How Not to Buy a Timeshare

Very early in my first marriage—I’m talking four or five days—I lay on a lounge chair on the white, powdery sand of an island paradise and took stock of my problems. First off, in that short time I’d already managed to lose both a piece of precious heirloom jewelry that my new mother-in-law had given me and also my new husband’s lucky Mets cap, which I’d left at a bar one island over. He’d taken both of these losses hard, and he’d felt that the missing jewelry had to be reported at once—long-distance and from the front desk—to his parents. The losses and the long-distance phone call were harbingers of the inevitable. But my biggest problem was immediate (aren’t they all?): Cheryl and Don, as I’ll call them.

Cheryl and Don had grown children, were either world-class social drinkers or textbook alcoholics, possessed a font of knowledge on matters such as how to take advantage of a loophole in the island’s customs law so we could each bring home an extra gallon of rum, and had decided that these two honeymooning 25-year-olds (us) needed their company. No matter where we went or what we were doing—limbo-ing, eating dinner, bronzing ourselves under a punishing sun—we’d hear a little Cheryl-pitched shriek of delight and there they were.

But—as in a mystery novel—it was these two apparently minor and eccentric characters who would offer the most important lesson of the honeymoon.

The four of us were lying on lounge chairs under the carcinogenic Caribbean sky when a young man appeared down the beach from us, offering brochures to tourists. This happened all day long: The brochures were for catamaran rides, or buffet dinners, or happy hours. But when Cheryl caught sight of this particular man, she said, “Oh no! No, no, no,” and began to reposition her chair so that she had her back to him.

“Nope,” Don said, and got to work turning his own chair around. It was a circling of the lounge chairs.

What was going on? “Timeshare,” Cheryl said, the way you might say rape or endoscopy.

Apparently, on a previous vacation, they had been suckered into a timeshare presentation (probably on the inducement of free drinks), and something about it had been absolutely horrible. Cheryl and Don were a couple of seen-it-all New Yorkers; you wouldn’t think a salesperson would get the best of them, but whatever had happened had left a mark.

The lucky Mets hat never turned up. Neither did the jewelry. We ended up tapping out on the marriage at five years—the paper anniversary, which was in our case observed with an 8-by-11 decree of divorce—and going our separate ways. But those five minutes on the beach with Cheryl and Don were forever, and they left me with a dictum to last a lifetime: Never, ever, no matter what, go to a timeshare presentation.

And then Sandra (not her real name) called me.

We’re always on guard for situation-specific dangers—to be careful of riptides when we’re swimming in the ocean, but not when we’re cleaning the lint trap. To keep an eye out for pickpockets when we’re on the tube, but not when we’re getting a mammogram, life’s most pocketless experience. Similarly, we cast a cold eye on the timeshare hustlers who approach us on beaches or ski resorts or on the Las Vegas Strip. Get behind me, Satan. But in our own bathrooms, where we’re putting on lipstick 10 minutes before friends are due for dinner, our soft throat is exposed.

The number on my phone had an unfamiliar area code and lacked multiple zeros, and I was intrigued; had some real person from this unknown (by me) American place misdialed? Or was it a call to adventure? Neither. It was Sandra, telling me that because of my Hilton Honors membership, I’d qualified for a special offer. I could spend five nights at any Hilton Grand Vacations resort for $120 a night.

A question: I’m a Hilton Honors member?

A thought: That’s a really good price.

Here’s what a rube I was. I spent much of the call worrying that I might not be a Hilton Honors member after all and that at any moment Sandra would realize it. How humiliating it would be if she performed the Telemarketers’ Revenge and hung up on me.

I asked if they had a resort in Hawaii, figuring there was no way they could be selling rooms there for $120 a night. Why yes, there absolutely was a Hilton Grand Vacations Resort in Hawaii! It was in Waikoloa Village on the Big Island, and I was going to love it! It was oceanfront! It was 62 acres! There were no hotel taxes (which can run as high as 17 percent in Hawaii) and also no resort charge. (Joe Biden: “Those fees can cost you up to $90 a night at hotels that aren’t even resorts!”)

I tried to think whether I was missing something. Was there anything else I should know? “There’s just one thing!” Sandra said brightly, like it was the best part of the deal. We’d have to go to a 90-minute timeshare presentation.

“Oh no! No, no, no!” I said. “I don’t do timeshares!” A principled stand, although one invalidated two minutes later when I took out my credit card and bought the package.

Afterward, I told myself I shouldn’t feel bad about going against my convictions. The chance that a middle-class American could make it to 60 without going to one of these damn things has got to be small. The reality, I told myself, was that I’d waited 35 years for the right deal.

