Part 2: The Sweet Spot — The Early Years

To be fair, the beginning of our timeshare journey was actually wonderful.

We spent years vacationing in the White Mountains of New Hampshire. Sometimes for weekends, sometimes for a full week. We built memories with every trip—mini golf, train rides, shopping for ornaments at the Christmas Loft, even meeting Santa one year.

As the kids grew, we branched out. Orlando became our next adventure—swimming with dolphins, lazy days at the pool, Cocoa Beach, Discovery Cove. The timeshare gave us the push we needed to take vacations, and while planning was sometimes stressful, we never regretted going.

New Hampshire became our home away from home. Eventually, we returned to Orlando when our teenagers were struggling through some difficult years. We hoped a week away would help us all reset. And it did—long pool days, local shops, and nightly family dinners.

But truthfully, the cracks had already started to show. What we were sold—flexibility, availability, and easy booking—quickly unraveled. Those “early booking privileges” we were promised? They never materialized. Resorts we wanted were often unavailable, even when we tried to plan far in advance. Instead of feeling like valued members of a travel club, we became just another number in an overcrowded system.

Still, we pushed forward, clinging to the vacations that did work out. And that next Orlando trip felt like it might be one of our best yet—until the dreaded “owner update.”

For years, we believed the timeshare was one of our best decisions. But behind the happy memories, the cracks were already beginning to show.