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A Geezer’s Guide to Buying a Timeshare


One of the advantages of being a Geezer is that I’ve made so many mistakes one more doesn’t seem to matter.

I’m not proud of the UGLY part of my behavior but Charlene and I have bought eight timeshares in the last twenty-four years. This was not good travel planning. As I will show in this blog I should have only bought one.

We bought our first timeshare in Mexico 24 years ago. I know how long ago it was because when we bought our first timeshare we were on our honeymoon in Cozumel.

The GOOD news is that we bought all eight of our timeshares heavily discounted and we get as many as 20 weeks of vacation in Gold Crown Resorts from our eight units. I get this many units by never paying more then the minimum amount of timeshare assets (points or weekly units) for my timeshares. What this means is I try to buy last minute deals and I never get timeshares in their high season. By just using these two rules I can maximize the trading power of my timeshares. For each of the last four years Charlene and I have been able to get timeshares for major trips for our family using this strategy.

In 2013 we took most of our family and some friends to Vegas, over a two week period we used eight time shares and the cost for a 5 star, gold crown resort for that little escapade was around $38 a night. Since 2014 we have done similar family trips to Newport,R.I., Orlando and this year we took about 19 people to Steamboat Springs, Colorado in March. We have also given many trips to friends and our kids and grand kids all at very reduced rates. On top of these family trips Charlene and I will use our timeshares six to eight times a year as we travel. We use the timeshares as a break and try to get three or four weeks at one place. What you will find if you’re traveling extensively is every so often you need a break to just recharge you batteries. Charlene says we don’t vacation we go on relocation.

So the GOOD news is, even though we bought way too many timeshares, Charlene and I are getting some pretty good bang for our buck and we will continue to do so.

Briefly, let me talk about the two strategies’ I mentioned above to reduce your costs of timeshare travel, booking late and never booking high season. In order for you to understand why these two strategies are so powerful we need to talk about the structure of timeshare costs. I break the cost of our timeshare travel tool into four categories. The initial cost of the unit which we will talk about later in the blog. The cost of the timeshare membership with a timeshare company, we use RCI and our cost is about $50 a year. The third cost is the maintenance you pay for your timeshare every year. Charlene and I pay around $3400 a year in these yearly fees for our 8 time shares. Finally, you have the actual exchange fee, which for us averages around $210 for each exchange.

Looking at this set of costs it becomes clear that the more exchanges you can get for each timeshare the less you will pay for each week and the better the deal gets. Let me give you a quick example. Most people who put their timeshare in the RCI bank get one week of travel for a week banked. The math on that exchange might be $500 maintenance fee plus the $210 exchange adding up to $710 cost for the unit for a 7 day stay that’s ~ $101 a day for a unit that would probably cost $200 to $600 a day if you just paid for it as a motel unit. By maximizing our timeshares point value we can stretch the one unit we own into three or even four exchanges and the math looks like this: $500 maintenance fee plus $630 ( 210 X 3) exchange fees adding up to $1130 cost for the unit for a 21 day stay that’s about $54 a day. In this way the flexibility of traveling on short notice and in shoulder seasons has a tremendous advantage. For the sake of simplicity these calculations do not take into effect the initial cost of the timeshare or the RCI yearly dues but I think you get the idea.

I am now going to tell you the strategy Charlene and I should have used to add timeshares to our Geezer Tool Box. This strategy is designed for Geezer’s. As a Geezer you have the flexibility to travel on short notice, during shoulder seasons.

First, don’t buy more then one timeshare.

First, you are going to have to buy a timeshare to get the timeshare tool working for you. When you’re buying a washing machine what’s the first thing you do? Let me answer, “You shop for the best deal.” I heard that scream of anguish, “No, not shopping.” OK Geezers suck it up; you and the spouse are about to go timeshare shopping. Rule number one in shopping for a timeshare is you have to go somewhere with a lot of timeshares.

If I were to go timeshare shopping today I would go to Vegas or Orlando these two destinations have a lot of timeshares that use the “Point” system of exchange.

Your first step is to get invited to timeshare presentations. Do a little research and find out where the timeshare resorts are then just walk into the front desk of the big beautiful resort and say, “Hi I’m crazy and I’m curious about time shares.”

In less then a minute you will be talking to a person who wants to know all kinds of information about you. Do not just jump in and say, “I want a time share.” Play it coy ask questions like how long will it take for the sales pitch? Do I have to buy something, etc? If you play it right the salesperson that your talking to will offer you a great benefit to go to “a free breakfast” and if you’re in Vegas, probably offer you free tickets for you and the spouse to one of the big shows downtown. You have just been hooked by the cost of breakfast and maybe a couple hundred dollars in fantastic show tickets into “90 minutes” of having a high-pressure very smooth, very aggressive salesman try to sell you a timeshare. If your sales man is really making you itch to buy, think about how you will feel if your bite to soon. See my friend in the photo- he bit to soon!

