The experts’ guide to planning a trip to Hawaii


Americans can now travel to Hawaii’s beautiful tropical shores without having to quarantine on arrival.

From Oct. 15, domestic travelers who take part in the state’s Pre-Travel Testing Program can bypass a two-week quarantine requirement, provided they test negative for Covid-19 before and, in some cases, after they arrive.

“After not being able to travel for so many months, people are eager to get away for a much-needed vacation, and Hawaii is an easy and quick destination to reach,” said Nancy Herron, the owner of Island Journeys, a travel agency that specializes in trips to Hawaii.

CNBC’s Global Traveler spoke with Herron and another Hawaiian travel expert for advice on where to go and what to do while visiting the Aloha State.

Understanding the islands

The Hawaiian archipelago comprises 137 islands, but travelers mainly go to six:  

·       Oahu
Nickname: The Gathering Place
Oahu is home to the state capital of Honolulu, the historical sites of Pearl Harbor and iconic Waikiki Beach. Though more than two-thirds of Hawaii’s total population lives there, quiet areas abound, with palm tree-lined postcard versions of Hawaii outside of the bustling towns.

A map of Hawaii.

Artbyjulie | DigitalVision Vectors | Getty Images

·       Maui
Nickname: The Valley Isle
Hawaii’s second-largest island attracts 13 tourists per year for every resident. Home to around 150,000 people, Maui has the nightlife and entertainment of Oahu without the big city feel. Some of Hawaii’s best golfing and restaurants are here, as are scores of art galleries, waterfront shops and luxury hotels.

·       Hawaii
Nickname: The Big Island
Hawaii’s largest island, often referred to by its nickname to avoid confusion with the state, is smaller in size than Connecticut. It’s got history, white sand beaches, rainforests, coffee farms, waterfalls, lava beds and one of the planet’s most active volcanoes — Kilauea

·       Kauai
Nickname: The Garden Isle
The least populated of Hawaii’s larger islands is quiet, relaxed and popular for outdoor adventures, be it cruising the Napali Coast, exploring the underwater lava tubes of Tunnels Beach or hiking the Kalalau Trail.

·       Molokai
Nickname: The Friendly Isle
At half the size of Kauai, this island is popular with day-trippers from Maui, who seek out its old-school rural Hawaii ambiance. Overnight travelers can stay in condo rentals, guesthouses or several rustic resorts.

The untouched terrain of Molokai is one of its biggest draws.

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·       Lanai
Nickname: The Pineapple Isle
This tiny island once known for its pineapple plantations is now the playground of Oracle co-founder Larry Ellison, who bought most of it in 2012 for $300 million. It’s peaceful and popular with affluent travelers for its two Four Seasons resorts, one along the beach and the other hidden in the highlands.

Pick an island (or two)

When choosing which islands to visit, travel experts say less is more.

“I recommend coming to Hawaii for two weeks and visiting two islands,” said Karen Frangipane, a senior manager at Honolulu-based Luxe Travel Hawaii.  “If you only have one week, then I would suggest picking one island that best suits your personality.”

Herron of Island Journeys said she helps travelers visit two islands in one week if “they insist.” While traveling between the islands is easy, she said, it still “pretty much takes up a whole day.”

Commercial flights can be as short as 30 minutes, while passenger ferries link Maui to Lanai (45 minutes) and Molokai (90 minutes). Yet, travelers must factor in transit and waiting times as well as hotels check-in times which can be as late as 4 p.m., said Herron.

Interisland travel in Hawaii via commercial flights or chartered airplanes is easy, though it can take more time than travelers expect.

Fabrizio Gandolfo | PA Images | LightRocket | Getty Images

“For first-time travelers to Hawaii … I might recommend two to three nights in Waikiki and four or five on a neighbor island,” said Herron.

Cruise ships are the exception to the “one island per week” rule. Norwegian Cruise Line’s Pride of America originates from Honolulu and visits four Hawaiian Islands in a week. The ship is scheduled to cruise again on Dec. 5.  

