Hollywood's Hot Hawaiian Getaways: An Island-by-Island Guide

6:40 AM 6/20/2017

by Kathryn Romeyn

Larry Ellison's new Lanai "experience," zip-lining the Big Island with Justin Bieber and a VIP Spago package at June's Maui Film Festival give industry insiders new reasons to explore beyond the Four Seasons pool.

Hawaii Kohanaiki Home - Publicity - H 2017
Courtesy of Murphy O’Brien Public Relations

During the summer and holidays, a five-and-a-half-hour flight from L.A. often means Hawaii for Hollywood's bold-faced crowd. "It's the same as going to New York for the weekend, except you end up in paradise," says Don Cheadle's partner, actress-designer Bridgid Coulter. "You're in tune with the land, eating the fruit, catching the fish." Hawaii is currently trending even more than usual, thanks to its many new indulgences and lack of Zika. "Hawaii is huge this year," says Jaclyn Sienna India of travel company Sienna Charles, which caters to high-net-worth clients. (All major carriers go, but passengers who don't fly private might want to check out Hawaiian Airline's tech-advanced A321neo planes, rolling out later this year. Its JFK- and SFO-to-Honolulu routes just debuted a new cabin, with lie-flat leather seats and menus by Top Chef star Sheldon Simeon.)

Everybody loves the Aloha State: Fox Television Group co-chair and CEO Dana Walden vacations with Fox casting exec Sharon Klein and NBC Entertainment president Jennifer Salke; Bob Iger hits Aulani, a Disney Resort & Spa at Ko Olina on Oahu, that island that J.J. Abrams also likes; Margot Robbie has enjoyed Kauai; and Usher paddle-boarded in Kihei, Maui, last month. In 2016, Woody Harrelson applied to open — and was denied — a medical marijuana dispensary on Maui. Last year, Greg Burns — partner at Elite Pacific Properties, whose clients include award-winning directors — helped an A-list actor buy his father a $4 million condo and has seen a client's parrot board a Gulfstream V as the sole passenger.

Property taxes in Hawaii, coincidentally, are among the lowest in the country, while tax credits and incentives also have boosted Hawaii's appeal as a filming destination. "The crews are great and we have so many different looks: jungle, resorts and even a downtown New York," says Snatched director Jonathan Levine, who shot on Oahu. Actress Elizabeth Mitchell first discovered the islands when filming Lost, and says, “I’m captivated by the place and the people, but most of all Hawaiian nights — you’ve never felt a breeze so soft or seen a moon so bright and big. It doesn’t feel real.” Adds The Descendants helmer Alexander Payne: "It's great to be on the remotest significant landmass on Earth. You're out in the middle of the Pacific Ocean." The insider's guide to the five islands that Hollywood flocks to:



  • Hawaii

    The allure of the Big Island, where Roseanne Barr has a macadamia nut farm and visitors include Nicolas Cage and Paul Allen, is a one-of-a-kind landscape, says Coulter: "The lava meets the ocean. It's a growing island in front of your eyes." Says Sienna India, “It’s definitely the most diverse in terms of the landscape — it’ll be green, then turn into ocean, and then red from the desert.” Snatched location manager Janice Polley adds that she dreams of filming something at Black Sand Beach and areas around Mauna Kea, which she calls spectacular.

    The largest island (with far fewer people than Oahu) is always sunny, says Burns, and home to private gated resort communities Hualalai and Kukio, where stars "can walk through the front door of their house within 10 to 15 minutes of landing [their] private plane from Burbank," says Burns, adding that homes in this “ultimate sunbathing haven” with 10 climate zones go for upward of $30 million, lately to tech titans.

