The Nostalgic Boomer Travel Trend That's Making A Comeback, Thanks To Millennials

The evolution of travel is like a fashion cycle. Processes become outdated until they are old enough to become new again. That's what we're seeing with timeshares — properties divided among a group of buyers, each getting a guaranteed window of time there every year. No bidding wars, and no Airbnb roulette.

They were popular amongst Baby Boomers, but began to lose steam with Gen X when maintenance fees rose, and commitments started to feel like a burden. Now, like your mom's vintage pair of high-waisted jeans, they're making a comeback with the younger generation. According to a 2022 American Resort Development Association (ARDA) survey, 57% of timeshare owners are millennials and Gen Z — and that reason isn't hard to find. Home ownership can feel nearly impossible to afford, but with these shared properties, a new wave of buyers feel they finally have a stake in the real estate game with a piece of vacation property they can call their own.

One Colorado owner told Forbes, "It was an appealing alternative to buying a property we'd have to spend far more money on and rent out when we weren't using it to make the numbers work." Instead of stretching their budget on a home they'd have to rent out just to break even, they now spend five weeks a year in Breckenridge — and that's enough. The industry is paying attention, and resort companies are also reimagining what this asset looks like for a generation craving innovation.

Rather than locking buyers into one property, companies like Hilton Grand Vacations and The Marriott Vacation Clubs allow customers to buy into a points system. With the Hilton, you can cash in your points for vacation experiences around the world, making solo travel budget-friendly, especially when you don't have anyone to split hotel costs with. The Marriott uses a similar system, providing guests with a portfolio of resorts to choose from.

One traveler told Skift, "Hawaii is my happy place, but the hotels there are super expensive. Because I work remotely, I want to stay for longer than a week when I travel, and it ends up being a lot cheaper using my points with Hilton Grand Vacations." Millennials now make up 37% of digital nomads, and for a generation that works from anywhere, a guaranteed home base in Hawaii or Breckenridge isn't a luxury — it's just good planning. 

For this demographic, it goes beyond just cost. Timeshare resorts come built-in with community, such as morning yoga classes, watersports, and shared amenities that make vacationing alone feel a little less lonely. The nostalgic boomer travel trend is back, but this generation hasn't just adopted it. They've made it their own.

Another way travel is shifting is in how trips get booked in the first place. Check out our feature on how young people are booking vacations through social media.