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Hawaii is a bucket-list-topping dream destination for so many people. Its iconic, description-defying scenery, captivating culture, and laidback island lifestyle are just part of the allure. There are also the beaches, the surf, volcanoes, spectacular hikes, famous movie settings, and, let's not forget the food. From street food to world-famous chefs, Hawaii's thriving dining scene is itself a draw.
Each island is unique - they all have differing topography, attractions, and identities. There's so much to explore and it's not a destination to rush through. We recommend one or two islands tops if you're staying a week. The tough question - which to choose? That depends on what you're looking for.
Kauai
Kauai 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.
Tiki Fix
Those who prefer a rubber-slipper joint to a hotel bar head to Tahiti Nui, a decades-old hole-in-the-wall that's where you'll find 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 kid-friendly Ke'e Beach, 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.
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.
Where to Stay
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. Virtuoso travelers receive breakfast daily and a $100 resort credit.
Oahu
Beyond Honolulu'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 have access to some of the country's finest shopping and dining.
Kakaako Rising
Kakaako near downtown Honolulu was an urban wasteland of auto dealerships and warehouses for decades, 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 for a nonpareil craft cocktail.
Chinatown Dining
Chinatown takes Honolulu's cuisine far beyond Hawaii regional. A contemporary twist on Vietnamese food has made The Pig & the Lady a popular casual fine-dining restaurant. Seasonal American comfort food and stellar cocktails at Livestock Tavern are a tasty counterpoint to Asian and Pacific Rim fare. A little east of Chinatown, MW Restaurant takes a sophisticated approach to island soul food: ahi poke, mochi-crusted opakapaka (pink snapper), and kalbi.
Sugar and Surf
On the way toward "country." or the North Shore, the Waialua Sugar Mill 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, also houses a gallery and an apparel shop. On Saturdays from 8:30 a.m. to 2:30 p.m., locally grown produce is the draw at the adjacent Waialua Farmers Market.
Go Wild
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.
Where to Stay
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. Virtuoso travelers receive breakfast daily and a $100 resort credit.
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. Virtuoso travelers receive a welcome amenity, breakfast daily, and a $100 dining credit.
Maui
There's a reason rich and famous folk like Oprah Winfrey, Clint Eastwood, and Willie Nelson buy homes on Maui. Some say it's Oahu without the hassle: 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.
Locavores Rejoice
Andaz Maui at Wailea Resort's Ka'ana Kitchen is the apotheosis of Hawaiian regional cuisine. Mama's Fish House in Paia sources the island's freshest fish, thanks in part to its fish-aggregating buoys sitting 20 and 30 miles offshore. Pacific'O in Lahaina is a beachfront gem featuring farm-to-table and locally inspired recipes.
Biggest Is Best
Makena Beach, a stretch of white sand on Maui's south shore, is known to locals as "Big Beach." At two-thirds of a mile, it's one of Maui's longest beaches, and with no hotels, one of the quietest. For a snorkel excursion to nearby Molokini Crater, check out the Sunrise Snorkel Tour with Kai Kanani II. Their early morning departure will have you in the crystal-clear waters before the flotilla of other boats arrives.
Pick Your Paddle
One of the best ways to experience Maui is from the water at a 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.
Where to Stay
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. Virtuoso travelers receive a welcome amenity, breakfast daily, and a $100 dining credit.
Montage Kapalua Bay houses 56 residences ranging from one to four bedrooms, each with private lanais and full kitchens. Virtuoso travelers receive a welcome amenity, breakfast daily, and a $150 spa credit.
Lanai
It's said there are two kinds of visitors to Hawaii: those who love Lanai and those who haven't been there. Time passes slowly on this low-gear tropical sanctuary, allowing visitors to relax without the nagging feeling of missing out. It's the ideal spot to slow down by walking the orchid gardens at Koele or curling up in a rocking chair with a good read.
The tranquil island's 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. Those able to peel themselves from their chaise lounges, however, will still find opportunities for upright fun.
Rock Garden
Even in a land of strange geography, the Garden of the Gods on the northwest side of the Lanai is truly weird. This natural wonder, a lunar landscape populated with boulders, spires, and buttes, is 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 – forbidden.
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, open every single day for the past 18 years, no exceptions. Lanai Hula Hut 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.
Divine Diving
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.
Where to Stay
The 217-room Four Seasons Resort Lanai is the big hotel and the big news on Lanai. It recently reopened following a multimillion-dollar transformation, with new restaurants, renovated guest rooms and suites, new retail stores, an updated spa, and a refurbished lobby. Virtuoso travelers receive a welcome amenity, breakfast daily, and a $100 dining credit.
Hawaii Island
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. It's home to Mauna Kea, the world's tallest mountain at 32,696 feet from seafloor base to summit. Hawaii Island is also continuously expanding its real estate, thanks to Kilauea Volcano, which has been adding new oceanfront daily since 1983. The state's most ecologically diverse island comprises 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.
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 a 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.
Into the Abyss
The Kona Coast is one of the few places in the world that can guarantee a close encounter with a manta ray. 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.
Get High
Head 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. Don't worry about the cold - and it will be cold! - tour operators provide parkas.
Where to Stay
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. Virtuoso travelers receive a welcome amenity, breakfast daily, and a $100 dining credit.
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. Virtuoso travelers receive breakfast daily and a $100 hotel credit.
Contact me to start planning your escape to the Aloha State, complete with exceptional experiences.
Produced by Virtuoso, Specialists in the Art of Travel and Grand Journeys Travel
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