I Just Bought My Dream Car Sight-Unseen And I’m Going To Drive It Across The Country Back Home

I’m finally fulfilling a dream I’ve had since I was 15 years old. When I was a teen, I dreamed of driving around Lake Michigan top-down in a Smart Fortwo Cabriolet. Somehow, despite owning five of these cars and having been a big part of the U.S. Smart community for the past 16 years, none of my cars are actually my teenage holy grail.

It’s time I changed that. I just committed to buying a 2009 Smart Fortwo Cabriolet all the way down in Florida after seeing nothing more than a few pictures. Now, I’m going to drive it over 17 hours home this weekend.

I’ve been going through my expansive car roster and losing the cars that really aren’t “doing it” for me anymore. I sold my holy grail camper, the U-Haul CT13. Then I got rid of my trusty six-speed manual Volkswagen Jetta SportWagen TDI. Less than 12 hours after that, I sold my Volkswagen Phaeton. I even sold my rock, the Volkswagen Touareg VR6.

I’m not done selling things yet, but moving forward I’m only keeping my dream cars and vehicles of practical use to me. The Volkswagen Touareg V10 TDI isn’t going anywhere, and neither is my Saturn Sky Red Line – but my second Jetta SportWagen TDI remains on the chopping block.

So, what am I doing buying a Smart Fortwo across the country? Don’t I already have five of those?

As some of you already know, I fell in love with the Smart Fortwo in 2008 when I was 15 years old. It was entirely by accident, too. My dad had either broken or wrecked his Ford Ranger and my mom heard of these new “smart cars” that were supposed to be a cheap way of getting around. In my head were images of cars that drove themselves or something. After all, “smart” in 2008 meant something like the new world of smartphones and other high-tech devices.

Instead, what I got was a tiny plastic car. Smart Center Lake Bluff, Illinois was an experience I hadn’t seen before. The showroom was assembled like an art gallery and the salesman was dressed in a suit. I’m not talking about the cheap kind of suits you’ll see at a dealership, but a suit you might wear to a gala.

I loved every Smart on the floor. Teenage me was obsessed with how Mercedes-Benz fit all the components of a real car into something that could fit in a broom closet. But Mercedes also didn’t stop there. These cars sported plastic panels like the Saturns of my childhood and they were bold in color both inside and outside. I was fascinated with how Smart covered the whole interior in fabric, I loved the full polycarbonate roofs of the Passion Coupes, and I thought the Tridion Cell was brilliant. It was a safety cage but also a prominent design element. That’s so cool!

I went home with a brochure that day and within maybe a week I had it memorized front to back. I went back to school talking about the 999cc Mitsubishi engine and its ravenous output of 70 HP. I talked about how Fifth Gear slammed an earlier model into a concrete barrier at 70 mph. I was teased relentlessly, but I never gave up my dream of owning one. I even had a Smart shrine sort of thing:

I’ve always had two dream Smarts in my head. The first was a Passion Coupe with red panels, a silver safety cell, and a red interior. I then had the fantasy of having the safety cell wrapped in chrome, because why not. My other dream Smart was a Passion Cabriolet with blue panels, a beige interior, and a silver safety cell.

Smart Center Lake Bluff let me drive that very car in 2009. My heart melted.

I’ve been on the hunt for that feeling ever since then. My first-ever Smart was a brand new 2012 Passion Coupe that I still have in my possession today. It wasn’t my red car, but as it turns out, I adore the sky blue even more.

Then I got a fantastic first-generation 2005 Smart Fortwo Passion Coupe for free. Things got weird in 2016 when the 2012 caught fire and I thought it was a goner. My network of friends in the Smart world helped me score a new 2016 Smart Fortwo Edition #1, and I’ve cherished that car ever since. From there, I’ve also picked up my dream Canadian diesel Smart as well as a beater Smart that I use off-road.

Yet, you’ll note that none of those are convertibles. I tried to fulfill my convertible dream in 2018 by buying a 2005 Smart Fortwo Cabriolet sight unseen from a guy in Pennsylvania. Unfortunately, the car was far more of a project than described and it survived literally just two drives before the transmission tore itself apart. I got my dream and lost it in the span of a week. I kept throwing parts at the car, too, but it just wouldn’t drive.

I haven’t stopped searching for my holy grail Smart. Unfortunately, the world of Smarts changed during the pandemic. It used to be that the majority of Smarts for sale all had low miles and a seller was lucky to get more than maybe $6,000 for one. A high-mile Smart was lucky to clear more than $2,500. It’s how I got my 2008 off-road beater Smart for just $1,400 with 100,000 miles.

Then Covid struck, and Smart prices went up – so did the miles. Now people want $5,000 for a car with high miles or even damage, and it’s honestly frustrating. It seems like there was a point when subsequent owners, maybe the third or fourth owners, put tons of miles on these little cars. So now, I’m finding more Smarts with high miles than Smarts with low miles. It’s great to have tons of proof that Smarts are durable cars, but I’m not paying 5 large for a Smart with over 100,000 miles.

