H5game8

Home
Retirement
Happy Retirement

I Drive and Collect Classic Cars: Here’s How I Got in the Game Without Spending a Fortune

Are classic cars a hobby or an investment strategy — or both? Either way, the vintage car scene is much cooler than you think.

By Benjamin Tice Smith published 20 December 2025 in Features

When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works.

20th century sports classic cars are lined up at an auto event with California mountains and fog in the background.

As the sun rises over the San Francisco Bay, classic cars line up before a drive organized by Breakfast Club Rally. (Image credit: Benjamin Tice Smith) Share Share by:

Copy link
Facebook
X

Share this article Print Join the conversation Follow us Add us as a preferred source on Google Newsletter Subscribe to our newsletter

It’s early morning, and the sun is just peeking over the horizon as I consider my options for this morning’s drive.

The older cars are both midrepair, so I hop into my 1994 Mazda Miata. It doesn't seem antique to me, but at more than 30 years old, it qualifies as a classic for today’s drive.

After a quick engine check raises no red flags, I close the hood, climb in and hit the gas.

From just $107.88 $24.99 for Kiplinger Personal Finance

Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues

CLICK FOR FREE ISSUE

https://cdn.mos.cms.futurecdn.net/flexiimages/y99mlvgqmn1763972420.png

Sign up for Kiplinger’s Free Newsletters

Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.

Profit and prosper with the best of expert advice - straight to your e-mail.

There's a chill in the air and fog on the San Francisco Bay, but the top is down. At this early hour, the roads are almost empty, so there's nothing to keep me from my destination: A private airport less than an hour north, where car nuts such as me will meet for a cup of coffee and a 100-mile drive before going on with our day.

In an era when the roads are increasingly filled with formless cars with the sex appeal (and to be fair, the reliability) of kitchen appliances, the vintage car hobby has lasting allure.

Driving a classic car, or just going to classic car events, has all the ingredients of a great retirement pursuit: Instant community, rich experiences in beautiful places, and maybe a way to make some money. Driving a vintage car can make running errands around town much more fun, as fellow drivers flash their headlights or give a thumbs-up as you pass.

How to get started as a classic car collector (or even just a spectator)

Classic car prices vary widely. It's possible to snag a classic vehicle for four figures if you're willing to do some repairs or live with cosmetic flaws. A much-sought-after Porsche 911 can fetch six figures, and Ferraris can easily command millions.

However, consider the expense of parts and labor before you buy. Many people will tell you, “The most expensive car is a cheap [insert exotic car brand here].”

Avoid the lure of a fixer-upper unless you know the car well and are an experienced mechanic. There are many cars that have a reputation for robustness (for example, Japanese cars from the 1980s through the 90s have aged into classic status), which can be important for a first-time buyer.

Colorful classic cars lined up at a car show under an "Easy" sign.

(Image credit: Benjamin Tice Smith)

Buying online

Finding rare cars has never been easier, thanks to the internet. Sites such as Bring a Trailer, Cars & Bids and eBay Motors allow you to search for cars worldwide. If you grew up trying to imagine what cars looked like from the abbreviations in classified ads (such as "5SPD/PS/AC/MNRF"), you'll be pleased to find entire portfolios of photos and videos of each car.

Research the market trends and common faults of a particular model, and check the reputation of any seller you are considering. These sites will also help you arrange remote inspections and shipping directly to you (assuming you don’t relish the adventure of driving a classic cross-country, while blindly trusting the previous owner’s maintenance habits).

Front view of a tan, 1948 Town and Country Chrysler convertible car with the head and horns of a Texas Longhorn.

(Image credit: Benjamin Tice Smith)

The car community

The internet made it easy to connect with groups of fellow enthusiasts for a drive or just to meet and check out each other’s cars. Most groups have a vibrant social media presence, and many organize automotive events from the all-encompassing to the exceedingly esoteric.

This morning’s “Breakfast Club Rally,” hosted by one of these groups, casts a wide net, is open to cars old and new and draws a turnout as impressive as the location.

Cars are parked nose-out on a runway with foggy grapevines in the distance. Interesting modifications are highlighted by an open hood or trunk.