    Visitors can embrace the surroundings with KapohoKine Adventures. Owner Tony DeLellis acted as a 24/7 concierge for Justin Bieber's six days in Hawaii last July for $400,000, plus $50,000 for the private jet. "We kept his visit so discreet that by the time anybody knew it, he was gone," says DeLellis, who prepared a fully stocked bungalow and three vehicles with less than an hour's notice. The itinerary included helicopter flights over the volcano, ATVs, manta ray snorkeling and a private zip line trip with a waterfall swim, "clothing optional," he adds. Shakira and Chris Martin and his kids also have zip lined. "Apple even carved her name into the wooden Line 8 receiving platform," says DeLellis.

    Outdoorsy types also can check out the brand-new Extraordinary Experience package, a $39,500 overnight for up to four people (available through 2017) at Four Seasons Hualalai, adjacent to Hualalai residences, which has hosted Beyonce and Jay Z, tech mogul Michael Dell and LeBron James, and is debuting a multimillion-dollar renovation of its Canoe Club this fall. The package includes a helicopter ride over the Kohala Mountains and a visit to the lava flow of the world's most active volcano — led by a leading volcanologist — followed by a stay at the Four Seasons Rainforest Cottage Hideaway featuring live Hawaiian music, a chef-prepared meal and a private beach for snorkeling and mimosas the next day.

    At the Hilton Waikoloa Village's Kamuela Provision Company, for $895 (for two), Big Island dwellers can dine on a new chef's table feast in a private cliffside cabana that showcases all-Hawaiian ingredients (Kona coffee, Kauai prawns and Keahole lobster). Or, do like Cheadle and family and head to the 450-acre private resort community of Kohanaiki's recently debuted 67,000-square-foot Clubhouse, where Coulter says the "best, fresh and simple" poke bowl is not on the menu. The clubhouse — equipped with a spa, secret cigar room, movie theater, bowling alley, wine lockers and an art gallery — can be accessed only by buying a home (prices start at $3 million and exceed $22 million) and a $150,000 membership, plus $25,000 annual dues.

    Coulter just finished designing a $5.7 million home for the exclusive community. Colors at dusk inspired her concept, which includes custom furniture, a copper roof, a two-bedroom guest hale and outdoor shower (“you never shower inside in Hawaii”). 

  • Kauai

    Kauai is the most holistically minded of the islands, attracting Robbie, Alicia Keys and Mark Zuckerberg, who paid more than $100 million for his 700-acre property and whose mile-long wall, blocked beach access and multiple lawsuits aiming to clarify boundaries provoked local neighbors to call him the "face of neocolonialism." (He later dropped the suits and wrote an apologetic op-ed in the local paper.) Kauai draws the Malibu "cool kids," says celebrity wellness guru Rainbeau Mars, who in July hosts a yoga retreat on the island in a private Indian mansion surrounded by the jungle. "Kauai takes away the glitziness. When I'm at a restaurant, Sacha Baron Cohen [might be] sitting next to me, or The Eagles walk in, chill and relaxed. You're running into Lisa Bonet, [wife of] Jason Momoa, who's from there." Mars adds that stars who visit don't hashtag or geotag Kauai to keep it paparazzi-free and secret. ("We say, 'Send people to Maui.' ")

    Hawaii native and Hollywood power hairstylist (Lily Collins, Bella Hadid) Jen Atkin is obsessed with the beaches near the low-key Hanalei Bay, which is where Julia Roberts, Ben Stiller, Pierce Brosnan (who hangs out at local bar Tahiti Nui) and Apple's Jony Ive have homes. “It’s a very, very high density of celebrities in that area, and certainly nobody cares who you are,” says Burns, adding properties go for as much as $70 million. For paparazz,i the one-hour drive from the airport is a deterrent, ensuring valuable privacy.

    Hollywood visitors flock to St. Regis Princeville's presidential suite ($7,100 a night), where George Clooney stayed while filming The Descendants, and Keys, Ben Affleck, Taylor Schilling and many CAA agents also regularly guest. "Princeville is one of the most quintessential Hawaiiana backdrops," says Burns. "The St. Regis is epic." This summer, the resort is debuting a $9,500 secluded outdoor dinner for two, paired with Dom Perignon vintages (the rarest is from 1969, for an additional $8,800).

