Launching on National Grandparents Day, the program promises that families will leave with deeper connections across generations - or receive a complimentary return stay
September 4, 2025 at 03:00 PM
September 4, 2025 at 03:00 PM EST - In honor of National Grandparents Day on September 7, OUTRIGGER Resorts & Hotels today unveiled The Grandparent Guarantee – the next bold evolution of The OUTRIGGER Promise. Rooted in Hawaiian values and designed for one of today's fastest-growing family travel movements: skip-gen vacations – where grandparents and grandchildren set out on adventures together – the pledge celebrates kūpuna (elders) and the timeless tradition of strengthening familial bonds.
With The Grandparent Guarantee, OUTRIGGER makes a heartfelt promise: guests traveling across generations will leave Hawai'i with deeper connections and memories to last a lifetime – and if not, the premier beach resort brand will invite them back for another stay, on the house.
For more than 75 years, OUTRIGGER has been welcoming 'ohana (family) from around the world to its resorts across Hawai'i. Many have gathered on its beaches, shared traditions through cultural programming and created core memories in its spacious suites and villas. That legacy of hospitality is what gives OUTRIGGER the confidence to guarantee not just an extraordinary stay, but the connections it fosters.
A New Wave of Family Vacations
Skip-gen travel has moved from niche to the mainstream in recent years. Roughly a third of grandparents have already taken a skip-gen trip (AARP) and the Family Travel Association reports that they are often footing the bill and curating vacation experiences for their loved ones. The industry cites multi-generational travel — with skip-gen as a fast-rising subset — among the world's top global travel trends.
In Hawai'i, those roots run even deeper. Hawaiian culture has long revered kūpuna as anchors of wisdom and tradition. Not to mention, Hawai'i consistently ranks among the top family travel destinations in the U.S., making it a natural stage for these meaningful journeys. The Grandparent Guarantee honors that legacy while embracing a travel trend that is redefining how families choose to spend time together today.
"In Hawai'i, kūpuna are the anchors of tradition and connection," said Sean Dee, EVP and Chief Commercial Officer at OUTRIGGER Hospitality Group. "We see that spirit reflected in the growing trend of skip-gen travel. OUTRIGGER's Grandparent Guarantee honors that role by ensuring every stay provides a setting where family bonds can deepen across generations - guaranteed."
How It Works
Signature Experiences for the Young and the Young at Heart
At OUTRIGGER Resorts & Hotels, opportunities for kūpuna and *keiki (*children) to bond are woven into each day. Loved ones might begin with lei-making or hula lessons that honor Hawaiian traditions, set sail together on a catamaran or snorkel among vibrant marine life, then share wide-eyed wonder at a lūʻau or world-class entertainment such as 'Auana by Cirque du Soleil at OUTRIGGER Waikīkī Beachcomber Hotel. These shared experiences transform a simple getaway into a legacy of discovery and laughter, cultivating a sense of place that is uniquely OUTRIGGER.
Premier Suites & Villas Collection: Curated for Memory-Making
The Grandparent Guarantee is anchored by OUTRIGGER's Premier Suites & Villas Collection, thoughtfully designed with both multi-generational gatherings and skip-gen adventures in mind. Featuring multiple bedrooms, expansive living areas, full kitchens and private lanais overlooking the Pacific, these spaces make it effortless for loved ones to come together in barefoot luxury. From the Grand Navigator Floor at OUTRIGGER Reef Waikīkī Beach Resort – where entire families can spread out across a dedicated floor under one seamless reservation – to the Royal Huakaʻi Suite at OUTRIGGER Kona Resort & Spa, where stories unfold against endless ocean views, every detail is designed to spark togetherness and shape stories that endure.
Suite stays also include exclusive access to the Voyager 47 Club Lounge, where a locally inspired breakfast starts the day and sunset toasts come with premium beverages and pūpū (light bites) for all to enjoy.
From oceanfront adventures to evenings under island skies, OUTRIGGER welcomes travelers of all ages to share their journeys on social media with #GrandparentGuarantee.
TERMS AND CONDITIONS:
To be eligible for the Grandparent Guarantee, travelers must book and stay a minimum four-night stay in a suite or multi-room accommodation at any OUTRIGGER Resort or Hotel in Hawai'i (O'ahu, Maui, Kaua'i Hawai'i Island). Bookings must be made directly through OUTRIGGER.com or by calling 1-866-256-8461 in the booking window of September 7, 2025 through December 31, 2025, for stays from September 7, 2025 to May 31, 2026. Qualifying parties must include at least two generations, with a minimum of one grandparent and one grandchild traveling together.
Following the qualifying stay, if guests feel that the Grandparent Guarantee has not been met – meaning connections across generations were not meaningfully strengthened – they must contact an OUTRIGGER representative at 1-866-256-8461 no later than June 1, 2026 to request a return-stay credit. The guest will be credited 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. Blackout dates may apply. Redemption of the credit must be used for stays completed by May 31, 2027.
The credit applies to the room rate only; all other costs – including airfare, ground transportation, taxes, fees, resort charges, incidentals and any additional expenses – remain the responsibility of the guest. This limited-time offer may only be redeemed once per qualifying booking. For more information and qualifying criteria, visit www.outrigger.com/grandparentguarantee.
Eligible properties include OUTRIGGER Reef Waikīkī Beach Resort, OUTRIGGER Waikīkī Paradise Hotel, OUTRIGGER Waikīkī Beach Resort, OUTRIGGER Waikīkī Beachcomber Hotel, OUTRIGGER Kā'anapali Beach Resort on Maui, OUTRIGGER Kona Resort & Spa on Hawai'i Island and OUTRIGGER Kaua'i Beach Resort & Spa.
For more than 75 years, OUTRIGGER has charted a journey of discovery – expanding from Hawai'i to premier resort destinations including Fiji, Mauritius, Thailand and the Maldives. The privately held hospitality company invites guests to 'Come Be Here' with authentic Signature Experiences and the OUTRIGGER DISCOVERY loyalty program – a member of the award-winning Global Hotel Alliance (GHA). OUTRIGGER's multi-branded portfolio includes OUTRIGGER Resorts, Hawaii Vacation Condos by OUTRIGGER®, The Kapalua Villas Maui and OUTRIGGER Honua Kai Resort & Spa while also managing select properties from top international hotel brands including Embassy Suites by Hilton®. Find out more at OUTRIGGER.com or visit @OUTRIGGERResorts on Facebook and Instagram.