So, I’ve been searching for years for a unicorn. I want a second-generation Smart Fortwo with a convertible top, well-optioned, under 70,000 miles, and a price of no more than around $5,500, just like before the pandemic.

Cars like these are few and far between. I’ve found plenty of cars for the price, but most of them weren’t convertibles. The convertibles I did find either had too many miles, too few options, or some glaring issue I didn’t want to fix. Or, their sellers were just unresponsive.

While Smarts are mechanically good cars, their bodies don’t always follow suit. Remember how I said I loved the 2008’s red and blue colors? Well, Smart was bad at making red, blue, and yellow. Cars with panels in these colors often suffer from catastrophic clearcoat and paint failure, making an otherwise good car look like a junker. So, I’ve had to forget about getting one in my teenage dream colors.

The fabric interiors also don’t appear to age well, as you can see above. The tops of the dashboards fade under the sun and the seats seemingly get permanent stains too easily. So, many of the cars with my favorite red or beige interiors now look quite dingy. To make matters worse, the convertible tops are known for shrinking and failing over time, so there’s an increasing number of Smart convertibles out there that have been “converted” into coupes.

My search for perfection has led me to pass up on so many Smarts. Honestly, I’ve lost count. I came really close with a Smart with black panels, 70,000 miles, a silver safety cell, and a red interior with only very little staining for just $3,800. I passed on it because its convertible top had a bent bow. In hindsight, I could have fixed that.

I also came somewhat close last weekend when I looked at a $6,000 convertible with 50,000 miles that appeared to have new red paint and a perfect red interior. All I had to do was remove all of the bits I didn’t want, like the chrome and that “SPORTS” decal:

As it turned out, the “paint” was actually a poorly applied wrap hiding failed red panels underneath. And the interior was rougher than the pictures suggested. Smart panels are extraordinarily rare in the U.S. nowadays, so whoever buys this car will be stuck with wrapped panels and bad paint.

Then I found what I thought was the grail, a fully-optioned Cabriolet with just 46,000 miles over on Florida’s Longboat Key. It had some rust challenges, including having its brake lines replaced due to the salty air, but it was in otherwise better shape than most Smarts up north. Unfortunately, that car will end up as salvage because of Hurricane Helene.

Then I found it, near Gainesville, Florida. The Smart I’ve been searching for.

This 2009 Smart Fortwo offers a combination of condition and mileage I haven’t seen in good long while. The odometer shows just 28,000 miles, the interior condition appears phenomenal, the convertible top works, the paint is great, and the seller is the original owner, who checked every single option box. Yes, this car is technically the wrong color, but everything else is perfect.

It’s even a bit of a weirdo. In late 2008, Smart USA said that 2009 model year cars would not be able to have automatic headlights or automatic wipers at all due to a manufacturing change. But there’s one caveat: 2009s made in late 2008 still had those options. This is one of those weird carryover cars.

The mileage isn’t necessarily correct. This car has been towed behind an RV and the proper way to tow a Smart requires you to disconnect the battery. Doing so disables the odometer. It definitely has more than 28,000 miles. However, I wrote the guide on inspecting used Smarts and everything suggests this is an honest low-mile car. The leather seats are devoid of the severe cracking high-mileage cars get. The roof hasn’t shrunken, the headlights remain clear, the steering wheel isn’t peeling, the driver seatbelt still retracts, and the dash doesn’t look faded. It doesn’t have any of the signs of a high-mileage Smart.

So, based on me observing a few pictures and chatting with the owner, I committed to buying it. I took out the money, bought a plane ticket, and I’m flying down tomorrow afternoon to buy it. Then, I’ll drive it over 17 hours and 1,100 miles back home.

I figure that it should be somewhat hard to lose in this scenario. I’m paying $5,800 for the car, but it has high options, presents well, and should have a lot less rust than any Smart up north. Worst case, I should be able to make back around what I spent. If the car turns out as expected, then I’ll be as happy as a bedbug in a sleazy motel.

To say I’m pumped is an understatement. Of course, I’m a bit scared things won’t turn out well. It’s also a dice roll buying a car long distance like this. If the car isn’t as you expect, you’re sort of stuck between choosing between the car and finding out how to get 1,000 or 2,000 miles back home. If you choose the latter, you sort of have to just write the plane tickets off, too. At the very least, I might be able to use this trip to stop in a place like Tennessee to see if I can help in the Helene effort in some way.

But for now, I’m dreaming that my dream Smart will be waiting for me in sunny Florida. I’ve been waiting years to find a car like this and hopefully, this is what I’m looking for. Then, I get to embark on an awesome road trip.