    For a megahit of natural beauty, Live Nation Production's president of film and television, Heather Parry, says that Kauai (which has hosted more than 120 movies) "has the best hikes and the beautiful Secret Beach," not to mention barefoot walks to waterfalls on the Na Pali Coast and dips in the Queen's Bath rock tide pool. For local treats, actress and clean-beauty entrepreneur Shiva Rose's go-tos are Jo2 for local farm-to-table cuisine, and the farmer’s market for mangos, avocados and goat cheese.

  • Lanai

    Lanai, considered to be the most elite among the islands — Rupert Murdoch owns a residence in Manele Bay — has drawn Tom Cruise, Will Smith, Oprah Winfrey and Sigourney Weaver to its private shores, 98 percent of which were purchased by tech billionaire Larry Ellison (father of Megan and David) for $300 million in 2012. His Four Seasons Resort Lanai, which opened in 2016, is "the manifestation of the Fantasy Island concept," says international luxury hotel and resort designer and TAL Studio founder-owner Todd-Avery Lenahan. "The entire island is your resort." Top suites in the $20,000-a-night range consistently sell out, says Sienna India. "Everything is super bespoke." (Its wellness Lodge at Koele opens next year — all-inclusive rates start at around $1,500 — and will offer cliff-view yoga, a new Western-with-a-wellness-focus menu by Nobu, 10 private spa suite hales with plunge pools and the Lawrence J. Ellison sculpture garden, boasting "monumental new commissions" by Jeff Koons and Frank Gehry, says Lenahan.) Adds Motion Picture & Television Fund CEO Ken Scherer: "Seldom is the reality of a resort actually greater than the hype," while Paramount Television and Digital Entertainment president Amy Powell says the staff welcomes her like family each time she arrives. UTA partner Jason Heyman recalls swimming with his kids in front of the hotel: "Suddenly, about 20 dolphins appeared and swam with us for a half-hour. It was wild and amazing, and I'm sure how Hawaii felt in years past."

    With Ellison having leased a lounge dedicated to his resort at Honolulu International Airport, visitors can now get the "experience" from the moment they disembark, says Lenahan (if they didn't fly directly into Lanai, where during high season, the airport is just a line of private jets). "With [this] enclave of complete civility, we're able to anticipate you" with check-in and bookings, "so by the time you arrive, you skip all that and are taken directly to your room."

    Each is outfitted in teak, rosewood and Nepalese lokta paper: "We spent on each unit what most new five-star hotels spend on five," says the designer. Guests have access to the local-ingredient-­sourced Hawanawana Spa and Nobu, where a private sushi cooking class with the executive chef costs $500 per person, plus a $1,000 private room fee. If Nobu Matsuhisa and his team are flown in, the fee climbs to $50,000.

    Hawaii Yachts and Global Ocean Club charters begin at $17,500 per day and include such add-ons as accompaniment by Bruno Mars' guitarist uncle. Guests are given something sturdy to drive to the Garden of the Gods ("this extraordinary area with amazing geology," says Lenahan) or maybe a Tesla or Mercedes for road trips. And come winter, Lenahan says, “there is a completely over-the-top experience that will put guests in the position to have access to the ocean that they have never before experienced,” something only scientists have done (hint: it's a submarine). Accordingly, he says the price will be “commensurate with its value in your life as a really profound once-in-a-lifetime experience.” "When you're on Lanai, it's very democratizing," says Lenahan. "You can be at the pool and see Mr. Ellison reading, and in another chair is an Academy Award winner" — with zero paparazzi.

