Retirement has a way of turning long-held dreams into real possibilities. Maybe yours involves a sailboat on calm water, a motorcycle on an open highway, or a gleaming vintage car in the garage. You have earned that kind of thinking.
But before you sign anything, it helps to know exactly what you are buying. Rob De Lessio, Director of Lead Advisors at Strategic Wealth Designers, shared his perspective on each of the most popular retirement splurges and what they actually mean for your wallet.
Boats: A Lifestyle Investment, Not a Financial One
There is a reason people joke that a boat is just a hole in the water you throw money into. De Lessio says that himself. Boats lose value over time and come with a steady stream of costs: fuel, maintenance, storage, docking fees, and insurance.
None of that means you should skip it. It means you should go in with your eyes open. As De Lessio puts it, if it is something you have dreamed about for years and you can comfortably afford it, he says go for it. Just frame it as a lifestyle investment, not a financial one.
Motorcycles: More Affordable, But Know the Tradeoffs
A motorcycle costs less upfront than a boat and delivers its own sense of freedom. Like boats, though, motorcycles are depreciating assets. Insurance, maintenance, and storage add up over time.
There is also a safety consideration worth taking seriously. According to the National Highway Traffic Safety Administration, riders 50 and older made up just 3 percent of all motorcyclist deaths in 1975. By more recent data, that figure had climbed to 33 percent. Proper training, good protective gear, and choosing a bike that fits your physical capabilities all make a real difference.
Vintage Cars: The Best Shot at Holding Value
Of the three classic retirement toys, a vintage car gives you the best chance of appreciation. But De Lessio is careful here. Certain rare antique cars or collectibles may grow in value over time, he says, but that is the exception, not the rule.
Restoration and ongoing upkeep can require significant time and money. Do not count on a classic car to pay for itself unless you know the market well.
The One Option That Could Actually Pay You Back
If you want both enjoyment and a potential financial return, De Lessio points to a vacation rental property. A well-located rental can appreciate over time, generate income, and give your family a place to gather for years to come.
Unlike boats, motorcycles, and cars, real estate can also offer estate-planning benefits. That said, it brings its own responsibilities, like maintenance, taxes, and insurance.
The Bottom Line
De Lessio’s advice cuts through the numbers pretty cleanly. If you are buying one of these things, buy it because it brings you joy, creates memories, and fulfills a lifelong goal, not because you expect it to improve your balance sheet.
The best retirement purchase is not always the one with the highest return. Sometimes it is simply the one that helps you finally live the life you spent all those years saving for.
