Family Travel to Hawaii


Have you booked a multi generational family trip lately? Chances are you have, and you’re not alone. “The field is growing exponentially,” says Kimberly Wilson Wetty of Valerie Wilson Travel in New York City. “It’s the fastest-growing segment of the travel industry.”

Wetty raves about children’s programs at Four Seasons Resorts and Ritz-Carlton, and is especially impressed with those at Rosewood Hotels & Resorts in the Caribbean. She also cites Holland America’s four- and five-person Cabin Suites as a great idea for multigenerational cruise travel.

Wetty also says that “Hawaii is a wonderful destination for multigenerational family trips,” citing the Big Island’s beaches, golf, and volcano, Maui’s shopping and dolphin-swim excursions, and Oahu’s Pearl Harbor and North Shore.
Here are three Hawaiian properties worth considering for your next multigenerational


At the elegant Princeville Resort Hotel ( in Kauai, Guest Services Manager June Sundberg (808-826-2233) handles all VIP arrangements, from stocking favorite foods and flowers to conducting daily morning activity briefings. General Manager Kelly Hoen (808-826-2221) is also available to VIPs. Parents should stay in the 1,800-square-foot Presidential Suite ($3,900 per night), while grandparents, older children and their spouses and kids can stay in the next 10 rooms down the hall. The Presidential Suite features a full kitchen with Sub-Zero refrigerator and available butler service. The 1,200-square-foot Executive Suites are another option, at $2,000 per night. VIPs can request a private luau on the beach, a buyout of the hotel’s regularly scheduled luau, and beach dinners in a private cabana at the water’s edge, in view of magnificent “Bali Hai” (Mt. Makana).

For private helicopter tours, contact Rich Johnson at Heli USA (808-826-6591;

Princeville guests receive discounts at the award-winning Prince Golf Course and on fitness and spa services. The spa director is Melody Jones (808-826-5032). Book an oceanside massage (be sure to request Marion McHenry). The hotel’s secret weapon is Dora Swain, a former employee who teaches Hawaiian cultural activities such as quilting and lei making; she also “talks story” about Hawaiian history and traditions.
Another unique experience the whole family can enjoy: Request Trevor Cabell, who takes guests sailing on an authentic outrigger canoe that he built himself.

Two top restaurants nearby are Gaylord’s at Kilohana Plantation, and Postcards, which serves gourmet vegetarian food. Funky shopping is in nearby Hanalei.
For departing guests, the hotel caters “food for flight” and transports it to Lihue Airport, which allows private jets. For a chauffeur, contact Brett Deblin at Northshore Limousine Service (808-634-7260).

Why stay in a hotel when you can command a complete residence for the price of a single room? Maui’s luxurious Kaanapali Alii condominium ( is a home-away-from-home with complete hotel and concierge services. VIPs should request the “Premier” two-bedroom oceanview units, outfitted with Sub-Zero appliances and oversized lanais.

Insider tip: The Alii’s poolside gas barbecues and grocery delivery are ideal for informal family picnics.

General Manager Mark Altier (808-667-1400, ext. 425) and Luxury Concierge Carmela Mahon (866-661-2544) handle VIP arrangements. (Carmela recently assisted a guest with booking the Gemini sailing yacht for a half-day snorkel sail for $2,500). For a nanny, contact Christine Taylor, owner of The Nanny
Collection (808-667-5777). For a chauffeur, contact office manager Ilima at Kapalua Executive (808-669-2300).

Alii guests receive signing privileges at all restaurants and bars at the adjacent Marriott, Westin, and Sheraton properties in the Kaanapali resort area, as well as at the golf course and Lahaina’s award-winning David Paul’s restaurant where Mahon can arrange private dinners and parties in a room that accommodates eight. For a lavish private luau, call manager Randall Baybayan at the intimate, gourmet Feast at Lele (808-667-5353); he’s sold numerous buyouts.

From the Alii, more than 50 great restaurants (such as Hula Grill) and shops are a two-minute walk away in Whalers Village. Guests also receive signing privileges at the Westin and Hyatt’s Spa Moana, whose spa director is Claudia Wattenberg (808-667-4427). Request the decadent chocolate-macadamia-nut Ka’anapali Coffee Scrub.

The Alii is just steps from Kaanapali Beach, so the whole family can swim, surf, snorkel, or simply relax.

In Molokai, the locals say, “Molokai mo bettah” (more better), and with the delicious abundance of “nothing” as its main attraction, it’s the “Seinfeld” of islands. “Molokai is known for its feeling of ohana (family),” says Teri Waros, general manager of The Lodge at Molokai Ranch (; 808-660-2823). Waros handles all VIP requests; she recommends that VIPs and their families stay in the eight-room Lodge Cottages—each with two king-size beds—located on its 65,000 secluded acres. Many buy out the entire Lodge, with its 22 rooms, for corporate retreats or family reunions.


What sets the Lodge apart is its homespun charm; Waros has an army of extended family and friends who take guests fishing, flower picking, surfing, star-gazing, and more. Families can dine together privately on the gardenview lanai or in the Lokahi Room. Instead of a spa, there’s a “Healing Hui” (co-op) of healers, masseuses and acupuncturists. Family members can bond by horseback riding (and rounding up cattle) in a full rodeo arena, clay shooting, archery, in-tandem kayaking,
snorkeling, mountain biking, and boogie boarding. Golf is just 10 minutes away at the easygoing Kaluakoi Golf Course.

Contact Tim Forsberg at Molokai Fish and Dive (808-553-5926); the whole family should experience the famous and thrilling Molokai Mule Ride into Kalaupapa, the former leper colony.  

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