Outrigger Resorts & Hotels launches the Grandparent Guarantee to capture the growing skip-gen travel trend in Hawai‘i

Outrigger Resorts & Hotels (a privately held hospitality group headquartered in Honolulu) has announced the launch of its latest customer-centric initiative, The Grandparent Guarantee, timed to coincide with National Grandparents Day on September 7, 2025. The program is an extension of The Outrigger Promise, the brand’s broader hospitality pledge, and is specifically designed to tap into one of the fastest-growing segments of leisure tourism: skip-gen travel, where grandparents vacation with their grandchildren without the presence of parents.

The Grandparent Guarantee is straightforward yet bold in its proposition. Outrigger Resorts & Hotels promises that multigenerational families traveling together will leave Hawai‘i with stronger connections and lasting memories. If guests feel their experience fails to deliver on this promise, the company will offer a complimentary return stay of up to four nights at the same property. In an industry where guarantees are typically limited to price protection or satisfaction assurances, this initiative stands out as an emotionally charged promise centered on family bonding.

Why Outrigger Resorts & Hotels is focusing on skip-gen travel as a growth opportunity

The timing of the Grandparent Guarantee is not accidental. Multigenerational and skip-gen travel have gained momentum globally over the past decade, driven by demographic and cultural shifts. According to AARP, about one-third of U.S. grandparents have already embarked on a vacation with their grandchildren without the children’s parents present. The Family Travel Association has further emphasized that grandparents are increasingly willing to shoulder the financial responsibility for such trips, often using them as opportunities to pass on cultural traditions, values, and family history.

For Outrigger Resorts & Hotels, headquartered in Hawai‘i and with more than 75 years of experience welcoming travelers, these shifts represent a fertile growth avenue. Hawai‘i consistently ranks among the top family travel destinations in the United States, drawing millions of visitors annually. By anchoring its new guarantee to National Grandparents Day, the company is positioning itself at the intersection of cultural reverence for kūpuna (elders in Hawaiian tradition) and the market’s evolving preferences.

The kūpuna hold a special role in Hawaiian culture, serving as keepers of wisdom, tradition, and values. By explicitly connecting its marketing and service promises to this cultural foundation, Outrigger is attempting to differentiate itself from other resort operators in Hawai‘i such as Hilton Grand Vacations (NYSE: HGV), Marriott Vacations Worldwide (NYSE: VAC), and Hyatt Hotels Corporation (NYSE: H). Whereas many global hospitality brands emphasize luxury or adventure, Outrigger is leaning into the emotional resonance of family and heritage.

How does the Grandparent Guarantee work and what makes it unique in the hospitality market?

The mechanics of the Grandparent Guarantee are designed to encourage longer stays while reinforcing the brand’s positioning around family connections. To qualify, guests must book a minimum four-night stay in a suite or multi-room accommodation at one of Outrigger’s Hawai‘i properties. Eligible trips must include at least two generations, meaning a grandparent and a grandchild traveling together, without the parents necessarily present. Reservations must be made directly through Outrigger.com or by calling the company’s dedicated booking line during the promotional period from September 7 through December 31, 2025, for travel through May 31, 2026.

If families feel that their intergenerational bond has not been meaningfully strengthened during the trip, Outrigger will provide a credit for a return stay of equal length, capped at four nights, at the same property. The credit applies only to room rates, with other expenses such as airfare, taxes, fees, resort charges, and incidentals remaining the responsibility of the guest. Redemption must be made by June 1, 2027, offering families flexibility to return within a nearly two-year window.

This kind of customer promise is still rare in the hospitality sector. While some airlines and hotel chains offer service guarantees tied to timeliness or cleanliness, few hospitality brands are willing to extend a “satisfaction guarantee” rooted in something as intangible as emotional connection. By doing so, Outrigger Resorts & Hotels is not only marketing a vacation but also positioning itself as a facilitator of family legacy, shared experiences, and cross-generational bonding.

What experiences does Outrigger offer to support multigenerational bonding in Hawai‘i?

A guarantee focused on family connection requires carefully designed guest experiences, and Outrigger is leaning on its Premier Suites & Villas Collection to deliver. These accommodations are specifically crafted for families, featuring multi-bedroom layouts, expansive living spaces, full kitchens, and private lanais overlooking Hawai‘i’s coastlines. Larger groups can even reserve entire floors through the Grand Navigator Floor at Outrigger Reef Waikīkī Beach Resort, ensuring proximity and privacy in equal measure.

Beyond accommodations, the company is curating immersive activities that appeal across generations. Grandparents and grandchildren can join together in lei-making classes, participate in hula lessons, or explore the islands through snorkeling excursions and catamaran sails. Evenings bring opportunities to share cultural traditions through lūʻau celebrations or performances such as ‘Auana by Cirque du Soleil at Outrigger Waikīkī Beachcomber Hotel, experiences designed to ignite curiosity in younger travelers while evoking nostalgia in older ones.