  • Maui

    Part-time residents Clint Eastwood and Oprah Winfrey (who owns two large properties) may consider Maui the best of all the islands squished into one, counting among its visitors Steven Levitan and Jude Law. The upscale Wailea area is most in-demand: Billionaire Peter Thiel, Jim Carrey, Alice Cooper and Steven Tyler (who leads drum circles at Makena's nude Little Beach) own properties valued at $15 million to $50 million. A top pick for non-residents, such as Live Nation Productions' Heather Parry, is Four Seasons Resort Maui at Wailea, where Kanye West and Steve Tisch have been guests. Cabanas are decked out in Missoni fabrics, and there's a Spago nearby and an "exceptional" spa, says Sienna India. Adds Parry: "They have the best masseuse ever — Carrie."

    From June 21 to 25, the 18th annual Maui Film Festival in West Maui, where Viola Davis, Bryan Cranston and Brie Larson have been honored (this year, up-and-comer Karen Gillan of the upcoming Jumanji: Welcome to the Jungle receives the Rising Star Award), will take place. "People always comment on how the scents and vibes of Maui fill the air at the festival," says founder Barry Rivers, whose fondest memories include Eastwood and his wife carrying their own beach chairs up the slope at the outdoor Celestial Cinema. This year, the Cinema kicks off with Salma Hayek’s Beatriz at Dinner. The top VIP festival pass, Infinity Sapphire Circle, goes for $7,000 and is needed for access to the fest's signature Spago event. Rivers says attendees explore "the Haleakala Crater, Hana, the Pacific — or negotiate their next deal by the pool over cocktails and farm- and sea-to-table dining." One PR exec notes that filmmakers tend to work through the festival, while stars relax and enjoy Wailea.

    West Maui, which has been likened to Laguna Beach and comprises Ka'anapali and Lahaina — homes range from $4 million to $15 million — also offers such power-dining venues as Da Kitchen in Wailea as well as adventure, courtesy of Andaz Maui at Wailea Resort (Rashida Jones and Kendrick Lamar have stayed here). Its recently launched Luxploration package includes such options as a chef's table meal, private ukulele and surf lessons and a helicopter tour of Molokai (from $4,995 a night, including a villa). Meanwhile, Fairmont Kea Lani, a go-to for Kate Hudson, offers customized outings with Satisfaction Sailing Yacht charters and Maverick Helicopters, which might include a flight to organic Hana Ranch on the island's eastern shore to forage for a four-course meal. It also provides guests with luxe reproductions of 1957 Porsche 356 Speedster convertibles. Or “you can ride your beach cruiser to Fleetwood’s [owned by resident Mick Fleetwood] for a little concert, have some drinks, then ride home,” says Burns of Lahaina.

    With a car, one can go off the beaten path en route to or from Hana. The Seven Sacred Pools hike has been equated with scenes in Avatar, while "the Na'ili'ili Haele hike off Hana Highway has gotten a little touristy but is still spectacular, with hidden waterfalls and thick bamboo jungle," says Famous in Love's Perrey Reeves. "I'm a big fan of Hana," concurs Payne. "People stay on the other side of the island and drive to Hana and turn around, but I recommend making it a destination. You can rent an Airbnb or VRBO."

    The old plantation turned hippie enclave of Paia has attracted Owen Wilson (a devotee of Mama's Fish House), Willie Nelson (who plays surprise sets at Charley's Restaurant) and Harrelson, who has called Maui "heaven. A year could pass and you wouldn't notice. Kitesurfing, soccer, living off the grid, eating fruit from your trees." With The Agency's David Solomon, Burns is about to list NBA legend Don Nelson's former 1-acre oceanfront compound home, which several stars have toured, for $7 million. In September, he and Million Dollar Listing's James Harris will list a rare architectural masterpiece on the slopes of Haleakala.

  • Oahu

    Oahu — Barack Obama's childhood home and the occasional residence of Brian Grazer and Dwayne Johnson — also has hosted Iger, Will Smith, Emma Stone, Amy Adams and Justin Timberlake. The Pacific Beach Hotel's $115 million reimagining is transforming the iconic Waikiki Beach property into Alohilani Resort Waikiki Beach (the presidential suite costs $979 a night) for a fall opening and will feature a pair of restaurants from Iron Chef Masaharu Morimoto.