At the appointed time, show up for the little dog and pony show, enjoy the free breakfast buffet and tell your spouse that if you even look like your going to buy any thing to fake a heart attack and get you out of there. In most of these sales pitches you will eat breakfast with a friendly soul that wants to know all about you. During your time with this nice person you will find out what the timeshare scheme is. You will here about trading power, if the exchange system is points or weeks, benefits and basically why their product is the best. Let them know you are interested but it’s just too much money (because it is!!!!!!!!!!).

Watch my lips, this first time to the timeshare rodeo DO NOT BUY, as your Geezer with Passports mentor I will be sad if you end up as foolish as I was.

You and your spouse need to keep looking at each other and keep saying, “ Wow that’s a lot of money!” 

After a while the nice salesman will give up and turn you over to the “First Closer.” This guy will show up with a pen a pad and probably a love for drawing boxes and circles and making you feel like you understand things you are clueless about. You will see the cost of the timeshare he wants you to buy plummet. You will hear crazy stuff like, “this is my best offer,” multiple times. You will feel immense pressure to buy. DO NOT BUY.

Yes, this is me after a rough 90 minute session because it is hard to say no but hang in there!

After haggling like a rug merchant in a fire the guy will finally say something like, “I can’t do any better.” You have now made it by the First Closer, congratulations. In a sad voice ask the Closer if you can have your 2 free tickets to a major Vegas Show and go home. He will be sad but he will take you to the Second Closer.

You thought this was over? The Second Closer is the super slick guy. He or she will ask you how every thing went and then find a way to tell you he or she has one more deal. Hang on to your hat Geezer you are now in the timeshare resale zone. Charlene and I have bought all of our latest mistakes at resale prices. This guy is going to offer you prices that will be twenty of even thirty times less then what you heard up stairs. In a recent presentation Charlene and I sat thru in Cabo San Lucas the deal went from $169,000 to $2500! Keep in mind during this process the type of unit does not matter, your not coming back, all that matters is that you own a timeshare and can put it in the RCI timeshare pool. The drop in price will stun you. Hang in there Geezer, DO NOT BUY. The Second Closer will tell you this is it and the deal is off the table today! How’s that for pressure! Here is where a Geezer should say, ” sorry, I need to think about it.”

One of the last things you will probably be offered by the Second Closer is a split unit. This is a timeshare where you only get your points every other year but you pay the maintenance fee every other year too. We bought our last timeshare as a split unit for $3000 and a maintenance fee of $400 every two years. We bought the unit in Vegas but the actual timeshare was a foreclosure unit situated in the Berkshires a ski resort on the East Coast. This is the type of deal you want! This is the sunset of your timeshare presentation and like all sunsets it’s the best deal.

I would recommend you try to attend two or these of these presentations before you think about buying. If you make it to the person selling the foreclosure inventory you will be looking at the best deals. You probably want a property that deals in Points not Weeks. Most American companies offer points but many foreign companies are still just doing weeks. Points are a more flexible purchase for the Geezer strategy.

Now you and the spouse have been to three or four of these presentations. You have spent maybe 10 hours having these guys tell you why they are the best. You have enjoyed fee shows, dinners, gaming chips and of course buffet breakfast’s every time you went to a presentation. It’s time to buy.

With the Geezer strategy you want the absolutely cheapest timeshare you can find that is an RCI affiliate using the point strategy of exchange. The two year splits are nice because the maintenance fees are split in half. Do not worry about your timeshare’s points value. They are only frosting on the cake.

When you buy your timeshare use your favorite miles card so your stretch your deal to the limit. If the timeshare is three thousand dollars, that’s more miles toward a free flight.

So time to do a recap, you bought your timeshare from the resale market for penny’s on the dollar, You got all kinds of cool gifts for your effort and you got air miles.

Now it’s time to turn that investment into cheap travel to cool resorts. See the second article on timeshares “Geezer’s Guide to Maximize Your Timeshare“.

Disclosure: The opinions expressed in this article are shared our readers with the belief of the author that they are accurate but the author is unable to guarantee the offers expressed herein. supports the businesses mentioned above because they are businesses the author has found to be helpful in saving money while traveling. may get a commission for links on the blog. You don’t have to use our links, but we’re very grateful when you do. Opinions expressed here are the author’s alone, and have not been reviewed, approved or endorsed by our partners

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