Sure, schlepping your grandkids to Hawaii to make enduring memories and forge a lasting connection across generations sounds nice and all.
But it also sounds expensive, especially since there's no way to ensure the vacation won't be ruined by sullen youngsters who'd rather stare at their electronic devices than listen to your political insights over poi at the beachside dinner that cost you a small fortune to arrange.
Luckily for families not so convinced of their capacity to enjoy one another's company, a Hawaii-based resort chain is currently running a promotion called the "Grandparent Guarantee."
For a limited time, if you book a multigenerational stay at one of the Hawaii hotels or resorts operated by the venerable Outrigger brand, and you leave the trip feeling that "connections across generations were not meaningfully strengthened," Outrigger will invite you back for "another stay, on the house."
The reservation must be made by December 31, and the first stay must happen by May 31, 2026.
The guarantee covers all Outrigger properties in Hawaii, where the company has seven hotels and resorts across the islands of Oahu, Maui, the Big Island, and Kauai. (Outrigger resorts in Thailand, Fiji, and elsewhere in the Asia-Pacific region are not part of this promotion.)
To be eligible, you must book a stay of at least 4 nights in a suite or multiroom accommodation, and you must reserve the room directly with Outrigger, either via Outrigger.com or by calling 866/256-8461.
Your party must include at least two generations, with at least one grandparent and one grandchild traveling together.
Once you're in Hawaii, Outrigger supplies several opportunities for familial bonding: lei-making, hula lessons, sailing on a catamaran, snorkeling among vibrant marine life, attending a luau, and so on.
If, at the end of all that, grandkids and grandparents look at one another and decide, Nope, these people are still duds, guests must contact an Outrigger representative by dialing 866/256-8461 to request a credit for a free return stay. (We hereby volunteer to monitor those calls for quality assurance and entertainment purposes.)
The request must be made no later than June 1, 2026, and the return stay has to happen by May 31, 2027 (blackout dates may apply).
The credit will be for the "same property, same room category, and no more than the original number of nights stayed, up to a maximum of four (4) nights," according to the offer's terms and conditions.
Obviously, the credit applies to the room rate only; all other costs, including airfare, remain the responsibility of the guest.
The promotion has other terms and conditions, but there's nothing in there that says you have to return with the grandkids. Hey, you tried.
For more information on Outrigger's Grandparent Guarantee, go to Outrigger.com.
Frommer's Hawaii 2026
Comprehensive and fully updated, Frommer’s Hawai'i covers all the major Hawaiian Islands, and takes you from world-famous beaches to secluded rain-forests to blazing hot restaurants—and everywhere in between. Frommer’s authors are expert, seasoned journalists, like Natalie Schack and Catherine Toth ...
Get the bookFrommer's Hawaii 2026
Comprehensive and fully updated, Frommer’s Hawai'i covers all the major Hawaiian Islands, and takes you from world-famous beaches to secluded rain-forests to blazing hot restaurants—and everywhere in between. Frommer’s authors are expert, seasoned journalists, like Natalie Schack and Catherine Toth ...