And besides, what was so important about my precious time that I couldn’t spend 90 minutes of it sitting through a sales presentation?

My Real Husband (let us call him R.H., as those are in fact his initials) picked me up in “as is” condition at a fire sale 30 years ago, and we are a happy union of opposites. He’s in the problem-solving business, and I’m in the problem-having business. Yes, somewhere there are enough lost baseball caps—and one very nice pair of earrings—to fill a few airplane hangars, but he’s not the kind of person who loses his own mind if I lose something. He seems to have some bigger vision for himself—and for us—than worrying about baseball caps.

Still, in the minutes following the purchase, I realized that I really should have talked with him before signing us both up for this potential scam. But I couldn’t have waited! The deal was only good for the length of the call!

I decided to do some research so that when I presented the situation, it would sound like a great decision.

Have you ever Tripadvisored yourself to a goddamn fare-thee-well, to the point that you know more about the Austin JW Marriott (“Excellent rooftop pool”; “pillows should have been replaced months ago”) than you know about the Roman Forum, or, for that matter, your own dwelling?

From that night until we left for Hawaii months later, Tripadvisor reviews of the Hilton at Waikoloa Village were my constant reading material. Typical for the genre, there were odes, comedies, horror stories; the domestic details were nonpareil. The five-star reviews tended toward the Edenic:

“Paradise it is!”

“Heaven on earth.”

Less encouraging—and in some instances revolting—were the many reviews that expressed, in vivid terms, a very different kind of experience.

“Luxury apparently means that the walls are so thin that you can hear your neighbor urinate.”

“The carpet smelled like it hadn’t been deep cleaned for ages! The bathtub had a ring from the previous occupants.”

A pair of honeymooners had complained about their room and been switched, they said, to one in the “basement.” They fired a flare from their dank chamber of delights: “The basement is disgusting! Dark, Musty, Moldy, stained walls and carpet.”

What the hell was going on? Were these two hotels, the former an Elysium, the latter a rendition site of filthy carpets and lies?

Apparently, yes. As I discovered, at the resort, you can stay in one of a few different buildings, including the Makai. The Makai is a Hilton hotel, and people seem to like—even love—staying there. But at the far end of the property is an enormous complex of almost circular buildings that give an impression less of a resort than of a municipal jail designed by an enlightened architect of the 1970s. Here is where you’ll find the Ocean Tower: the locus, it seemed, of many of the bad reviews. That behemoth isn’t a Hilton. It’s a property developed and managed by an entirely different company—Hilton Grand Vacations—that licensed the Hilton name after Hilton itself got out of the timeshare business back in 2017. Sandra had not sold me a grand vacation at a Hilton. She’d sold me a Hilton Grand Vacation.

Goddamn it, Sandra! I’d already proved myself a patsy—and at 61, I worried that I could be a figure in one of those articles called “Top 7 Financial Scams Targeting Seniors.” It was already happening! The cougar years were now over. What comes next? Chico’s and a timeshare?

timeshare office
Illustration by Nicole Licht

I called the reservation desk—my spindly, senior fingers punching in the numbers as fast as they could—and asked where we were booked. Sure enough, the woman on the line told me, we were slated for five nights in God’s smelly waiting room, Ocean Tower. Very calmly, so as not to arouse suspicion that I was already cooling on the timeshare lifestyle, I asked what it would cost to move to Makai. She could have said any number.

By the time we got on the plane, I had spent 12 weeks immersed in Timeshare Horror Porn.

There are, apparently, tons of happy timeshare-presentation-goers who try to build a presentation into every trip. These people whip through the presentations at warp speed, and some huge number of them post about the experience on TikTok, laughing about it and sometimes kind of enjoying it. The vibe is: Don’t overthink it!

But of a very different cinematic character—no views of white beaches or enormous swimming pools—are the reports from timeshare victims. They post not on TikTok but on YouTube: Haunted people explain how they were misled, bullied, detained for hours, and broken down to the point that they’d actually bought something that they couldn’t afford and rarely used and that had death-do-us-part annual fees.

Orlando, Florida, is the undisputed timeshare capital; the Disney Vacation Club is its own shining city on a swamp, but all the big players are there: Wyndham, Marriott Vacation Club, and good old Hilton Grand Vacations. According to the American Resort Development Association (ARDA), more than 10 million American households own at least one timeshare membership, and there are at least 1,500 timeshare resorts nationwide. If you’re not currently sitting in a presentation, you’re ahead of the game.

