Experiential Vacations: Curating Connection and Discovery

What Resorts Are Doing – the How and the Why

Here’s what’s happening: vacationers today aren’t just booking beds—they’re craving moments. According to ARDA’s latest white paper, the average new timeshare owner is 39 years old, and 57% are Millennials or Gen Z. That shift means this demographic comes hooked on personalization, transparency, and planning trips while still on their last vacation—60% have already reserved their next getaway before leaving home.

At Resort Trades, we’ve been covering this trend closely, including our recent feature on ARDA’s timeshare industry report, which highlights how younger owners and today’s travel-savvy families are driving the call for more flexibility and memorable experiences (Resort Trades talks about ARDA’s timeshare industry report).

Meanwhile, experiential travel itself is booming everywhere. Whether it’s walking through a butterfly garden, sitting down for vineyard dinners, joining an art tour, or taking a music lesson, guests are leaning into opportunities that let them learn, taste, and connect in ways they never could by simply lounging poolside. One recent Resort Trades article put it best: experiential travel “emphasizes personal connections resulting in deeper, authentic, and meaningful experiences that leave a positive impact.”

So yes—when you invite your peers around, it’s no longer about another day at the pool. It’s about becoming part of those stories guests tell friends and family for years.

Balancing Familiarity with Exploration

Think about Travel + Leisure Co. (formerly Wyndham Destinations). On one hand, you’ve got cozy, trusted brands where owners know exactly what to expect. On the other, their massive portfolio unlocks fresh horizons. That balance—home comfort plus discovery—is what modern travelers crave. They want to revisit favorites, but they also want to check something off their “someday” list. Travel + Leisure’s wide net across Club Wyndham, WorldMark, Shell Vacations, and Margaritaville Vacation Club makes it possible to do both.

Personalization: Not Just a Sticker on the Door

Thanks to smarter tech, AI, and data, resorts are starting to get personal even before check-in. The ARDA study highlights how matching preferences—like suggesting a local café to a coffee lover or showcasing a spa preview via augmented reality —builds trust and connection, not just sales. (Augmented reality, or AR, is technology that layers digital visuals or information over the real-world environment. For example, a resort might use an augmented reality preview — say, through a mobile app — to let a guest virtually walk through the spa or view a treatment room before booking.) Personalization today isn’t about room upgrades alone; it’s about listening to what guests love and surprising them with thoughtful touches that make the stay memorable.

Going Beyond Pools and Theme Parks

Here’s the real shift: guests want hands-on experiences. A study from Arival.travel confirms consumers aged 18–54 are prioritizing culinary classes, local-maker tours, and cultural deep-dives over traditional checkbox travel. Add to that the Adventure Travel Trade Association’s insight: immersive travel drives revenue, even as mass tourism stabilizes.

And timeshare resorts are answering.

• Hilton Grand Vacations has embraced intimate entertainment through “HGV Live!”—bringing names like LeAnn Rimes and Carly Pearce to private resort stages so members feel like insiders, not just spectators.
• Holiday Inn Club Vacations has leaned into VIP Experiences, offering curated moments like hot-air balloon rides, scenic excursions to landmarks such as the Hoover Dam, and curated tastings. These packages go beyond “vacations” to become stories families retell.

Bring This Home to Your Property

• For developers: ask yourselves—what’s your “butterfly garden moment”? Maybe it’s a night under the stars with a local musician, a hands-on cooking class, or an authentic neighborhood art walk.
• Marketers: tell stories of connection—sell the memory, not just the lodging.
• Resort managers: make it simple. Let guests book that sunrise yoga session, vineyard tasting, or artist workshop through your app or at the front desk. The easier you make it, the more likely they are to say yes.

Final Thoughts

The timeshare industry is shifting. It’s no longer about selling a week—you’re selling connection, growth, and emotion. As ARDA pointed out, trust and transparent flexibility are the new expectations. The brands stepping up—from VIP dinners to concierge-curated adventures—are the ones crafting those unforgettable moments.