Downsizing for a Tropical Retirement

We had too much stuff.

There was no way that all that had accumulated over 32 years of marriage, three kids, and a big home was going to fit into our retirement island home. We had been flirting with downsizing for a few years – now it was time to get serious.

A friend told me that downsizing would be liberating (it is) and that it would be time-consuming (also true). I was eager to begin, though some specifics did give me pause. One big one: What would I do with the wedding dresses that I had carted around for my entire married life? One dress belonged to my mother, who wore it when she married my father almost 70 years ago. The other is my own dress that I wore 33 years ago. My mom’s dress is loosely packed in a cardboard box (horrible storage, I know, especially for a Florida home) and mine is dry cleaned and sealed in a $100 box, which seemed like a fortune at that time. I’ve actually never even opened that box. Wouldn’t it be a hoot if it wasn’t even my dress?

Thankfully, my niece wanted her grandmother’s dress, so I packed it up and shipped it out before she could change her mind. I am happy that the dress is with family and its destiny is now in her hands.

Down to one wedding dress, someone told me to sell it on eBay. Have you looked at the almost 10,000 pre-owned wedding dresses on eBay? A beautiful dress costs less than $100. A “vintage” dress (which is sometimes just a nice way to say outdated and old) is $10-50. Oh, and no one is buying them.

Which brings me to a few of my “aha moments” about downsizing:

Things are only worth what someone is willing to pay you.

People aren’t collecting like they used to and our children are not using china and crystal. My kids don’t want excess stuff to be responsible for. They are spending their money on experiences, not “stuff”, and I happen to think that’s outstanding!

If it means something to you, keep it.

No one is judging you. Well, at least until you die and they have to go through the mess you left… And then, who cares, right?

Be generous.

If a loved one wants an item, give it to them now unless you’re in love with it or are still using it. I’ve found that to be much more fulfilling than items sitting in a forgotten box.


If it means nothing to you, don’t waste your precious storage space on it.

One of my friends takes a picture of her stuff when she says goodbye to it. She eventually deletes the photos too.

Take a realistic look at your closets.

If you haven’t worn it in a year, you should probably get rid of it. Set out what you would pack if you were going on two separate month-long trips. One trip is in the summer and one is in the winter. If it doesn’t make the cut, you probably don’t like it enough to keep it.

Adjust your attitude about donating items.

You are donating it because someone else is able to use it NOT because there is something wrong with it or because you don’t like it. An added bonus is that your local charity is benefitting from your donation. Remember to get a tax receipt. The deduction isn’t much, but it all adds up!

Throw away those things that you are pretty sure no one will ever use.

Goodwill does not want your chipped mug or your Lily Pulitzer sweater with the bleach spot. C’mon! You really don’t even consider it usable/wearable. You will save time for the donation centers who sort and throw away unusable items if you are realistic in your giving.

NEVER pay for storage space!

Your used furniture is worth next-to-nothing. Sell the furniture on Craigslist. Have a garage sale. Use the money for a fantastic trip. Put the rent that you’d pay for a monthly storage space into a fund for next year’s vacation. The only exception to this would be our friends who sold almost everything and are living on their boat. They did keep a storage unit but still win the Outstanding Downsizing Award. Imagine fitting everything you own onto a boat! My husband dreams that we will do this one day. We shall see about that…

–   –   –

I’m a work in progress. I still have too much stuff. Everyone has a different twist on what’s important to them. Life events certainly play a part. I’ve lost loved ones. I’ve settled many estates and disposed of belongings, houses, and farms. One of my brothers lost his life and worldly possessions, including many family heirlooms and keepsakes, in a tragic house fire. Random stuff just doesn’t seem that important now. At the same time, the important – meaningful – things in my life seem priceless.

And if there’s a point to this rant, that’s it. We simply have to decide what is important enough to stay in our lives and what isn’t.

So if you’re contemplating your own moving to an island downsizing strategy and you’re deciding what’s important, remember to live a little. Take the trip. Buy the shoes (you’ve gone through your closet and made room for them, right?). And certainly, eat the cake. Always eat the cake.

My beautiful mom (left) & me (right)


Did you downsize before moving to your island? Was the experience liberating for you too?

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Cindy Farr

About Cindy Farr

Can you really live full time in the Keys? Cindy and her husband Lat are about to find out. After having a second home in the Keys for the past 20 years, they are now moving full time to Islamorada to begin a new stage in life - retirement!

While Lat is a 6th generation Floridian (how many of those do you know?!), Cindy grew up on a farm in South Dakota and has lived in Florida since they were married in 1984. They have always lived where shopping centers, malls, and entertainment were within a short drive. Their communities have been filled with people just like them with growing families and a lot of kid-driven activities. If that wasn't enough, they had their own business and work took every minute of the time they had left.