Timeshares took off in America in the 1970s, when a glut of condo construction near vacation spots blighted skylines and squeezed developers. Getting people to share the ownership of a single condo and each use it a different week of the year was lucrative. From the very beginning, the marketing of these things was sleazy. Since then, regulations have been passed. Almost every state in the union now offers a rescission policy—some period of days during which a buyer can come to her senses and cancel her deal. But the industry still has a lot of tricks up its sleeve.

The Federal Trade Commission’s website devotes a page to “Timeshares, Vacation Clubs, and Related Scams,” warning consumers of the high-pressure tactics employed in their sales offices. It informs visitors to the site that reselling a timeshare you no longer want is extremely difficult. And it says the same thing any accountant or investment adviser would: Never think of a timeshare as an investment that will grow over time. The ROI is the pleasure you and your family take in it, and the probably remote possibility that it will save you money if hotel prices rise precipitously.

We weren’t wheels up over Inglewood before I was immersed in “What have I done?” anxiety. I waved away the breakfast omelet, ordered a fresh-squeezed bourbon, and took a nap, snapping awake an hour later realizing I hadn’t told R.H. about any of these things I’d learned, and that I’d better do it before we got to Hawaii.

I tapped him on the shoulder and told him what we could be up against. When I got to the part about the bullying salespeople who could keep us for hours, he looked at me the way you might look at a weird but beloved item you picked up at a fire sale 30 years ago and can’t quit.

“That’s not going to happen,” he said.

But what did he know? He’s from Minnesota, and he’s always seeing the best in people—an admirable trait that, I must confess, has rarely failed him—but in this situation, it could be our undoing.

We got to the Makai just after dusk, and when we turned into the wide driveway, you could tell immediately that something was off. The hotel was dark. I had read that the hotel was seriously understaffed, even by post-pandemic standards. Only two people were parking cars, in a very ad hoc—though friendly—kind of way. Then we pushed through the enormous doors and into the massive indoor/outdoor lobby. It, too, was minimally illuminated and nearly deserted; leaves scuttled back and forth across the floor.

The only bright place was the reception desk, where we met the greatest employee not just of the Hilton corporation but of any corporation anywhere. He looked like a young Elvis, wore an electric-blue aloha shirt, and was fanatically committed to our happiness. We had a great room; we would be very happy; we could self-park, if we liked, or use the valet; here were our key cards; was there anything—anything at all—he could do to improve our stay?

Everyone on the Hilton’s skeleton crew was extremely kind and helpful. It was as though both workers and guests were stranded together in this weird predicament, all doing our best not to overtax a fragile system. R.H. and I made our own beds, hung up and reused our towels, and instead of bothering one of the rattled bartenders for drinks, used a rinsed-out Frappuccino cup as a cocktail shaker to make martinis at sunset.

The first morning I opened the curtains and saw that we had a vast and unobstructed view of the ocean. It was one of those Kodachrome days you can get in Hawaii, when everything looks like a color-infused travel photograph. The room was furnished in mid-price hotel-room drab, but it was really big. At $210 a night with no hotel tax, I started to feel like the timeshare-presentation lifestyle might be for us. But that was before we went to ours. O Cheryl! O Don! Why had I forsaken you?

The presentation was on the second day, at 2 p.m. Apparently if you’re from Minnesota and have a good attitude and genuinely respect other people, and if you agree to be at a certain place at a certain time, you show up there on time, and in appropriate clothing. Whereas if you grew up in Berkeley and have a bad attitude, you can work up a righteous anger about corporate greed even when you have contracted with a particular corporation for the express purpose of having a good time. So I was halfway through a cheeseburger and fries at the Lagoon Grill, the one place where you could reliably get a decent lunch at the resort, when R.H. tracked me down, eyes widened at my wastrel ways (waffle fries, large Coke, Kindle tilted against a ketchup bottle, all the time in the world) to inform me that we were going to be late.

I quickly signed the check, submitted to having a bit of ketchup wiped off my face, and marched to the parking lot in my swimsuit cover-up and sandals. I really, really didn’t want to go.

We had to drive about a mile to the sales office, which was located in another HGV property, a tidy complex of townhouses. We walked down the type of bright-white corridor usually reserved for passage to the mothership or the final chapter. It was lined with photographs of choose-your-afterlife locations—glowing pictures of happy families, delighted couples, amber sunsets, and endless beaches, all with the HGV logo stamped on a corner.

Three other couples were in the waiting room. All, I sensed, were there under similar conditions. Nobody said a word. R.H. opened his computer; I thought about going to the car to get the rest of my cheeseburger, which would have blown his mind, so I sat still. But then, 15 minutes late and wearing a rumpled aloha shirt, came Moondoggie, as I immediately thought of him—because it was the most beach-tastic name I could think of, and because, like his namesake (Gidget’s boyfriend), he seemed like a person who couldn’t put the screws on anyone.

