By Michael Shapiro
Photography by Kevin J. Miyazaki
Originally appeared in the March 2016 issue of Virtuoso Life.
Third Stone Surfboards at the Waialua Sugar Mill.
’s sprawl, the island of Oahu is as distinctive and diverse as any of its neighbors. The difference: After filling up on miles-long white-sand beaches, epic surf, and awe-inspiring vistas, visitors still have access to some of the country’s finest shopping and dining. Charlene Davé of Virtuoso’s on-site tour operator in Hawaii says, “There’s every imaginable designer store in Waikiki, Ala Moana Center is comprehensive, and Kailua has cute boutiques – plus Oahu has some of the most picturesque beaches in Hawaii.”
For decades Kakaako, near downtown Honolulu, was an urban nowhere of auto dealerships and warehouses, but new luxury condos are attracting upscale shopping and dining to the area. Cap a walking tour of murals by renowned street artists with a visit to Bevy
(661 Auahi Street) for a nonpareil craft cocktail. Every third Saturday of the month, Kakaako hosts the Honolulu Night Market
, with street performances, pop-up shops, vendors, galleries, food, and drink until 11p.m. Park nearby and follow the music.
Chinatown takes Honolulu’s cuisine far beyond Hawaii regional. A contemporary twist on Vietnamese food has made The Pig & the Lady
(83 N. King Street) a popular casual fine-dining restaurant. Seasonal American comfort food and stellar cocktails at Livestock Tavern
(49 N. Hotel Street) are a tasty counterpoint to Asian and Pacific Rim fare. A little east of Chinatown, MW Restaurant
(1538 Kapiolani Boulevard, Suite 107) takes a sophisticated approach to island soul food: ahi poke, mochi-crusted opakapaka (pink snapper), and kalbi.
Shopping, Big and Small.
The world’s largest open-air mall, Ala Moana Center
(1450 Ala Moana Boulevard) continues to grow, with a new wing anchored by Hawaii’s first Bloomingdale’s. In Kailua, a boutique boom means a constellation of shops, several featuring the work of local designers, is within walking distance. Olive Boutique
(43 Kihapai Street) and its neighbor, Oliver Men’s Shop
(49 Kihapai Street), offer bright, beachy women’s- and menswear, respectively. Designer-owned Fighting Eel
(629 Kailua Road, No. 130) carries women’s wear featuring clean lines, classic stripes, and simple tropical prints.
Sugar and Surf.
On the way toward “country” (i.e., the North Shore), the Waialua Sugar Mill
(67-106 Kealohanui Street) is a former sugar plantation mill repurposed as a minimall with around 30 local businesses: woodworkers, soap makers, coffee roasters, and art galleries. Third Stone Surfboard Factory
, one of the North Shore’s oldest, now also houses a gallery and an apparel shop. On Saturdays from 8:30 am to 2:30 p.m., locally grown produce is the draw at the adjacent Waialua Farmers Market
The road up Oahu’s leeward coast ends at Kaena Point Natural Area Reserve
, the island’s northwestern tip. From the trailhead, the 2.4-mile walk to the point parallels a coastline dotted with tide pools and cove beaches. Dolphins and humpbacks cruise offshore; Laysan albatross and the occasional endangered Hawaiian monk seal laze on land. Bring sun protection and plenty of water.
The Longest Strand.
Oahu is blessed with some of Hawaii’s best beaches: Lanikai
’s talcum sands, iconic Waikiki
, and President Obama’s favorite, Kailua
. But for many locals, Waimanalo
– a 25-minute drive from The Kahala Hotel & Resort along the island’s most scenic coastline – is the go-to beach. It’s Oahu’s longest, a four-mile stretch of blue-water-and-white-sand bliss where parking and solitude are easy to find.
Next Page: Kauai
To plan a vacation to Oahu, say aloha to a Virtuoso travel advisor below.
- An iconic pink palace on the shores of Waikiki, the 528-room Royal Hawaiian, a Luxury Collection Resort, recently reinvented its Mailani Tower building, a modern foil to the original 1927 structure, adding an indoor/outdoor reception area and lounge.
