A Look at a Four Week Timeshare Vacation 

Yes I own a timeshare and it has been wonderful. My family has been enjoying our timeshare for 30 years and have found it to be far less expensive and a lot nicer than any other available vacation accommodation option. My wife and I recently finished a great timeshare vacation encompassing four back to back timeshare trades around the western and southern shores of Lake Michigan.

For those of you who have mistakenly thought that timeshares are an expensive option, or didn’t know you could trade a timeshare for over 4,000 vacation locations all over the world, I have written, A Guide to Loving Your Timeshare: How to get the most for your money in family fun and experiences, which will be released on August 30th. This book will dispel all the myths about timeshares that seem to persist in the blogosphere and teach you who should own one and how to use it well.

Since we have never explored this part of the country, we were looking forward to discovering what fun things are in each of these timeshare locations. We already know that timeshares are built in places that have a great draw for people. We wanted to find out what drew everyone to the Lake Michigan area. Since we are planning to walk across Spain next summer, we recently began training for that adventure so planned to do a lot of hiking on this trip.

To get to the Lake Michigan area we decided to try a mode of transportation that we hadn’t done before. So we headed across the country from Portland, Oregon to Chicago, Illinois on Amtrak’s Empire Builder train route in a sleeper car. This 46 hour trek took us through the beautiful Columbia River Gorge and Northern Montana. I will detail our experience riding the train in an upcoming post.

We arrived in Chicago and spent the first few days in a hotel exploring the big city in the area of town called The Loop. During this time we attended three musicals and a free concert in the park with a full orchestra and a 100 person choir. We walked on the beautiful paths along Lake Michigan, which run for miles, and even watched a fireworks show they have every Wednesday evening in the summer. 

We also visited the planetarium, went on an architectural boat tour of the city, and rode the hop-on-hop-off bus tour of the city. We tested some of Chicago’s culinary favorites like deep dish pizza and the Chicago dog. There was lots more to do but we ran out of time. Everything we did was within walking distance of our hotel.

The cost of the five nights in the hotel, which was a bedroom and a bathroom, came to $1585. That is similar to our total cost of staying in the timeshares for almost three weeks, including the purchase price and all associated expenses of the markedly better accommodations the timeshares offered. Four days in a hotel is about the same cost as three weeks in a timeshare. I detail all the costs in my book. Following are the places we stayed and what we found. 

South Bend, Indiana

When we left Chicago we rented a car two blocks from the train station so we could easily return it for the train trip home in four weeks. We drove two hours to our first timeshare trade in South Bend, Indiana, having no idea what we would find at this location. We were not disappointed. 

After arriving we learned we were near the home of the University of Notre Dame. It surprised me that I hadn’t realized this before. We took a phone app walking tour of this incredibly beautiful campus and the outstanding church whose inside rivaled the cathedrals of Europe. We found the home of the old Studebaker automobile factory and toured their great auto museum. 

Another great discovery was the nearby town of Shipshewana, Indiana, which is in Amish country. There we saw a new musical and two concerts at the Blue Gate Music Hall. 

We toured a great historical museum of the Amish/Mennonite people called Menno-Hof. This was a fantastic stop. We also took a horse and buggy ride with Buggy Lane Tours and had an immersion into the Amish culture. This was a half hour ride to visit an Amish dairy farm where I milked my first cow. Did you know that fresh milk tastes just like the milk we buy in the store? That evening as part of the tour we went to an Amish thresher dinner. This was at a private Amish home where a meal was recreated just like when all the neighbors get together to thresh wheat. While we ate, we visited with the tour guide who had grown up Amish and later converted to Mennonite. I ate way too much and discovered Amish peanut butter which is my new favorite. We tried out several restaurants in the area and we savored many Amish dishes. We came away with a good understanding of the Amish people and what they believe.

We took a day trip 90 minutes north to the town of Holland, Michigan. This is one of the places the Dutch settled when they immigrated to the United States in the 1800s. There is an authentic Dutch windmill there imported from The Netherlands. Nelis’ Dutch Village was a fun stop that little kids would love and if you don’t know about Stroup waffles, which you can make here, you don’t know what you are missing. We then wandered through old town and thought about taking the boat ride onto Lake Michigan but postponed this for later in the trip. 

Mishicot, Wisconsin (East of Green Bay)

On Friday morning we packed up to head off for the next town on our adventure, Mishicot, Wisconsin, a short five hour drive away and about 30 minutes outside of Green Bay, Wisconsin. We listened to audio books I checked out from our local library during these car rides to change locations which helped pass the time.

