I should have been suspicious from the start. Because the older I get — and I just turned 68 — the more I recognize that when I react rather than respond, or am impulsive rather than intentional, allowing my body to move more quickly than my brain, the situation rarely ends well.
The story begins last March. When I reserved a hotel room for a women’s conference in Des Moines, Iowa, this coming February, the booking agent asked at the end of the call if I could stay on the line to hear a marketing offer. Because the property where I had booked a room is part of a major hotel chain, my reward would be 500 points in the organization’s honors program. “Sure,” I told the agent, “I’m game.”
Apparently, I had joined the program for repeat customers back when I traveled to professional conferences once or twice a year. On my own time, I prefer to stay at AirBnB or VRBO short-term rentals because the properties are homey and private, provide a kitchen that helps save on meal costs and tend to be situated among the locals. In short, I feel less like a pampered tourist.
But pampering is precisely what this hotel chain — and all of the hotel-affiliated timeshare programs — aims to do. The marketing pitch was an enticing offer to spend a few discount-rate nights at a swanky property in Las Vegas or Florida or, my choice, New York City in exchange for a two-hour meeting about the company’s “exclusive timeshare brand.”
The pitchman on the phone asked about my travel habits, employment history and marital status. (Red flag!) Then he offered a reasonably priced deal for three days and two nights at a hotel in midtown Manhattan, but he emphasized repeatedly (another red flag) that I had to pay the $285.75 charge on the spot — that day! I also had to promise that both my husband and I would be on time for the 8:30 a.m. timeshare meeting the morning after we arrived. Otherwise, our hotel room would revert to full price, about double the promotional rate.
Some weeks later, we forked over an extra 65 bucks to convert the trip to a slightly longer four days and three nights at a property in downtown Chicago, a scenic train ride away from our home in the Twin Cities. The tactics of the hard sell at the morning meeting (“don’t be late,” the desk clerk warned when she checked us in at the hotel) harkened back to the original phone call. Not duplicitous but canny, and well rehearsed.
Buy now, pay later
From the get-go, the whole tone and tenor put me on edge, employing sales techniques I had never experienced, even on a car lot. Once we arrived at a modern, amenities-laden property a 15-minute walk from where we were staying, I had to answer a list of the identical questions the telephone salesman had asked me weeks before (marital and employment status being key).
Hotel representatives also wanted to know our top “dream vacation” spots to get away. My choice of Canada and the Netherlands may have been a clue that we weren’t their highest budget catch.


Once the Keurig machine had brewed our coffee and we’d collected mini containers of yogurt and cellophane-wrapped pound cake (the promised breakfast), the meeting began, led by a jovial salesman named Pete.
- Dressed in business casual (a jacket and necktie would show up later on the man who tried to close the sale), he ushered us into a brightly lit office with partial walls and no door, lending an air of immediacy and vibrancy given the noisy activity in the hallway.
- The persistent beat of the piped-in Muzak, loud enough that I sometimes couldn’t hear what Pete was saying, seemed designed to distract us. When I asked if he could turn the music down, he said the volume kept others from overhearing Social Security and credit card numbers when deals were getting done.
- Within minutes of sitting down, Pete asked us what type of properties we usually like to stay in. I explained our preference for short-term rentals — they accommodate my early-bird and my husband’s night-owl tendencies — and specifically mentioned Airbnb. Later, when Pete was showing us a typical timeshare suite on an upper floor of the hotel, he told us that he once discovered a video camera in the shower of an Airbnb and (“thank goodness!”) removed it before his wife used the bathroom.
- Noting that a key card is required for entrance to the elevators, Pete stressed the safety of the hotel chain’s timeshares — a selling point for the graying target market — and said only other timeshare members would be on the floor of any property we rented. Like a gated suburban community, we’d be tucked in among our own.
Throughout the exciting, emotional, enticing presentation (and it was all three), Pete flipped through digital photos of hotel-chain properties, from resorts and cruises to “glamping” sites at national parks, on a horizontal monitor embedded beneath his glass-topped desk. He said we could join the timeshare program for $80,000 — more than 20 percent of which would be due that day.

“We can’t access that kind of money on the spot,” I told him. “It would have helped to know this coming into the meeting.” He assured us the company could provide a credit card on which to finance the $17,000 down payment; we would sign a contract for the rest, plus the annual HOA fee of $2,100.
My head was spinning. “Could you give us your last name and mobile number,” I asked, “so we can talk things over this afternoon?” Pete said he carried no business cards — an odd practice for a salesman — and stressed again the act-now nature of the offer. Just like the telephone sales pitch that had gotten us to Chicago in the first place, the deal had to be done immediately. On the spot.
Nearly 90 minutes into the two-hour presentation, I learned that our assigned timeshare location would be in Florida, with options to use other company properties around the world. I had already explained to Pete that I wouldn’t spend money in a state where my transgender cousin could be charged with a felony for using a women’s bathroom and where the ACLU describes the year-old abortion ban as “near total,” with “no real exceptions for rape or incest.”
He said no other property was available that day — these being act-now, one-time offers. Then he brought in a “closer,” a trim man in a tailored suit, who consulted his iPad and said he happened to have a different Florida property for only $53,000, a considerable savings from the original quote of $80,000.
But it was Florida again, which we neither wanted nor requested. I walked out, leaving my husband to extricate himself while I waited on the sidewalk, red flags flying everywhere I turned.
Exit strategy
A timeshare sounds like a great idea, a cooperative ownership agreement with like-minded people for a property you have toured and approved. Or, so I thought, based on the arrangement my late father’s law firm had at a ski resort in Colorado.
In this case, the hotel chain wasn’t selling us a property per se. We were purchasing points for the right to stay a certain number of nights per year at any company property — 30 nights, based on our $80,000 purchase price — but we’d still be attached to this place in Florida, sight unseen.

My husband and I hadn’t realized that timeshare agreements can be notoriously hard to get out of. I learned that after a Google search led me to warning articles from AARP, a source I trust because they target scams that target seniors. A few days later, searching for the replay of a WNBA game on YouTube, I was stopped cold by an ad from Wesley Financial Group about “timeshare lies.” Apparently, my browsing history had led them to me.
Dubbing itself “the most proven and reviewed timeshare exit company” — CEO Chuck McDowell used to be a timeshare salesman — Wesley employed an attractive young actress to ask whether any of these sales tactics had been used in our timeshare pitch:
1. “Your maintenance fees will never go up.” Yes, Pete had told us that. On average, said the Wesley spokeswoman, they go up 4 percent a year.
2. “This is a financial investment.” We’d heard that, too. But real estate investments pay off based on supply and demand, “and the supply [of timeshares] is always high because of the massive marketing machine that is the timeshare industry,” the Wesley woman said.
3. “Your obligations will die when you pass away.” Actually, Pete had suggested the opposite, saying we could transfer the Florida property and the timeshare points to our two grown sons once we became too infirm to travel. Regardless, according to Wesley Financial Group, “most agreements are in perpetuity.”
After sitting through the mandatory meeting in Chicago, I recognized that a hotel- or resort-based timeshare — offered by Marriott, Disney, Wyndham, Hilton and others — could be ideal for people who travel more often than I do, who want luxurious accommodations where they are separated and safe, and who don’t let political leanings or social issues dictate their destinations.
That isn’t me. In hindsight, I am grateful to have walked away a little wiser and a whole lot less naive, and didn’t fork over $80,000 to remind myself of who I really am.


Thanks, Amy, for this insightful article and for standing up for your principles. Yeah, Florida, stinko!
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