I am forever debating about which cars are the best cars for the connoisseur like myself, never mind the fact that I have only owned or leased a few in my life. For full disclosure, those were: a 2002 Volkswagen Passat, a 2008 Mini Clubman, and a 2013 Volkswagen Beetle.
However, I have driven and tested plenty of others’ cars—my brother’s (Volkswagen GLI, GTI), my dad’s (Volvos and Saabs), and my friends (BMWs, Mercedes, Audis, Lexuses, Subarus, a Chevy Volt, a Range Rover, etc.). Even a few interesting rentals (Audi A4, Fiat 500L, Kia Optima).
The composition of any car model’s appeal for me is uniqueness, presence, technology, and driving engagement. For instance, my Beetle was underpowered and simply-equipped, but it was fun to drive thanks to a 5-speed standard transmission, and I dug the look of it—squat and bulbous, far superior to the original “new” Beetle. To the uninitiated, it looked like a Porsche (apparently)! Not true, but I was happy to take the compliment.

Wagon life in South Tampa!
My dad’s 2015 Volvo V60 station wagon is less fun to drive, but looks great, functions better than a sedan in terms of storage and space, frankly I think it is a more balanced design than the sedan S60, and it has some neat features that I now consider indispensable. Like: ultrasonic parking sensors, keyless entry/start, and blind spot assist. These features are now widely available on Hondas to Bentleys.
Above all, I strive for uniqueness, and so would never be personally satisfied with a vehicle that I see all over. But, I am also moved by “classics” that define(d) a segment. For buyers like me—connoisseurs—these are statement cars, bucket list cars, and more often than not, ones that require some digging into the online classifieds or by ordering new from the manufacturer in a customized format. That is, other than accepting what is readily available in a standard color combination with a standard set of features.
Standard, pfft!
Uniqueness is not everyone’s priority, sure, I get that for some people a car is a tool and a means to an end. But, a little extra thought and effort are certainly worth it if individuality and originality is important. Here are 9 cars for the connoisseur I would suggest as a definitive classic OR a niche model, not to be overlooked…
(new) Volkswagen Beetle Convertible

2016* Volkswagen Beetle Convertible online configurator
Alright Florida folks, I know drop-tops are all the rage. But no matter how you…cut…it (get it?), automobiles with no roof structure tend to be twitchy and shaky and generally less composed than their coupe counterparts. THUS, I advise to avoid them altogether. And we could all do without the sunburn.
However, if a convertible is a must, why not have one that is: adorable, made for cruising not racing, and isn’t very expensive, so it could be a second or third car instead of your primary….? Enter: the Volkswagen Beetle Convertible.
My personal favorite trim level is bare bones basic, in tonal shades of beige. Perfect for blending in at the beach.
(new) Volkswagen GTI, 4-door or 2-door Hatchback

2017 Volkswagen Golf GTI online configurator
What’s not to love? The GTI is a classic “hot hatch” that breeds muscle tone and agility with practicality. PLUS, base and mid-level trims come with tartan seat upholstery! TARTAN!!!
And, the build quality, tech integration, ambiance, and overall tightness cannot be beat for the price. One of Volkswagen’s best home runs ever, and thank goodness, they’ve never really tried to fix what isn’t broken.
(new or used) Mercedes E-class station wagon

2017 Mercedes E400 4MATIC Wagon online configurator
Minus a Volvo or a Jeep Grand Wagoneer, this is the most quintessential upper crust/WASP-mobile. Made for toting antiques, Saint Bernards, children in polo shirts, and arriving in understated style. Extra points if it’s slightly ragged, its utility well-utilized.
I once heard that E-class wagon buyers are the wealthiest group of Mercedes clients, more than any of the more expensive models. I also was once told the no respectable Benz buyer ever goes above an E-class (like to the behemoth S-class or god forbid, a 3-row SUV).
A 2017 E400 4MATIC will set you back about $75,000 well-equipped. Nothing more is needed. That is all.
(used) R129-generation Mercedes SL500, circa 1990-2002

Mercedes 500SL in Death Becomes Her
Purists will cry foul that the R107 (that was the previous SL, built from the early 70s to 1989) isn’t mentioned, but the R129 (built 1990 to 2002) existed all throughout my childhood and adolescence, and it was oh-so-90s. Joan Cusack drove one in Addams Family Values, as did Meryl Streep in Death Becomes Her, Jim Carrey in both I Love You Philip Morris and Liar Liar. It’s a still-gorgeous design that is dated, but in the best possible way. I wrote about the iconic “SL500” moniker in a blog post a couple of years back.
Later examples of the R129 came equipped with side airbags and xenon headlights, cutting-edge safety for their day. My pick would be one from 1996 or 1997 (loved those particular wheel rims), which can be had for around $13,000, or a pristine 2000 to 2002 model, which can cost as much as $20,000 with low miles.
Here are some for sale:
1996 SL500 (8-cyl), white over tan, 68k miles, located in Savannah, GA, $11,000
1996 SL320 (6-cyl), green over tan, 42k miles, located in Colorado, $15,000
1996 SL500 (8-cyl), black over tan, 41k miles, located in Birmingham, AL, $13,000
(new) Volvo S90 sedan

