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.<\/p>\n
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\u2019t have the capacity to bounce back from a bad loss.<\/p>\n
With that in mind, here are the top five big purchases that are more likely to be hidden traps leading to regret in retirement.<\/p>\n
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).<\/p>\n
It\u2019s easy to see the appeal: You have a lot of time to vacation in retirement and buying a timeshare seems like a better \u201cinvestment\u201d than buying a vacation home.<\/p>\n
Unfortunately, many of these timeshares are underused and don\u2019t generate a return for their owners. They also have exorbitant maintenance fees that can make the financial picture worse with every passing year.<\/p>\n
These so-called \u201cinvestments\u201d are also difficult to offload. There\u2019s not a lot of secondary buyers available for you to resell and the resale value is often abysmal. \u201cOur 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%,\u201d said Brian Rogers, owner of Timeshare Users Group, a consumer advocacy and timeshare<\/a> resale website, told CNBC in 2024 (2).<\/p>\n Bottom line: steer clear.<\/p>\n Read More: 8 essential money moves to make once you\u2019ve saved $10,000<\/a><\/p>\n Read More: You can now invest in this $1B private real estate fund starting at just $10<\/a><\/p>\n Florida<\/a> 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 \u2014 at least on paper.<\/p>\n However, when you look closer, the picture is a lot more muddy.<\/p>\n Climate change has increased the severity of extreme weather events in this region, which was already prone to hurricanes and floods. That\u2019s pushed up property insurance rates at an accelerated pace in recent years, leaving many seniors stranded with depreciating properties and hefty monthly premiums (3).<\/p>\n Story Continues <\/p>\n \u201cHome ownership in South Florida does not represent the financial stability that it used to,\u201d admits the Miami Herald (4).<\/p>\n 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<\/a>.<\/p>\n 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).<\/p>\n It\u2019s tempting to offer some financial support to your adult children<\/a>, family members or friends in retirement. After all, you have the resources to support their dreams and that new business venture they\u2019ve pitched sounds really savvy.<\/p>\n 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 \u201cserious arguments or conflicts (6).\u201d<\/p>\n A whopping 75.1% said it had a negative impact on their relationship. So, setting boundaries<\/a> and limiting financial support could be the best decision for your retirement plan as well as your close relationships.<\/p>\n 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\u2019s tempting to boost the size of your nest egg in any way possible.<\/p>\n 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).<\/p>\n Adults over the age 60 lost nearly $716 million to cryptocurrency-related scams in 2023 alone.<\/p>\n The next time someone pitches a \u201csure thing\u201d or a \u201ccommunity memecoin,\u201d it may be best to walk away \u2014 no explanation required.<\/p>\n Join 250,000+ readers and get Moneywise\u2019s best stories and exclusive interviews first \u2014 clear insights curated and delivered weekly. Subscribe now.<\/a><\/p>\n We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines<\/a>.<\/p>\n American Resort Development Association (1<\/a>); CNBC (2<\/a>); Nature (3<\/a>); Miami Herald (4<\/a>); Boatsetter (5<\/a>); JG Wentworth (6<\/a>); National Council On Aging (7<\/a>)<\/p>\n This article provides information only and should not be construed as advice. It is provided without warranty of any kind.<\/p>\n","protected":false},"excerpt":{"rendered":"For many people, retirement is synonymous with freedom. 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