Travel | Vacations | Timeshares

I Bought into a Timeshare…Again?

Managing expectations is the secret to loving timeshare travels

Derek Reinhard
11 min readJun 8, 2023


Streetsign saying, “Wrong Way”
Photo by Kenny Eliason on Unsplash

“Show me how I can rent a canal boat in England using your timeshare plan and we will buy it.” This was the gauntlet my wife threw down for the young sales guy across the desk from us. His response caused both our jaws to drop.

You probably know the experience; someone calls up and offers you 4 days and 3 nights at a resort in a desirable location for a ridiculously low price. The only requirement is you join them for a 2-hour presentation.

My wife and I received a call offering this “opportunity” about 8 years ago. The stars seemed to have aligned to so we would say, “yes.” I had earned enough air miles to fly anywhere in the US. I had also been staying at Hilton Hotels in a previous job so I recognized the brand.

I received a call from a Hilton Grand Vacations (HGV) representative offering a long weekend stay in Florida. Another aligned star, my wife LOVES all things Disney. So, for $99, we made a January reservation for 3 nights at the HGV Sea World Resort in Orlando.

[A personal note: I am not a representative nor even an affiliate of any companies mentioned; this is simply relating our experience with Hilton Grand Vacations]

Off we go into the unknown

With airfare and lodging costs covered cheaply, we were looking at a relatively low-cost, fun time at Disney World (and a side-trip to Universal Studios for me). We had a blast! On our last day, we made our way over to the Parc Soleil resort, where the HGV sales department, was to sit through our “payment” for having a great weekend.

My wife and I laugh now at how, on the elevator ride up, we reminded ourselves to be polite as we listened to their schtick. And we rehearsed with each other, saying, “This is all very interesting, but we really aren’t timeshare people.”

Adam, a young man whom we thought didn’t look old enough to be out of high school, met us at the reception desk. He casually led us around the sales offices to a model resort room and described its features common to all the HGV resorts. We then went…



Derek Reinhard

Writes quirky life, productivity, and relationship stuff (uses the Oxford comma). Author of 3 books on GTD and a couple coloring books.