In 1999 I took my family to Disney World and had no idea what I was doing.
We booked a room at a Howard Johnson’s on my grandma’s recommendation. Great call in the 1950s. Not so much in 1999. It was me, my husband, my brother-in-law and sister-in-law, and 4 kids under 10 (my son was 6, my daughter was almost 3, plus my niece and nephew), wandering into Magic Kingdom with no plan and no clue.
We didn’t know you could stay on Disney property. We didn’t know some hotels put you 10 minutes from the gates and others put you 40. We just showed up and figured it out as we went, which meant we spent money in the wrong places and missed the stuff that would’ve mattered most to a 6-year-old and a not-quite-3-year-old.
I wasn’t in the travel industry back then. I was a stay-at-home mom, and that trip was the kind of vacation you save up for and plan around for months. But even with zero industry background, I remember thinking: there has to be a better way to do this.
That thought sat with me for years. I went on to work in outpatient mental health as an office manager. The whole time, I was still the one planning every trip, still the friend everyone called before their own vacations.
The actual career change came when my husband and I moved from Long Island to Virginia and I retired. I wanted work that gave me more time for the thing I loved, which was travel. So I became an advisor. And I finally understood what that Howard Johnson’s trip had been trying to teach me the whole time: your vacation dollars are an investment in the most limited thing you have, which is time away from work.
That’s the job now. When I sit down with a family that reminds me of mine in 1999, I dig into their budget with them. I explain why staying on Disney property is worth it, or why the area you pick matters more than people think, because every dollar saved on the wrong thing is time you don’t get back.
My husband and I are grandparents now, and we still go back to Disney World, except the group’s bigger and the goal is different. It’s not about surviving the day with 4 kids under 10 anymore. It’s about getting everyone, kids and grandkids, into one villa instead of scattered across separate rooms, so the trip is as much about the conversations back at the resort as it is about the parks. That’s become my specialty: multi-generational family trips. I know what it feels like on both ends, the young family with no plan in a Howard Johnson’s, and the grandparent who just wants everyone together in the same room for a week.
If any of this sounds familiar, I’d love to talk about what your next trip could look like.
#TravelAdvisor #MultigenerationalTravel #DisneyVacation