- The 453-room Halekulani’s famed orchid pool, Diamond Head views, and prime Waikiki location make it a longtime favorite for Honolulu high life.
- The Kahala Hotel & Resort is the grande dame of Oahu’s south shore. Just east of Waikiki, the 338-room property epitomizes elegance, with a dolphin lagoon and an uncrowded beachfront along Maunalua Bay.
The pool at the St. Regis Princeville Resort.
is the oldest of Hawaii’s main islands, and you can see its ancientness in its stunningly eroded landscapes. With fluted emerald cliffs, taro fields aglow at sunset, and thread-thin waterfalls, the Garden Isle hews most closely to the postcard image of Polynesia. Devotees love its white-sand beaches fronting crystalline lagoons, deliberately downbeat tempo, and emphasis on taking it slow to breathe in the beauty.
Outdoor dining is one of the pleasures of a tropical paradise. Mobile pop-up Kauai Ono
serves local, seasonal, and communal five-course meals under an awning on a grassy field in Princeville. “Bring your own wine,” says Gary Johnson, a Seattle-based Virtuoso agency owner, and reserve well in advance.
Hawaii’s Bali Hai.
Even locals make the evening pilgrimage to The St. Regis Bar
(5520 Ka Haku Road) for spectacular sunsets at the Princeville resort. As the sun drops behind Mount Makana (Bali Hai in the film South Pacific
) at the western end of Hanalei Bay, shafts of light paint the sky orange, pink, blue, and purple. The only thing that can improve on the moment: a signature Blue Kauai from the bar.
Those who prefer a rubber-slipper joint to a hotel bar head to Tahiti Nui
(5-5134 Kuhio Highway), a favorite of Gary Johnson’s. “It’s a hole-in-the-wall that’s been there for 50 years,” he says, “but they have great fish, friendly locals, incredible Hawaiian music every night, and a luau every Wednesday.”
Snorkel and Hike.
Kauai’s rugged topography makes for plenty of outdoor adventure. Snorkel in the lagoon at Ke‘e Beach
(a good spot for kids), then hike the first two miles of the Kalalau Trail along the famous Na Pali Coast to Hanakapiai Beach
(stronger hikers can head up the valley to Hanakapiai Falls). On Kauai’s west side, Koke‘e State Park
has magnificent views of Kalalau Valley and a wealth of native birds and flora.
ON THE WATER
Slow Boat to Wailua.
Hawaii’s longest navigable river is Kauai’s Wailua, and the best way to see it is by barge. Tours have been running up an Edenic two-mile stretch of the river since the late 1940s. One highlight: views of the hanging gardens at Fern Grotto. Passengers are also treated to live Hawaiian music and hula on board; several island musicians launched their careers on the river.
Next Page: Maui
To plan a vacation to Kauai, say aloha to a Virtuoso travel advisor below.
- Surrounded by gardens and water features, the 602-room Grand Hyatt Kauai Resort & Spa in Koloa sits on one of Kauai’s most beautiful coastlines and boasts an 18-hole championship golf course designed by Robert Trent Jones Jr.
- Five miles from Hanalei, the 251-room St. Regis Princeville Resort is the north shore’s most sophisticated property, with a spectacular view of Hanalei Bay and the island’s dramatic coastline.
Decision time at the Letarte boutique in Paia.
There’s a reason the rich and famous (Oprah Winfrey, Clint Eastwood, and Willie Nelson, to name a few) buy homes on Maui
. Some say it’s Oahu without the hassle: just cosmopolitan enough to support superior dining and shopping, but not so urbanized that you can’t find empty beaches and wilderness. Maui’s varied landscapes – Mount Haleakala’s alpine environment, Kaupo’s dry prairie, Hana’s jungles – share an island so small that you can experience all of them in just a few days.
The former sugar town of Paia has become a boutique/bistro/gallery oasis with locally designed fashion. It’s the flagship location for homegrown – and nationally known – Letarte
swimwear (24 Baldwin Avenue). Tamara Catz
(83 Hana Highway) offers Maui-designed women’s swimsuits, clothing, bridal wear, and accessories. Maui Time Weekly
readers have voted island-chic Mahina
(23 Baldwin Avenue) Maui’s best boutique seven years running.
