family planning a vacation

What Does A Kid Actually Remember About a $5,000 Vacation

August 26, 20264 min read

Here is a question I like asking people my age: What did you get for Christmas in 1989? Most of us have no idea.

There may have been a bicycle, a Nintendo game, a jacket we were convinced would change our social life, or some piece of technology that is now sitting in a landfill with several million Walkmans. Whatever it was, the object usually disappeared from memory long before Christmas itself did.

We remember who was there. We remember the house. We remember a tradition. We remember somebody saying something that became family folklore. We remember the year the tree fell over, or the dog ate something, or Dad attempted a repair that should have involved a professional. Vacations work similarly.

A family can spend $5,000 on a trip without much difficulty. Depending on airfare, lodging, food, and attractions, that number can disappear surprisingly fast. So what is the family actually buying?

Technically, it is buying nights, meals, transportation, and access. Emotionally, I think the family is buying the possibility of memory.

Cornell psychologist Thomas Gilovich has studied the difference between spending on possessions and spending on experiences for decades. Cornell has summarized that research by noting that experiential purchases are often remembered, talked about, and woven into our identities more readily than material purchases. Cornell's research on experiences and happiness points to social connection and storytelling as two of the reasons experiences can retain psychological value after the transaction is long over.

Gilovich offered another useful observation in a 2026 Cornell piece about memorable adventures: much of the pleasure of an experience comes later, when we look back on it. Memory is not a perfect recording. It is a story we keep editing. That sounds exactly like family vacation history to me. The fish gets bigger every year. The waves get rougher. The hike gets longer. The time Dad got lost becomes funnier after everyone has forgotten how irritated they were in the moment. Families turn experiences into stories, and stories become part of the family itself.

This is where I think the definition of luxury gets interesting.

Luxury does not have to mean that every surface is expensive. It does not have to mean that a family must spend five figures before the trip qualifies as special. Sometimes luxury is having a beautiful place to wake up, enough room to breathe, something genuinely interesting outside the door, and the time to enjoy it.

Can a family have a trip that feels luxurious for under $5,000? Depending on the travel party, season, and choices, I think the answer should be yes. That does not mean every Victory Springs stay will fit every budget, and it is not a pricing promise. It is a design objective worth pursuing: create experiences with emotional richness that is not dependent on conspicuous spending.

That is one reason I am excited about beginning Phase One with Victory Camp as part of the broader Victory Springs development. The concept allows us to explore a more accessible expression of the property, still rooted in nature, experience, and intentional hospitality, without assuming that meaningful family travel has to become a financial endurance test.

A recent MSN feature about Victory Springs and family travel made a related observation: the moments families often remember are not necessarily the most elaborate amenities. They are the porch conversations, the meal, the morning view, the grandparent who could participate, the children who went outside and found something to do.

Those examples are useful because they reveal something developers cannot fully control: we cannot manufacture a family's favorite memory. We can manufacture a waterslide. We can install a television. We can buy furniture. We can schedule activities. But the thing a child remembers twenty years later may be the turtle they found underneath a rock while walking back from something we thought was the main event.

The work of hospitality is therefore a little humbling. Our job is not to dictate the memory. It is to create fertile ground for one.

That can mean designing places that encourage interaction rather than isolation. It can mean giving children enough freedom to explore. It can mean preserving the strange tree instead of replacing it with a perfect ornamental one. It can mean creating a comfortable outdoor place where nobody feels rushed to leave.

And it can mean remembering that the guest is not necessarily evaluating the property the way the developer does. We may be proud of the expensive feature. The child may remember the salamander.

If you ask somebody what they received for Christmas thirty-seven years ago, you will probably get a blank stare. Ask about the family trip where Grandpa fell out of the canoe, and suddenly you have a twenty-minute story. Experiences have a way of surviving their receipts. That is the kind of value I want us thinking about as we build Victory Springs. Not simply what somebody paid for the vacation, but what they still possess after the vacation is over.

Jeramie Worley

Jeramie Worley

Jeramie Worley is the Operating Partner of Victory Springs Capital LP, a Fund Manager, Commercial Broker, and Lifestyle Asset Specialist focused on experiential retreat development. With over two decades of experience in short-term rental and resort real estate, he has brokered more than $2 billion in hospitality-related transactions across multiple markets. Author of "Myth's, Management & Mastery of Vacation Rentals," Jeramie has led the development, acquisition, and structuring of experiential real estate projects throughout the Branson and Table Rock Lake markets. Featured in The Wall Street Journal article “The Short-Term Rental Market Is Coming of Age” for his insights on the evolution of the industry and the impact of millennial-driven demand. His work centers on bridging traditional real estate development with modern, experience-driven hospitality through scalable, investor-aligned projects.

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