This timeshare was located on a 54-hole golf course and is where we first learned about the Ice Age Trail; a 1,000+ mile hiking trail winding through Wisconsin. We hiked it at several locations throughout our stay in Wisconsin and discovered that the local mosquitos know about this trail too. We also hiked along the rivers and the lakeshore. 

Our best discovery was Door County. This is a peninsula with Green bay to the west and Lake Michigan to the east. What beautiful country this was to drive through. I would love to go biking here. We had a picnic on the beach trying out the local specialty, smoked white fish.

This week we saw two musicals with many more to choose from. We visited the Green Bay Packers football stadium, Heritage Hill State Park, and Death’s Door Maritime Museum.

A local crop here is cherries and we had them prepared many different ways while eating out. I didn’t know there were so many different cherry dishes. 

Oconomowoc, Wisconsin (West of Milwaukee) 

Our next stop was in the Milwaukee area made famous by their many beer brewing companies and the TV shows Happy Days and Lavern & Shirley. 

Here we booked a boat tour of the Milwaukee area which started in the river flowing through the city with lots of draw bridges to let us through and even continued out onto Lake Michigan. We hiked along the Ice Age Trail again as well as the river walk. While walking on the river walk we stumbled onto a bronze statue of “The Fonz.”  I couldn’t resist getting my picture with him.

Milwaukee is the birth place of Harley Davidson Motorcycles. Touring their museum was very fascinating. The evolution of motorcycle designs over the last 100+ years of production was fun to see. Nearby was a coffee roasting factory where we learned about how coffee beans are grown, picked, cracked, and roasted. Upon leaving the tour we were given free samples and souvenirs. 

We went to a beach to put our feet into Lake Michigan, watched locals playing on what they call the third beach (or ocean) in North America and the boats sailing out of town. 

Norway, Illinois (West of Chicago)

Our final stop was in the little town of Norway. This is where the Norwegians settled in the 1800s. There was a little museum teaching about their settlement in the area, but it turns out to only be open on weekends. I found it on Monday, so we missed it. 

The bad news this week was I injured my foot. Our hikes had increased to seven mile treks when foot pain brought it to a halt. We were planning on doing lots of hiking in this area but now I needed to rest my foot for a few weeks. So going with the flow we adjusted our plans. This timeshare had two great swimming pools, one indoor and the other outdoor. We changed up our exercising to zero gravity water workouts to let my foot rest. 

Since I was trying to reduce my walking, we ended up watching a lot of movies at this stop. Each timeshare had free DVDs to check out and watch. Having watched a few movies so far throughout our trip, our movie watching increased now that I needed to be off my feet. Without the hiking, we watched movies almost every night sometimes an additional one during the daytime. 

Two evenings we attended musicals. We explored the I&M Canal that was dug to connected Chicago to the Mississippi river. That canal is what made Chicago flourish in the 1800s. We rode on the canal in a mule drawn boat. To save my feet yet still have adventures, we took a 7-mile canoe trip on the Fox River. My back was not happy for the next few days after paddling for 2.5 hours, which we had not done in a long time. 

This timeshare was adjacent to a water park and located on a golf course. They also had a miniature golf course, tennis/pickle ball court, a restaurant as well as other activities. 

Ride Home

As our four-week timeshare adventure came to an end, we dropped our car off at the car rental lot near the train station in Chicago and headed for home, via the Colorado Rockies on Amtrak’s California Zephyr route. This is said to be the most beautiful train ride in the country. 

All in all, we had a fun time. If we had made this trip when our kids were little, we would have included things that the kids enjoy and would have not attended so many musicals. We would have hit all the water parks and kid friendly adventures along the way. The timeshares also have many daily kid activities. Without planning our activities before we left on our trip, we were not disappointed by what we found in the area. After arriving at each location we looked through the brochures and found the things we wanted to do and were able to make the reservations after our arrival. 

What about the costs? Everyone wants you to believe that timeshares are very expensive, but they are very inexpensive in reality. The cost of the four weeks we spent in the timeshares totaled: $2,520. That includes all costs of buying, maintenance fees and trading fees. The cost of the five days we spent in the hotel: $1,585. Times shares provide a much better place to stay at a substantial discount. 

Timeshares are a great way to vacation. I love getting up when I want and walking into the kitchen to make my breakfast. Not having to get dressed before going out to eat breakfast is one of my favorite features of our timeshare vacations. You can also get this with an Airbnb, but at a much higher cost and without all the great amenities the timeshares have.

