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.

With that in mind, here are the top five big purchases that are more likely to be hidden traps leading to regret in retirement.

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.

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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.

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).

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“Home ownership in South Florida does not represent the financial stability that it used to,” admits the Miami Herald (4).

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).

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).”

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.

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.

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American Resort Development Association (1); CNBC (2); Nature (3); Miami Herald (4); Boatsetter (5); JG Wentworth (6); National Council On Aging (7)

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.