I spy a rare Ferrari FF (a 650 HP two-door station wagon of which only 2,291 were made from 2011 to 2016) and a replica of the 1950s Porsche 550 James Dean died in (see below). As rare as both are, there are two of each on this morning’s drive.

A silver Ferrari classic car.

(Image credit: Benjamin Tice Smith)

What to look for in a classic car

You don't have to spend a fortune to participate. My humble Miata cost less than $2,000 and is hardly rare. “Blinking” the flip-up headlights delights young children, and discerning drivers appreciate the upgrades I have made to it.

My Miata has 50 horsepower less than a base Toyota Camry, but it's light, and on the curvy back roads on this rally, it can keep up with the Ferraris with five times the power.

Uniqueness often wins hearts and minds rather than list price or raw horsepower. Often, an excited crowd will form around a particularly wild homemade build or a scorned-in-its-time 70s econobox, while a mint supercar next to it will be ignored.

Three classic cars wind their way along California Bay Area roads with a view of mountains.

(Image credit: Benjamin Tice Smith)

Before you buy: Storage, maintenance and insurance

Cars require a bit more space and upkeep than a coin or record collection. Original paint and chrome need to be protected from the elements, and devoted collectors rent extra space when they outgrow their home garages.

Automobile storage businesses are becoming popular in larger cities; they not only store cars but also keep batteries charged, perform routine maintenance and have them prepped for a weekend drive.

Insurance and registration can also be complex and expensive, but companies such as Hagerty provide collector insurance, and certain states have less expensive registration options for classics that aren’t driven regularly.

In certain states, passing emissions tests can be challenging, especially for modified vehicles, so it pays to be aware of local regulations. A hot-rodded car from Montana might be literally impossible to register in California, for instance.

Mechanically minded retirees can find that time spent making their cars faster, more reliable or just unique is as much fun as actually driving it, especially if they develop a man cave filled with stacks of tools and walls of automotive memorabilia.

But many (most?) drivers never turn a wrench, while professional mechanics provide services ranging from tune-ups to frame-up restorations. Don’t expect a 24-hour turnaround, as many of the best mechanics have long waiting lists.

It can be worth taking the time to find the right person who knows the idiosyncrasies of your particular car. Once-common skills such as fine-tuning carburetors are increasingly rare among younger mechanics, who are taught to diagnose problems with computer scanners rather than their ears, eyes and fingers.

Early 20th century convertible cars with the Califronia coast in the background.

(Image credit: Benjamin Tice Smith)

Classic cars as investments

The car market is a fickle investment strategy. Some misers manage their garages like portfolios, buying low, selling high and putting as few miles as possible on their pampered trailer queens.

But not driving these cars defeats their intended purpose. Making a profit (after the costs of storage, insurance and upkeep) is a rarity unless you're lucky enough to find an undervalued car or put in a great deal of sweat equity in one.

If you find time behind the wheel or under the hood a chore, none of this will make sense. But if you consider the payback of community, accomplishment and adventure the car hobby provides, it might be a great investment in you, regardless of profit.

Car values have cooled recently after a pandemic bubble, as the workforce has returned to the office. If a dream car once seemed unattainable, and YOU aren't returning to the office, it might be worth checking on it. It could be your time to buy a classic.

10 Things You Should Know About Buying a Car Today, Even if You've Bought Before
Moves to Manage the Soaring Cost of Owning a Car
9 Ways Seniors Can Save on Car Insurance
Turn Your Retirement Hobby into Income: The Pros and Cons

Get Kiplinger Today newsletter — freeContact me with news and offers from other Future brandsReceive email from us on behalf of our trusted partners or sponsorsBy submitting your information you agree to the Terms & Conditions and Privacy Policy and are aged 16 or over.

Benjamin Tice Smith

Benjamin Tice Smith has worn many hats in journalism over almost 40 years as a photographer, writer and editor, for Education Week, Business 2.0, Motormouths.com and others. He has been intrigued by old cars even longer, starting with the 1937 Buick he drove in high school.

When he’s not repairing his cars, he can be found exploring remote roads of Northern California in his 1994 Mazda Miata, 1972 Volvo 1800E, or his father’s 1964 Morgan Plus 4.