2017 Volvo S90 online configurator
The “midsize executive sedan” is a crowded, contested, oft-debated segment, and the S90 has only this year jumped into the fray, thanks to Volvo’s Chinese parent Geely and their investment capital. It joins models like the Audi A6, Cadillac CTS, BMW 5-series, Mercedes E-class, Jaguar XF, Lexus GS, and Infiniti Q70. One might even consider the Genesis G80 (Hyundai’s upmarket brand) an option.
Those are all great cars, but the 2017 Volvo S90 takes all of their commoditized features and turns them upside down. The design is fresh, the interior is gorgeous and simple, and very much its own personality. I particularly liked Tom Voelk’s description of the S90’s interior architecture as less IKEA, more Roche-Bobois.
The model skips 6- and 8-cylinder engines altogether, and focuses only on 4-cylinder turbo- and super-charged versions, with front or all wheel drive. Reviews have been generally good, but it, as Volvo tradition dictates, the S90 has plenty of quirks and eccentricities.
It may not be the best-in-class, but it also isn’t everywhere. As nice as the E, 5, or A6 are, they’re boring and ubiquitous, and I like to feel special. Don’t you?
(new or used) BMW 3-series 6-speed standard/manual sedan

2017 BMW 3-series online configurator
The 3-series is even more ubiquitous than the 5-series, and arguably the most basic bitch “expensive car,” as evidenced by all the sorority girls and new realtors that choose it…but it is nevertheless a classic.
Why? Hellooo, it started the small luxury sedan movement!
First it was the 3, then the Audi 90-A4, and shortly thereafter, the Mercedes C, Lexus IS, Infiniti G (now Q50), and myriad other copycats. My dad had a 325i when I was born, which my mom promptly made him trade on a hulking white Volvo wagon with blue vinyl seats.
Current 3s can be had from base stripper 320i guise to decked-out 340i form, from the mid-$30k range to near $60k. This doesn’t include the bananas M3.
I would choose the 330i (recently renamed from the 328i), with lots of options, most importantly of which would be a 6-speed standard shift transmission. I’m sure the auto is lovely, but driving a compact, sporty Bimmer with a dinky P-R-N-D automatic!? It just feels wrong.
Sadly, variations of the 3, like the wagon, GT hatchback, and convertible (4-series) cannot be had with a self-shift at all. So enjoy the sedan while you can.
(new or used) Porsche 718/Cayman coupé

2017 Porsche 718 Cayman configurator
Porsches have become eye-wateringly expensive, not to mention diluted by the likes of SUV and crossover models <insert eye roll>, but the purest elements of the brand can be had for around $60k if one focuses only on the essentials. While the 911 is the most renowned model, it is heavy and expensive and is usually driven by surgeons or attorneys…never a good sign.
Instead, it’s the Cayman, recently rolled in with the Boxter under the “718” designation, that ticks the right boxes: agility, compactness, and simplicity. Only with a 6-speed manual, please. Interesting optional extras include LED headlamps, Burmester hi-fi (only $4,700!), a fire extinguisher, and a painted key to match the color of the car, which includes a leather key fob cover.
Essentials, right?
(new) Ford Explorer

2017 Ford Explorer online configurator
Most SUVs are largely unnecessary; so few of us actually need them to ford rivers or go up steep inclines, or even tow heavy things. THUS, I would argue that the S-U-V that started it all (or most of it anyway), the Ford Explorer, is one of the few worth considering, if you must.
New model Explorers are pretty luxe, pretty slick looking, appropriately brutish and muscular, and don’t cost as much as popular rolling knuckleheads like the BMW X5 or Mercedes GLE, or large eggs like the Lexus RX, Acura MDX. Cue hateful comments…now!
What’s more, many police forces, including Tampa’s, are migrating toward Explorers for their patrol cars. If they’re tough enough for the police…
(new) Honda Civic

2017 Honda Civic Hatchback Sport online configurator
To be equitable across price points, I felt I should include something less German, and the latest Honda Civic is actually one I am excited to tout. Past versions not so much, but the Civic was, wayyyyy back in the distant past, one of the first imports to show American land barges that cars could be economical and ultra-reliable, and cheekily stylish. My mom had one. It was her first car, a yellow one she paid for entirely on her own.
The latest (10th generation, 2016-present)…have you seen it? It looks really excellent. Good face, good ass, and packed full of tech. Only thing I don’t like is that it is a mostly automatic-only car, though a 6-speed is standard on the cheapest trims. The Civic comes in sedan, coupé, or hatchback variants.
Its direct competitors are either bland, including the Volkswagen Jetta, Toyota Corolla, Hyundai Elantra, and Chevy Cruze, or a bit too cheap-feeling for me, like the Mazda 3. Should I find myself shopping in this price range, I would proceed directly to a Honda dealer to test drive one.