Check out A Guide to Loving Your Timeshare: How to get the most for your money in family fun and experiences to learn how to best use your timeshare for maximum fun. Release date is August 30th. Timeshares are considerably less expensive than staying in a hotel or Airbnb and have a whole lot more great features than any other available accommodation option. I spell out who is the best person to buy a timeshare in the book. When the right people buy in the right way and know how to get the most of their purchase, timeshares become the best and most economical vacation option you will find.

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6 thoughts on “A Look at a Four Week Timeshare Vacation ”

  1. Hi Cory, so glad you enjoy your timeshare vacay. I have a one week timeshare near the Orlando attractions. It’s a two bedroom in July. I would like to sell it as our kids are grown. What is your advice? Dee

    • Dee, my advice would be to learn how to get great value out of your timeshare and use it, don’t sell it. You already own a gold mine of vacations. You can get even more out of it now that your kids are grown.
      Let’s say you start trading it for multiple weeks a year, like 6. That means you could go on two vacations, and your kids could use 4 vacations each year all over the world. If you have several people to spread it out, you can really get a lot of use from the timeshare since your collective vacation time gets bigger.

      My kids are now grown, so they can use weeks as well as us. Sometimes we all go together. In 2022, so far, my wife and I have been on five weeks of timeshare vacations, four around lake Michigan, and one in Oregon. The one in Oregon was supposed to be for the entire family and a scheduling problem came up and it became only my wife and I. One son took some friends with him to a timeshare in Orlando to do Disney and Universal Studios. The other son used a week to take his family to a mountain retreat in Yosemite, California. I used another week to trade into a week in Orlando four miles from a conference I was attending.

      If you consider the fact we already own the timeshare (just like you do) as a sunk cost and only look at the costs we had for this year (and each year going forward) you would find the following:

      Maintenance fees: $733
      RCI Membership: $80
      Trade Fees for eight weeks: $1494
      Two Guest Certificates: $188
      Total expenses $2,495
      Cost per week of vacation: $2,495 / 8 = $311 per week.

      Where else can my family (or yours) find great vacation housing for $311 a week?

      Don’t sell it, learn to use it!

      Do that for your family. Keep the timeshare, learn how to use it and go have fun for a bargain.

      If you really don’t want to have all this inexpensive family fun, you can get rid of your timeshare and pay higher prices for your future vacation housing. There are several options spelled out in my book in chapter 6, Selling Your Timeshare. For $0.99 you can get the Kindle copy and learn all about it.

  2. I would like to share a negative aspect of timeshares. My parents paid $7000 for “ownership” of a timeshare 15 years ago. My Mom died last year and my 85 year old father has mobility and other health issues and can’t travel anymore. The timeshare has refused to let my Dad out of his 30 year ownership even after my Mom died and he has to pay annual fees even though he doesn’t travel anymore. My siblings and I have no interest in any of the timeshare locations. We can find much better deals on AirBnB than the daily additional timeshare use fees, and we all own additional vacation rental properties we share with each other. But my Dad will have to pay these annual timeshare fees until he dies.

    • Heather/RocDoc,
      I’m sure there will be plenty of people who feel the need to share the “negative” aspects of timeshares, even though they don’t actually own one. That has been the problem. No one speaks up for the positive aspects of timeshares and the people who have learned how to get the most out of their timeshares are not teaching others to do the same. It is hard to imagine that none of the 4000+ timeshare locations you could trade you father’s timeshare for are good enough. When you learn how to get the most out of the timeshare experience, you will find them to be a very economical choice. I own one week a year (only one maintenance fee) and so far this year my family has used seven weeks of timeshare vacations trading that single week. Since your father is not using the timeshare, that is already owned, why not learn to take advantage of the opportunity? You might be surprised about the good trades you can make and the low cost of vacationing at a five star timeshare resort. I just looked and there are currently 2,830 different resorts with availability to trade into right now and 931 of them are gold crown/five star resorts. Florida, Southern California, Arizona, Las Vegas, Hawaii, The Caribbean, Mexico, France, Spain, Australia, South Africa, Brazil……. I’m sure you could find someplace you or one of your siblings or even a friend would like to go. Since it’s there, learn how to use it. I’m sure your father would love to see his kids using it.

        • Tom, I used an entire chapter in the book teaching how to do this. But one short answer is getting value for a trade. If my week is worth 35 points and I trade it for a week worth 3 points, I still have 32 points left to trade. Then if I trade it for a 7 point week, I still have 25 points to trade. The lowest I have seen is 3 points for a trade. If I really looked for value and traded only for three point deals, I could trade for 11 weeks with a 35 point week of ownership. Then I would have used up my trading points. After that there are still ways to get even more weeks of vacation. If you really are wanting to learn how to get super value for your ownership, you need to read the book as I can’t spell it all out in a blog.


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