    The Ritz Carlton Residences, Waikiki Beach claims the only four-bedroom suite in Waikiki (up to $12,000 a night) and the exclusive 10-seat omakase restaurant by Tokyo’s acclaimed sushi chef Keiji Nakazawa ($300/person excluding beverages). “Old Hollywood loves that Waikiki/Kahala area because you wake up and see Diamond Head as your backdrop — that postcard view in front of your windows every day,” says Burns.

    The Obamas and Zuckerberg have checked out Surfjack Hotel & Swim Club (room rates go up to $500), which recently opened and has "a lot of experiential takeaways," such as a music series, says Christian Schulz, co-founder of L.A. design firm Studio Collective (projects include The Bungalow Santa Monica). After the former POTUS and FLOTUS dined at its Mahina & Sun's restaurant from acclaimed chef Ed Kenney and ordered a Grey Goose martini — shaken with extra olives — the Presidential Martini ($14) was added to the menu.

    In Honolulu's Ward Village community, a new 36th-floor penthouse is on the market for $36 million and boasts more than 10,000 square feet of interiors and a private rooftop infinity pool. Owners can order room service from Nobu Honolulu on the ground floor. "A lot of my clients or their money managers are inquiring," says Burns. "The pool pours over the top of the building — going in it is nuts."

    The 2016 opening of Four Seasons Resort Oahu at Ko Olina brought attention to the west side of the island, which marketing director Nelson Hilton says is gaining prominence in the film industry, with Marvel filming down the road at the old Naval airport Kalaeloa. The Snatched crew, including Amy Schumer, enjoyed the pool and private sections during shooting. Hilton admits that Kourtney Kardashian's spring visit challenged discretion: "It's obvious when you have bodyguards surrounding you." The reality star stayed in the 17th floor's three-bedroom penthouse suite ($18,000 a night), where, from the roof, one can watch whales jumping.

    Enjoying a surge is the North Shore, a sleepy surf town known for having some of the best swells on the planet and where sports stars and tech players are buying oceanfront estates for $3 million to $15 million. “I find a lot of our friends in the entertainment industry are drawn to the North Shore," with its "horses on the side of the road, acres of lush grass, rolling hillsides and crystal clear blue water with shell-lined shores,” says Oleema Miller, creative director and co-founder of MIKOH, which Jessica Alba wears on her Hawaiian vacations. Celine, Chanel and numerous restaurants are just one hour away in Waikiki, but she’s usually on the sand at Ehukai: “The stretch of beach is incredible — houses from Ke Iki beach to Sunset Beach are all stunning.” 

    A popular elite venue for weddings, wellness retreats and private dinners is Sunset Ranch Hawaii, which has hosted several films, castmembers from Hawaii Five-0, Jack Johnson and most recently Hailey Baldwin. With its helipad, the 27-acre property gets guests making the hop from other islands.

    Burns has rented to Bradley Cooper (Aloha); rentals now hit $10,000 a night. Grazer surfs the Banzai Pipeline, and Hawaii Five-O's Scott Caan grabs takeout with his family at Waialua Bakery or Storto's Deli for a beach day, which includes a visit to the tide pools at Shark's Cove and drinks at Haleiwa Joe's — "the jam," says Caan. He also likes Pupukea Grill for "some of the best food on the island." For cold coconuts and local treats, stop at the fruit stands at Kahuku; insiders also adore Hamachi Ponzu at Banzai Sushi and Elephant Thai, a food truck across from Shark's Cove. Payne's favorite lunch in Hawaii is the all-you-can-eat vegetarian buffet at ISKCON Hare Krishna Temple near Honolulu. "It's exquisitely clean food in a tranquil spot," the director says. "A friend turned me on to it."