We went down a gleaming corridor, lined with bright Lucite boxes, which were the sales offices. Each office was named for a particularly exciting HGV destination: Portugal, Waikoloa, Scotland, Seychelles. What taxonomic category united these various entities—two European countries, a census-designated place on the island of Hawaii, and an archipelagic state in the Indian Ocean? It was obvious: They were all places of thrilling and appealing difference that had been shrunk into grab-and-go portions by a benevolent American corporation.

Moondoggie ushered us into Seychelles, I think, but I was so hot with anxiety that I could be remembering wrong. I came out of the gate with a rookie mistake. I felt that we should be very honest that we were not going to buy a timeshare and that we were just there for the cheap hotel room. Moondoggie took the news really well. That was because, as I later learned in my research, I had revealed the pact. Apparently, many couples agree beforehand that there’s no way in hell they’re buying one of these things, and they reveal this fact to the salesperson. At that point, his job is to look for any sign of breaking the pact—an indication that one person is taking an unexpected interest in the arrangement, at which point that salesman swings away from a joint presentation to focus exclusively on the Pact Breaker (presumably until the Pact Keeper either gives in or starts a week-long, vacation-ruining fight).

Moondoggie and R.H. engaged in some “getting to know you” chat, which they were both very good at, while I sat nervously on the edge of my chair until it was my turn to get known. Things petered out exactly the way many of my conversations with strangers peter out, with me saying, “Well, sometimes the editor picks the subject, but a lot of times I come up with one.”

The next two hours were like some kind of social-science experiment, in which we were placed in a small glass box and put under intense pressure to buy something against our best interests. First we were informed that we don’t take enough vacations. The reason we needed HGV was that it would force us to take vacations, a concept that Moondoggie kept repeating during the presentation, each time making the title of Simone Weil’s essay “The Iliad, or the Poem of Force” pop into my head.

Moondoggie then told us in some tricky or possibly just confusing language that what was on the block was the “deeded ownership” of a tiny portion of one particular unit in Waikoloa. But it soon became clear that the place itself was not the point; we might not even be able to spend a day of our forced vacations there. What we’d really be buying were points that could be used to book HGV units around the world on some kind of giant, computerized trading floor.

Each year, we would be given a new infusion of points. But they probably wouldn’t be enough at first to go anywhere good anytime good. The seasons were ranked by precious metals—platinum, gold, silver, and bronze—and the bottom line was Don’t think you’re going skiing anytime soon.

Moondoggie gestured toward a saleswoman sitting alone in an adjoining glass box, who apparently spent a week in Park City, Utah, every winter, and who, he said, seemed to spend all year trying to get seven days in a row in the same unit. One of the many endearing things about Moondoggie was the way he would bond with us by innocently telling us some damning bit of information about the company, for example that it would probably take us several months to learn how to use the booking system, because it’s really complicated.

About an hour in, R.H. took advantage of a lag in the monologue to say, “I want to understand your business model.”

Moondoggie and I both looked at him in confusion, my own intensified by embarrassment—it seemed like a rude question.

“I mean,” R.H. said helpfully, “if I looked at your annual report, what’s the most important source of revenue? Is it the initial sales? Or the maintenance fees? Or the financing?”

Each moment of a marriage is every moment of a marriage, and in that particular one, 30 years of our financial discussions were laid bare. The “price” of a thing always turns out to be a rough sketch of what it’s actually going to cost you.

Moondoggie was stumped by the realization that this good-natured, Minnesotan preacher’s kid understood business in a way that a thousand photographs of Scotland would not change, and at that point we all realized that we were running down the clock. We talked about Moondoggie’s son, whom he was worried about and obviously loved a lot. I asked to see a photograph, and the boy was so handsome and had such an open face that I realized that Sandra in sales had been wrong, and that it wasn’t okay to waste his father’s time making a presentation to us when we knew we wouldn’t buy.

All that was left was the inevitable meeting with the closer: a former football coach of incalculable size with a gray ponytail, a leather necklace with a shark-tooth pendant, and a mess of somewhat disorganized paperwork because, he said, many sales were all closing at the same time all around us.

He told us the deal:

Deed location: Kings’ Land

One bedroom

Deposit today of 10 percent: $3,098

Closing costs: $800

Annual maintenance: $1,368 + $291 (for club-membership dues)

Activation: $199, billed in 45 days

Bonus points: 24,000

Total sale price: $30,980

The unit, in a development near the Hilton, would be our “hedge against inflation.” It would secure us “a lifetime of prepaid vacations.”