Andaz Maui at Wailea Resort’s Ka’ana Kitchen
(3550 Wailea Alanui Drive) is the apotheosis of Hawaii regional cuisine. Mama’s Fish House
in Paia (799 Poho Place) sources the island’s freshest fish (the restaurant has even installed its own fish-aggregating buoys 20 and 30 miles offshore). And Gary Johnson calls Pacific’O
in Lahaina (505 Front Street, No. 114) “a little gem” where you can dine with the breeze in your hair – on produce sourced from a farm in Kula.
Biggest Is Best.
is my personal favorite,” says Bellevue, Washington-based Virtuoso travel advisor Kari Mollan. Locals call the stretch of white sand on Maui’s south shore “Big Beach” (at two-thirds of a mile, it’s one of Maui’s longest). “It’s so quiet, with no hotels,” she says. “It’s great to get that sense of the real Hawaii.” A tip: For those interested in a snorkel excursion to nearby Molokini Crater
, Mollan suggests the Kai Kanani II
, with pickup at 6:30 a.m. from Makena to arrive when the water’s clearest and before the flotilla of other boats arrives.
ON THE WATER
Pick Your Paddle.
One of the best ways to experience Maui: from the water at paddling pace. Several water-sports operators offer lessons and tours in kayaking, stand-up paddleboarding, and the very Hawaiian sport of outrigger canoeing
. Expect turtles and, often, dolphins. While it’s a federal offense to approach within 100 yards of a humpback whale, it’s no crime if the whale comes to you.
Next Page: Lanai
To plan a vacation to Maui, say aloha to a Virtuoso travel advisor below.
- Wailea’s oceanside Fairmont Kea Lani fronts Polo Beach with 450 one-bedroom suites and two- or three-bedroom villas.
- The 380-room Four Seasons Resort Maui at Wailea has the island’s largest guest rooms and one of its best beaches, with dramatic views of the Haleakala volcano.
- Montage Kapalua Bay houses 56 residences that range from one to four bedrooms, each with private lanais and full kitchens.
Overlanding paradise Garden of the Gods.
It’s said there are two kinds of visitors to Hawaii: those who love Lanai and those who haven’t been there. There’s not much to do on the Pineapple Isle, and that’s the point: On this low-gear tropical sanctuary, time creeps and visitors can relax without the nagging feeling of missing out. “I really love Lanai,” advisor Kari Mollan says. “It’s so quiet, you just want to walk the orchid gardens at Koele or sit in a rocking chair and play chess. Stay for a week, bring a lot of books, and just enjoy it.”
The tranquil island’s recent sale to Oracle boss Larry Ellison means big changes are coming, as he plans to turn Lanai into a model of sustainability, with land restoration, solar farms, and major aquaculture initiatives, among others. Those able to peel themselves from their chaise lounges, however, will still find opportunities for upright fun.
Even in a land of already strange geography, Garden of the Gods
, a few miles northwest of Lanai City, is truly weird: a natural wonder of boulders, spires, and buttes, unique in the Hawaiian Islands. Go in the morning or evening, when the sun casts dramatic shadows across the near-Martian scene. A four-wheel-drive vehicle is required, and moving the rocks is strictly kapu
No Lights, Small City.
An oft-repeated factoid: There are no traffic signals on Lanai, not even in Lanai City. A day trip there, where most of the island’s 3,200 residents live, harbors a few surprises, though. You’ll never go hungry at the Blue Ginger Café
(409 Seventh Street), open every single day for the past 18 years, no exceptions. Lanai Hula Hut
(418 Eighth Street) is a gift shop on a mission, crammed with crystals, jewelry, wind chimes, and more tchotchkes than a quaint country bed-and-breakfast. Recently restored to its 1930s-era charm, the only movie house on the island, Lanai Theater
, runs current releases on state-of-the-art screens.
