Gregory had a 2017 Smart ForTwo Cabrio that was recently totaled. It was tiny but it was loaded, and he really loved it. He is looking for another drop-top that is still fun and funky without being too sporty. What car should he buy?

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Here is the scenario:

I am a 59-year-old lawyer living in downtown Charleston, South Carolina. I am married (my wife just graduated law school herself and is studying for the bar) and our kids have fledged. I’ve owned two cars in my life: a 1992 Honda Accord which was the family’s main mode of transportation for 15 of the 25+ years I owned it (i.e. utilitarian) and the 2017 Smart ForTwo Cabrio Prime I replaced it with. It had all the extras (JBL sound system; collision warning; armrest; phone cradle) and I had to special order it from France. That car was recently totaled (not my fault) and appears irreplaceable. I loved that car.

I don’t drive much — under 500 miles a month. I walk to work and typically drive 3-4 times (not days) a week. I sometimes drive to court in outlying counties or the state capital (30, 35, and 110 miles away). Otherwise it’s mainly street driving — beach, movies, concerts, restaurants, visiting friends). I should be getting around $16-20k from the insurance company. I don’t drive enough to justify a big car expense and my wife dries a 2020 Mercedes 300 so my car can be basic transportation. Money isn’t really an issue. I just want a car that brings me joy when I drive it. The nimbleness and open air quality of my SmartCar did.

I definitely want a convertible with heated seats. Small and nimble but not a roadster (I liked the greater visibility the SmartCar offered). Frankly a 2023 Smart ForTwo Cabrio Prime would suit me fine if it existed. I can spend up to $40k, but I would rather not max the budget.

Quick Facts:

Up to $40,000 but would prefer cheaper

Sort of

Charleston, SC

Convertible, heated seats, fun

A roadster

Expert 1: Tom McParland — Ciao!

Gregory, it certainly takes a thinking man to come to the conclusion that a SmartCar is all the transportation they need when most folks are piloting giant trucks and SUVs by themselves. Unfortunately, Smart didn’t quite catch on with the American audience, so direct replacements for your Cabrio are few and far between.

Perhaps it might be time to shift to another interesting but unloved small convertible from Europe, the Fiat 500. Available in both coupe and cabrio for “al fresco” motoring, the 500 is a great city car for zooming around town and enjoying life. It won’t have the rear-drive dynamics like the Smart but you probably won’t notice and the upside is that the Fiat should be a bit easier to service. Surprisingly there seem to be more manuals available than automatics, so if you prefer to row-your-own you have more inventory to choose from.

. This will have all the fun of your SmartCar but at less than half your budget, heck you could even buy two!

Gregory, I’m sorry that you’ve been let down... by the entire auto industry, just about. We are largely deprived of convertibles that are small and fun. There’s your Smart, now axed, and there’s the Fiat, mentioned above. I wish I could say that there’s a new silly Honda droptop or something funky from Ford. Well, Ford is making the rather large and serious Mach E at the moment, and Honda’s S660 isn’t sold in the States.

Another guy encountered a similar conundrum in the late 1980s — . He was a Honda dealer back then and got a corporate trip to the Tokyo Auto Show, where he saw a cute and interesting little convertible, one that was about style not going as fast as possible: the Nissan Figaro. Duncan told Nissan that Americans would gobble up these cars, but Nissan demurred. We never did get them officially sold here, but Duncan swore he’d introduce them when they were legal to import under the 25 Year Rule.

Well, it’s been more than 25 years since that show, and Duncan held true to his word, with tons of practically-new low-mile Figaros for sale at his Virginia and Tennessee shops. I have driven one of these things, and they are a revelation. I .

Expert 3: Adam Ismail — It’s Not Really A Roadster

Gregory, I’m impressed by the lengths you went to procure your Smart and am saddened by its demise. Unfortunately, convertibles that aren’t roadsters aren’t a dime a dozen anymore; it’s one of the many things that makes the modern car market stupid. But you don’t have to go back terribly far to find something quirky that offers open-air bliss, and here’s where I point you toward a car a lot of people don’t like.

The was maligned for not being a sharp enough or punchy enough stand in for a Boxster, Z3 or even a Miata. But that’s the thing — you don’t want a sharp, punchy roadster. You want something fun and different that happens to lack a roof. And the TT is the perfect middle ground. I always loved the simplicity of its design, coupled with Audi’s attention to detail with the interior. Alongside the BMW Z8, this car had the best switchgear in the game. And yes, having satisfying buttons to press is a worthy priority when car shopping — on this hill I will die.

There aren’t a plethora of these out there as you’d imagine, but there that looks immaculate, with 47,000 miles and no reserve. Enthusiasts like to pretend they’re too good for the TT, which is your gain. Unfortunately this car’s in California, but as the price stands at about $10,000 at the time I’m writing this, I’m sure you could find a little room in your budget for shipment. Act fast if you’re interested though — it’s only up for a few hours longer.

Expert 3: Mercedes Streeter — Don’t

My colleagues are all offering you good Smart alternatives. However, as Jalopnik’s resident Smart enthusiast, it is my sworn duty to tell you to never stray from the path of Smart. Once you’re no longer driving a Smart, you will long for when you can own one again. No car will quite fill that hole. A Smart is like a loyal pet: Even after they’re long gone, they can’t truly be replaced. That new and shiny dog looks cute, but he isn’t old Rover.

So let’s get you back into the warm embrace of a Tridion Cell.

Of course, before we do that, it’s also my duty to tell readers that Smart spells its brand and models in all lowercase, so “Smart Car,” “Smart ForTwo” and “Smart Fortwo” are all technically incorrect, but zero capitalization runs afoul writing styles.

Third-generation Smart Cabriolets with gasoline engines are actually pretty rare vehicles here in the States. Few people picked them up before Smart decided to go all-electric before just leaving the country entirely. I found just one (1) in the entire country.

is not the same as your former Prime, but it’s pretty close. You get leather seats and the phone cradle but lose out on the collision radar and the JBL sound. I’ve never found the radar that particularly useful, anyway. But you do get something with this car that you did not get on your Prime: the Sport Package! The Sport Package on this car nets you wider wheels and a slight suspension lower. That makes it better in wind and enhances that go kart feel.

Buy the Smart. Smarts are eternal. Smarts are forever. Stay true to Smart.

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