“I recommend Uncruise Adventures for more affluent and educated cruisers,” said Herron. “This ship is small which allows for it to visit areas the larger cruise ships cannot reach including an up-close-and-personal stop on the island of Molokai.”

Choose your adventure

Though the Hawaiian Islands are mountain peaks from the same underwater mountain range, each island has topography and corresponding activities of its own.  

Outdoor enthusiasts:

Serious golfers should head to the Big Island or Maui. Herron recommends the oceanfront Mauna Kea Golf Course and the Hualalai Golf Course, the latter a Jack Nicklaus Signature course open to guests at the Four Seasons Resort Hualalai. Two of the best courses on Maui are The Plantation Course and the Wailea Emerald Course, said Frangipane.

Makahiku Falls in Maui’s Haleakala National Park.

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Hikers can’t go wrong on any island, but the lush North Shore of Kauai, barren lava beds of Maui’s Haleakala National Park and the Big Island’s waterfall laden Waipio Valley are Herron’s top picks.

If surfing is too demanding, a company called LightSUP Hawaii has sunset paddleboard tours to spot manta rays off the Big Island. “After the sun sets, your paddleboard lights up revealing the sea life below through the ‘window’ in your board,” says Herron, who refers to the experience as “magical.”


Tandem ziplining, kayaking, night diving and helicopter tours will appeal to thrill-seekers who want to see Hawaii from the perspective of the land, sea and sky.

Kids as young as five can tube down the canals of Kauai’s old sugar plantations. Families can also charter a crewed catamaran through Trilogy Excursions for a day of swimming, whale watching and “snuba” diving, a cross between diving and snorkeling, said Herron.    

The finer things:

One of the biggest draws to Lanai is its hotels — there are but three. A full day of pampering at the spa at the new Sensei Lanai, A Four Seasons Resort is the ultimate luxury indulgence. The hotel is one of Herron’s favorites, along with the Big Island’s Four Seasons Resort Hualalai.

Frangipane agreed with those choices, adding in Maui’s Fairmont Kea Lani, which is opening Nov. 1, and the Halekulani near Waikiki Beach.

The pool at the Four Seasons Resort Lanai overlooking Hulopoe Bay.

Barbara Kraft | Four Season

Car enthusiasts can navigate Hawaii’s serpentine island roads in a Porsche Boxster, Maserati or Tesla, while those who prefer the thrill of two wheels can rent a Harley-Davidson on Oahu, Kauai or the Big Island.  

Mama’s Fish House may sound casual, but it’s one of northern Maui’s top spots for fresh seafood. Herron advises diners to reserve a window seat early and arrive 30 minutes below sunset.

Serene and socially distanced:

Every island has places for peace and reflection, said Frangipane, but she highlights Oahu’s North Shore, Maui’s Road to Hana, Kauai’s historic town of Hanalei and the lush areas around Hawi on the Big Island as standouts.  

Be prepared for closures

Though the islands have opened, some of its most famous sites have not.

The historic sites of Pearl Harbor are currently closed. When they do open, allocate at least half a day to see the warships, with additional time to test a flight simulator at the Pearl Harbor Aviation Museum.

Oahu’s Polynesian Cultural Center is also closed. Reopening efforts have been hindered by the fact that more than 70% of its staff are students of Brigham Young University-Hawaii, which moved to online classes in March, according to its website.

Hawaii Volcanoes National Park is open though ranger-guided hikes are currently suspended.

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Visitors may have more luck at Hawaii Volcanoes National Park. The park is open, but the Kilauea Visitor Center and Thurston Lava Tube remain closed.

“The best way to visit the volcano is by helicopter, boarding either in Waikoloa or in Hilo,” said Herron. Helicopter tours are currently operating.

Large luaus are restricted right now too, but a more upscale alternative can be found at Maui’s Feast at Lele, which is closed through Oct. 31. 

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