Mar 16, 2026
For many people, retirement is synonymous with freedom. You finally have the time and resources to enjoy all those items on your bucket list and indulge in your favourite passions.
However, this is also time to be financially cautious. One wrong move can derail your plans and without a steady income from employment or decades of time to invest, you don’t have the capacity to bounce back from a bad loss.
Advertisement
With that in mind, here are the top five big purchases that are more likely to be hidden traps leading to regret in retirement.
1. Timeshares
Timeshares are big business in the U.S. As of 2025, there were at least 1,500 timeshare resorts across the country and the aggregate industry is worth roughly $35.7 billion, according to the American Resort Development Association (ARDA) (1).
It’s easy to see the appeal: You have a lot of time to vacation in retirement and buying a timeshare seems like a better “investment” than buying a vacation home.
Unfortunately, many of these timeshares are underused and don’t generate a return for their owners. They also have exorbitant maintenance fees that can make the financial picture worse with every passing year.
These so-called “investments” are also difficult to offload. There’s not a lot of secondary buyers available for you to resell and the resale value is often abysmal. “Our general rule of thumb is most timeshares sell for between 0% and 10% of their original retail purchase price and the majority of that focus is unfortunately on the 0%,” said Brian Rogers, owner of Timeshare Users Group, a consumer advocacy and timeshare resale website, told CNBC in 2024 (2).
Bottom line: steer clear.
Must Read
- Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake — are you doing the same?
- Thanks to Jeff Bezos, you can now become a landlord for as little as $100 — and no, you don't have to deal with tenants or fix freezers. Here's how
- Robert Kiyosaki says this 1 asset will surge 400% in a year and begs investors not to miss this ‘explosion’
Join 250,000+ readers and get Moneywise’s best stories and exclusive interviews first — clear insights curated and delivered weekly. Subscribe now.
2. Buying a home in Florida
Florida is often considered the dream destination for many retirees. Sandy beaches, excellent weather, low taxes and cheap real estate make it the perfect retirement retreat — at least on paper.
Advertisement
However, when you look closer, the picture is a lot more muddy.
Climate change has increased the severity of extreme weather events in this region, which was already prone to hurricanes and floods. That’s pushed up property insurance rates at an accelerated pace in recent years, leaving many seniors stranded with depreciating properties and hefty monthly premiums (3).
“Home ownership in South Florida does not represent the financial stability that it used to,” admits the Miami Herald (4).
3. Dream cars or boats
It might seem like the perfect time to buy that sports car or sailboat you always dreamed of, but that could be one of the biggest mistakes you make in retirement.
That luxury car is going to be expensive to maintain and fuel, while it can cost thousands of dollars just to park your boat at the marina, according to Boatsetter (5).
Read More: Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it
4. Investments in friends and family
It’s tempting to offer some financial support to your adult children, family members or friends in retirement. After all, you have the resources to support their dreams and that new business venture they’ve pitched sounds really savvy.
But most people who offer such support end up regretting it. According to a 2025 survey by JG Wentworth, 46.6% who either borrowed or lent money to friends and family said it caused “serious arguments or conflicts (6).”
Advertisement
A whopping 75.1% said it had a negative impact on their relationship. So, setting boundaries and limiting financial support could be the best decision for your retirement plan as well as your close relationships.
5. Get rich quick schemes
You may have retired with less money than you expected or slightly lower than your initial target. Even for retirees who hit their target, it’s tempting to boost the size of your nest egg in any way possible.
But that natural temptation is what makes many seniors a prime target for scammers. Many retirees are prone to investment scams that drain their savings, according to the National Council on Aging (7).
Adults over the age 60 lost nearly $716 million to cryptocurrency-related scams in 2023 alone.
The next time someone pitches a “sure thing” or a “community memecoin,” it may be best to walk away — no explanation required.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
American Resort Development Association (1); CNBC (2); Nature (3); Miami Herald (4); Boatsetter (5); JG Wentworth (6); National Council On Aging (7)
You May Also Like
- Turning 50 with $0 saved for retirement? Most people don’t realize they’re actually just entering their prime earning decade. Here are 6 ways to catch up fast
- Inside a $1B real estate fund offering access to thousands of income-producing rental properties — with flexible minimums starting at $10
- Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it
- Here are 5 easy ways to own multiple properties like Bezos and Beyoncé. You can start with $10 (and no, you don’t have to manage a single thing)
Vishesh Raisinghani is a financial journalist covering personal finance, investing and the global economy. He's also the founder of Sharpe Ascension Inc., a content marketing agency focused on investment firms. His work has appeared in Moneywise, Yahoo Finance!, Motley Fool, Seeking Alpha, Mergers & Acquisitions Magazine and Piggybank.