ON THE WATER
While Hawaii’s diving might not compare to the wonder of Palau’s or Australia’s, Lanai does offer some amazing underwater adventures. Among the best: a pair of sites called the Cathedrals
, named for the way the sunlight streams through the “skylights” of submerged lava tubes. Ask your advisor to make arrangements with the island’s only full-service dive operator through the Four Seasons Resort Lanai.
Next Page: Hawaii
To plan a vacation to Hawaii, say aloha to a Virtuoso travel advisor below.
- The 217-room Four Seasons Resort Lanai is the big hotel and the big news on Lanai. It just reopened following a multimillion-dollar transformation, with new restaurants (including Nobu Lanai), renovated guest rooms and suites, new retail stores, an updated spa, and a refurbished lobby.
The beach at Mauna Kea Beach Hotel.
A place of superlatives and extremes, Hawaii Island (locals are moving away from calling it the “Big Island”) is the United States’ largest island and southernmost point. Site of the world’s tallest mountain (Mauna Kea – 32,696 feet from its seafloor base to its summit) as well as the country’s newest real estate (Kilauea volcano has been adding new oceanfront daily since 1983). The state’s most ecologically diverse island, comprising ten climate zones, from wintry summits to blistering lava deserts. It even has the world’s longest lava tube and the only happy-face spider. Hawaii Island’s otherworldly landscapes and supernatural beauty emanate a tangible vibration, the mana
of a new land forming.
Beauty and Buzz.
The village of Holualoa
is Hawaii’s quaint art center in the heart of Kona coffee country. Get wired and inspired on a self-guided Art and Coffee Stroll
along Mamalahoa Highway. Holuakoa Café
(76-5901 Mamalahoa Highway) is a favorite stop for locavore fare between galleries and roasters.
On the far eastern edge of the islands, Hawaii’s Puna district remains a free-spirited neverland of organic farms, hippie enclaves, and true Hawaiian culture. Every Wednesday night, Uncle Robert’s Awa Bar and Farmers Market
(Kalapana-Kapoho Beach Road) opens in Kalapana. As local as local gets (but friendly to malihini
, or newcomers), the market offers a huge variety of food, live Hawaiian music, and vendors. Dance on a lava field under the stars or sample Hawaii’s chillest beverage: awa
, also known as kava.
Moon Walk. Hawaii Volcanoes National Park
is a national treasure, but few visitors take the time to walk the Kilauea Iki Trail, a moderate four-mile loop through native rain forest alive with rare endemic birds. The highlight: the mile-long section across a lava moonscape – the solid (but still steaming) remains of a lava lake.
ON THE WATER
Into the Abyss.
Few places in the world can guarantee a close encounter with a manta ray, but the Kona Coast is one of them. Every night these gentle giants perform “aquabatics” for experienced divers and beginner snorkelers. Several tours leave from Honokohau near Kailua-Kona. After the manta ray dive
, the intrepid can try the infamous black water night dive
, which takes divers two miles offshore and drops them 40 to 60 feet down – with 2,000 feet beneath them – to drift among the bioluminescent denizens of the big black.
“The stars on Hawaii Island are incredible,” says Virtuoso tour operator Charlene Davé, who recommends heading up to the Mauna Kea summit
on a stargazing tour. Standing under the glittering Milky Way, you can see why the peak hosts the world’s most sophisticated observatories. Tours offer stargazers “the chance to learn about the stars from a native Hawaiian perspective as well as a modern scientific one,” she says. Don’t worry about the cold (it will
be cold!); tour operators provide parkas.
To plan a vacation to Hawaii, say aloha to a Virtuoso travel advisor below.
- In addition to having an exquisite art collection and a commitment to Hawaiian-inspired design, the 243-room Four Seasons Resort Hualalai is home to one of the country’s best golf courses, designed by Jack Nicklaus.
- Laurance Rockefeller founded the 252-room Mauna Kea Beach Hotel on the Kohala Coast in 1965. It’s home to a Robert Trent Jones Sr.-designed golf course, biweekly luaus, and an inviting sweep of beach.