaimuki and surrounded by small shops and homes, it is a revelation of organic, farm-to-table cooking. Mr. Kenney was born on Oahu to singer Edward Kenney, Jr., and hula dancer Beverly Noa, who used to headline shows at the Halekulani and Royal Hawaiian hotels. Now, their son is headlining a new wave of island chefs sourcing their ingredients locally—to spectacular effect. Try his tombo ahi, a fresh-caught albacore tuna on a bed of green lentils. Don’t bother dressing up: The vibe is surfer chic.

DAY THREE

Sunday

9 a.m. Pack a swimsuit, towel, umbrella and comfortable shoes. Jump in your car and head inland to the Liliha Bakery, in the neighborhood of Kalihi, for its famous coco puff pastries (now available in a green tea flavor). If you want something a little more substantial, take a seat at its coffee shop for Portuguese sausages and eggs and grilled mahi-mahi (515 N. Kuakini St., lilihabakeryhawaii.com ).

10:30 a.m. Drive about 45 minutes northeast on the Kamehameha Highway, passing through former sugar fields now planted with cacao, until you reach Haleiwa Surf N Sea ( surfnsea.com ), one of the town’s original surf shops. If the weather is good, rent a stand-up paddleboard ($55 for an introductory 1-hour lesson) and head up the relatively calm waters of the Anahulu River or hire a surf safari guide to lead you to some of the North Shore’s famed surfing spots ($220 for 4-5 hours). Monster waves—some as high as 80 feet—can pummel this side of the island during the winter. Be cautious heading into unfamiliar waters: The North Shore is not for amateurs.

Noon Request an outside table at nearby Haleiwa Joe’s (66-011 Kamehameha Highway, haleiwajoes.com ) for a bite to eat—be sure to check out the photos and vintage surfboards of big-wave surfing legends on the wall. If it’s too crowded, try the low-key Coffee Gallery (66-250 Kamehameha Highway, in the North Shore Marketplace, roastmaster.com ), a local favorite that brews its coffee from locally grown beans. For dessert, head over to Matsumoto Shave Ice ( matsumotoshaveice.com ) for the Hawaiian special (pineapple, coconut and banana). Jump in your car and head about five miles up the highway to the Waimea Valley (59-864 Kamehameha Highway, waimeavalley.net ), a site sacred to native Hawaiians. Not only is Oahu’s largest temple located nearby at Pu’u o Mahuka Heiau State Monument, but so are the archeological remains of some 78 ancient religious sites and shrines, as well as fishponds, and a waterfall and pool where you can swim. The 1,875-acre site is a refuge to native and endangered plants, birds and fish. Now owned by a non-profit entity formed by the Office of Hawaiian Affairs, the garden has daily events that include guided hikes, music and an opportunity to visit with local kupuna (elders). Be prepared for sudden downpours. Rainbows are also likely here, as this is the wet, windward side of the island.

4 p.m. Drive west along the coastline from Waimea Bay toward the Pali Highway. Along the way, you’ll see an Oahu that’s startlingly different from urban Honolulu. You might see some of the shore’s famed big waves or, even better, the adrenaline-fueled athletes who live to tame them at such famed surfing sites along the way as the Banzai Pipeline at Ehukai Beach Park and Sunset Beach. If you get hungry, stop at one of the many trucks selling garlic shrimp. It’s about an hour drive to the top of the Nuuanu Pali Lookout, the 1,000-foot cliff where hundreds of Oahu warriors plunged to their deaths in a key battle against warriors from Hawaii’s Big Island in 1795 in King Kamehameha’s effort to unify the islanders. You’re in for a breathtaking view, so long as the clouds lift.

8 p.m. Head back to your hotel, shower, and get ready for a treat: dinner at Sushi Sasabune (1417 S. King St.), a meal so good that fans fly from the mainland to eat here. It’s omakase-style: Obey the chef and eat what’s served, in the way you are instructed by your wait staff. The nearly translucent slices of yellowfin tuna are sublime.

DAY FOUR

Monday

7 a.m. Get ready for a boat trip up the rugged Waianae Coast on the leeward side of the island, an area that most visitors never see but should. It is a 40-minute drive to the harbor (85-371 Farrington Highway, Waianae), so on the way, stop by Leonard’s Bakery (933 Kapahulu Ave., Honolulu, leonardshawaii.com ) for its justifiably famed malasadas—a Portuguese deep-fried confection, like a jelly donut. Served warm and covered in sugar, they tend to be filled with a mango cream this time of year.

8 a.m. When you arrive at the harbor, you’ll meet your captain from Wild Side Specialty Tours, as well as a crew person with a background in marine biology ($195 per person for 3½ hours with a maximum of six people, sailhawaii.com ). Swimming with spinner dolphins and snorkeling to a colony of green turtles could be the highlight of your vacation, particularly if you see breaching whales or a rare, endangered Hawaiian monk seal snoozing on the beach along the way. If you’re lucky enough to spot a seal, don’t make an approach: They can be aggressive. You’ll pull back into the harbor before noon.

Noon On your way to the airport, stop at Pearl Harbor to visit the U.S.S. Arizona Memorial (timed entries run from 8 a.m. to 3 p.m.; make reservations online beforehand since they frequently sell out, recreation.gov ). It is a haunting site: The U.S.S. Arizona was a warship sunk on Dec. 7, 1941, during the Japanese attack on Pearl Harbor. More than 1,000 crew members lost their lives. If you have time for a late lunch, try Alan Wong’s Pineapple Room (1450 Ala Moana Blvd. alanwongs.com ), a casual restaurant headed up by a pioneer of Hawaiian regional cuisine. Order the Kalua Pig “BLT” and Mamaki Iced Tea. Buy a lei made from plumeria blossoms at the airport. Breathe in the fragrance of the islands one last time before saying aloha.

—Ms. Flynn Siler is the author of “Lost Kingdom: Hawaii’s Last Queen, the Sugar Kings, and America’s First Imperial Adventure” (Grove Press) out in paperback in January.

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