Once R.H. politely clarified that we would not be taking that offer, the closer immediately stood up from the desk and made a fast—and, in my opinion, somewhat disgusted—exit. After a few more excruciating sales promotions, Moondoggie finally walked us out to the parking lot, which felt like one of those awkward situations when a man you’ve refused to sleep with walks you to your car, because he’s a decent person, but you both can’t wait to shake each other.

At last we were free and alone, in the intense brightness of the actual sun, on the surface of which we seemed to be walking. At that point, I needed prescription headache medication, over-the-counter Imodium, a cool washcloth for my forehead, and a dark room in which to pray for death.

I glanced over at R.H., for one of those moments of perfect sympathy that occur only in the context of a long marriage, but he wasn’t looking at me—he was looking toward our rental car, lifting the fob with a blissful look. “Nice guys,” he said, and clicked “Unlock.”

Here are a few things to know about buying a timeshare. First, heed my advice and never take out a loan for it. HGV reports that its fixed interest rates can run up to 25 percent a year; in 2022, the company collected a quarter of a billion dollars in financing payments, perhaps with the assistance of its in-house collections division. Annual maintenance fees are another revenue driver. The company does not break out maintenance in its annual report but folds it into a category called Resort and Club Management, on which it collected half a billion dollars last year.

This practice results in a profound hardship for members who hadn’t realized that even in old age they would still be required to pay those fees. Many haven’t set foot on a vacation property in years, and yet HGV still bills them for maintenance. The obvious solution would be to sell the timeshare, but as the FTC pointed out, that’s very, very difficult to do. Look up timeshares on eBay, and you’ll see plenty listed for $1. Some are surely fake, but not all. Why would anyone sell a timeshare for $1? Because they’re desperate to escape these fees.

Fortunately even timeshare owners get to die, but the company isn’t done with you yet. The perpetuity clause in most of these contracts means that the timeshare will become part of your estate—one of your beneficiaries is going to get stuck with those fees for the rest of her life, if she doesn’t file a so-called disclaimer of interest by her state’s deadline.

When The Atlantic reached out to Hilton Grand Vacations, a spokesperson wouldn’t speak on the record about these fees and their effect on the elderly, their children, and other owners who didn’t grasp that they would have to pay this money for the rest of their lives. The spokesperson sent me some boilerplate on the subject, writing: “Hilton Grand Vacations redefined what vacation ownership should be through our flexible model,” and that “this dynamic model is why the vast majority of HGV members are happy with their vacation ownership.” The spokesperson added: “We also understand that life circumstances can change and we are committed to helping our members find the right solution for their needs in the event they need to modify their vacation ownership.”

When pressed multiple times about these matters—for example, about why the company doesn’t make it easier for heirs to cancel a contract—the spokesperson told me that my questions about the “vacation ownership business model” should be directed to ARDA, the trade association. But I wasn’t asking about the industry. I was asking about HGV and the hardships it causes the elderly. At that point, the trail—already cooling—went cold. (As for Hilton itself, when given the chance to comment, it did not reply.)

Everything turned out alright in the end. I have to believe that the compensation Moondoggie gets from the company is enough to justify all the presentations he gives to refuseniks. Besides, his dream isn’t to sell timeshares; it’s to open a breakfast stand. HGV won because these package deals allow them to fill up empty rooms for a little money. And R.H. and I came out even, because we’d had some fun and left the island with all of the possessions we’d brought to it.

This July will be our pearl anniversary, although we always forget which day of the month it falls on, and one of us usually says “Hey, happy anniversary!” a few weeks late. We both were married before, and the dates stuck in our brains are the ones that were sent out on invitations, and that were the occasion of massive blowouts funded by our parents. We never give each other presents; it just seems weird—“Please accept this gift for sticking with me. I really flamed out the first time.”

But it seems like we should probably take a trip or something. I can’t top the time that, on what turned out to be the occasion of our 19th, I took him to a passage grave in Ireland and showed him the big cremation bowl, but I’ll think of something. It will surely be a whirlwind of headaches and upset stomachs for one of us, amortization and struck-up conversations for the other. And that’s what it’s like to be married for a long time. You’re operating on the perpetuity system, and what you want to do is get a couple of umbrella drinks at the edge of a pretty vista every year or so, somewhere you can tell each other your favorite stories, and eventually wander away altogether, sticking your kids with the maintenance fees and slipping off to the place where time is all there is.

The Atlantic