Now, they've sold their business, their 3 sons are grown, and their beloved dog has died. They are now on their own! It's a little scary but they're looking forward to doing the things they always thought they'd love to do. And they're going to see if they can do them on an island! To follow more of their adventures, check out Cindy's blog,

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20 thoughts on “Downsizing for a Tropical Retirement

  1. This article is very timely for me as my husband is retiring June 30 and we are leaving Marietta, Ohio and heading to a house we bought on St. Croix in 2010 when our first granddaughter was born. Over the last 7 years we have furnished it but it feels different now that we will be living there. So much stuff that was part of our stateside life that needs to be decided (Christmas decorations, family antiques, Waterford crystal, anyone?). Wish me luck!

    • My husband and I moved to St Croix 2 years ago and embarked on a whole house renovation of the house we had purchased 2 years prior. I can relate to the downsizing part of your story. If your house is not air conditioned or don’t use it all the time, you will experience mold growing on everything and that musty smell in drawers, cabinets, books, etc. I looked at my wedding portrait one day and there were droplets of water all over it. The gold leaf frame had actually corroded! I brought many framed photos and the humidity has caused them to stick to the glass and are ruined. Salt and some spices clump up and no amount of rice seems to stop it. All that aside, it is paradise and as I gaze out my window at the gorgeous Caribbean Sea and the picturesque scenery this island has to offer I count my blessings. It was absolutely the right decision to move here and I just can’t imagine living anywhere else. I would be happy to meet with you when you get here and show you around. In the meantime, I can answer any questions you might have.

  2. Hi Cindy,
    I retired 13 years ago and live half the year in the BVI and half the year in a much smaller house ( but it is an awesome geodesic dome one ) in the States. Our house in the BVI is VERY small –only 1000 square feet, AND, since we rent it the other 6 months, I have few precious belongings in it ( and those we lock away in the storage room we did build about 9 years after we lived in the house ). What is interesting to me is that I DO NOT MISS ANY MATERIAL BELONGINGS, EVEN MY GOOD ART COLLECTION which is in the States. I miss my 3 (very adult) sons and my good friends and relatives –but not daily — .

    Our house in the BVI was designed so that the front deck looks like ( and can become ) part of the living room –which makes the house look larger as do the many glass windows and sliding glass doors in each room and the high ceiling in the living room area. Life in the islands is inside-outside. I paint my pictures on an inside or outside dining room size table while looking at the sea , a “studio” even better than my “real” one in the States. So—welcome to retired life in the islands! Since you are going to live there full time, you can bring some of your cherished belongings and I bet quite a few of them, like mine, will be photos of your family. I wake up each morning smiling at my sons and their wives and at the sea and tropical gardens which surround our house.

  3. Ah moving from a 2500 sf house to a 20 foot shipping container was an exercise in letting go and really prioritising. I’d read The Poisonwood Bible first and it was an ever- present reminder of what mattered as we moved to St. Croix.

    Giving things to friends I was moving away from was a way to keep a connection- they had a piece of something they loved that reminded them of my love. That was a no brainer.

    Sadly when I left St. Croix, it was a few boxes and what we could sneak into the car we shipped back. Ten years there really pared me down, and once again I left pieces of me behind and still feel quite whole.

    I loved my island and the family it gave me. I learned so very much!

  4. My daughters were 8 and 10 when we left our 5 bedroom NC home for St. Croix, so they learned downsizing at an early age. I gave them each a box and told them to fill it with whatever toys they wanted to keep, though I secretly stashed a few more I knew would stand the test of time. The airline baggage allowances were much better in those days (1976), so we were able to travel with no extra baggage fees, including a suitcase of frozen beef from my parents’ farm……which nerve-wrackingly was the last bag off the plane.

    Now, as retirees, my husband and I have traveled to 12 countries by housesitting half the year, and find it no problem living out of a carry-on bag – though I do admit it is nice coming home and seeing all the ‘stuff’ I’ve accumulated the last 40 yrs. I think I’m due for another round of downsizing myself, so appreciate your hints and wish you the best in your new home. Hope you enjoy island life as much as we do.

  5. I loved this article, such great advice about giving away “stuff”, I have tons and have started the process. I do not want to sell on ebay and hassle around with more problems. I am just donating it all to various charities and feeling good about that. When it comes time, I am going to see if my local consignment shop will take some of my furniture. I am starting now, with a two year plan, I am not moving to an island, but would like to sell the house and move into an apartment.
    Thanks for a great article.

  6. Loved this article! I too want to retire to a tropical island 🙂
    I’ve started the process of cleaning out closets and cupboards etc…
    I don’t have much of an attraction for material things , so I can part easily with many items . It’s the keepsake things like artwork or projects that my daughter made and gave me that will need to stay with me !
    Thank you for the inspiration! The more articles I read about people picking up and moving to an island makes me realize that I too can do this same exact thing !
    Good luck to you !!

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