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

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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…

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Derek Reinhard

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