The company is also tapping into Hawai‘i’s longstanding cultural emphasis on ‘ohana (family) and intergenerational respect. This approach provides a cultural narrative that resonates with both local communities and visitors, reinforcing Outrigger’s reputation as a steward of Hawaiian heritage in the global hospitality industry.

How does Outrigger’s move fit into broader hospitality and tourism industry trends?

The unveiling of the Grandparent Guarantee underscores the hospitality industry’s pivot toward experience-driven and purpose-driven travel. Over the past decade, consumer surveys from organizations such as the U.S. Travel Association have consistently shown that travelers increasingly value immersive cultural experiences, family togetherness, and authentic connections over purely transactional vacations.

The rise of skip-gen travel — fueled by aging baby boomers who have both the time and disposable income to invest in family experiences — has opened a lucrative niche for resort operators. The trend accelerated following the COVID-19 pandemic, when families sought to make up for lost time with loved ones after prolonged periods of isolation. Research suggests that grandparents now spend over $179 billion annually in the U.S. on goods and services for their grandchildren, with travel ranking among the top categories.

For Hawai‘i specifically, the emphasis on multigenerational travel aligns with the state’s broader tourism strategy, which seeks to promote responsible and culturally respectful experiences. By weaving Hawaiian traditions such as hula, storytelling, and the honoring of kūpuna into its resort programming, Outrigger not only differentiates itself from competitors but also appeals to travelers seeking meaningful, values-aligned vacations.

Other hospitality players are taking note of similar trends. Companies such as Marriott Vacations Worldwide have expanded their villa and timeshare offerings to capture extended families traveling together. Cruise operators, including Royal Caribbean Cruises Ltd. (NYSE: RCL) and Norwegian Cruise Line Holdings (NYSE: NCLH), have likewise invested in family-friendly cabins, kids’ clubs, and senior-friendly amenities. Outrigger’s decision to tie its offering to an emotional guarantee — ensuring that families leave with stronger bonds — represents a creative extension of this larger industry movement.

What does the Grandparent Guarantee signal about the future of travel demand in Hawai‘i?

The program’s introduction hints at Outrigger Resorts & Hotels’ long-term strategic view of Hawai‘i’s tourism market. With the state attracting more than 9 million visitors annually in pre-pandemic years, tourism has long been the cornerstone of Hawai‘i’s economy. However, the sector has been under pressure to evolve, balancing economic growth with sustainability, cultural preservation, and the shifting demographics of travelers.

By promoting skip-gen travel, Outrigger is effectively broadening its target audience beyond nuclear families and couples. This allows the brand to tap into a demographic that often books longer stays, travels outside traditional school vacation periods, and spends more per trip — all factors that can help stabilize hotel occupancy rates during off-peak seasons. Offering a guarantee of family connection also provides a hedge against the perception of Hawai‘i as an expensive or over-touristed destination, instead framing it as a place where intergenerational value can be created.

Industry observers suggest that such initiatives may encourage other Hawai‘i-based operators, including Hilton Hawaiian Village and Marriott’s Ko Olina Beach Club, to adopt similar family-focused guarantees or packages. In a competitive hospitality landscape, companies that successfully tie their offerings to both cultural authenticity and evolving consumer behavior stand to capture a larger share of high-value leisure travelers.

How might initiatives like Outrigger’s influence long-term customer loyalty and repeat visitation?

Hospitality brands increasingly view loyalty not just as a function of points or perks but as an emotional connection that drives repeat visits and long-term brand advocacy. By offering the Grandparent Guarantee, Outrigger Resorts & Hotels is effectively betting that the promise of multigenerational connection will create a powerful sense of trust and goodwill.

This approach could resonate particularly well with grandparents who see travel as an investment in family legacy rather than just a leisure purchase. For them, the guarantee functions as both reassurance and an invitation to return. Even if they claim the complimentary stay, they may ultimately generate additional revenue through dining, excursions, and extended bookings. Over time, this could create a virtuous cycle of repeat visitation, word-of-mouth referrals, and a loyal customer base.

The timing of the initiative also reflects a broader effort within Hawai‘i’s tourism industry to adapt to shifting traveler expectations. As the state continues to recover from the pandemic’s impact, hospitality operators are under pressure to balance visitor demand with community well-being and cultural preservation. Outrigger’s strategy of aligning with Hawaiian traditions of honoring kūpuna positions the company as both culturally sensitive and commercially savvy, appealing to stakeholders across the spectrum.

As multigenerational and skip-gen travel continue to expand, initiatives like Outrigger Resorts & Hotels’ Grandparent Guarantee could set a precedent for the broader hospitality sector. By offering more than just accommodations and focusing instead on emotional outcomes, the company is positioning itself for long-term relevance in a competitive market. For families seeking meaningful connections, and for industry peers looking for innovative models, Hawai‘i may soon be seen not only as a tropical escape but also as a symbol of intergenerational unity in modern travel.