There’s something magical about pointing a classic car south and letting the miles melt away. Maybe it’s the way chrome bumpers catch the afternoon sun, or how a properly tuned V8 sounds bouncing off old brick buildings in sleepy Southern towns. Whatever it is, these rolling pieces of history turn a simple drive into something your grandkids will hear about for years. It’s a level of nostalgia that kids today can hardly comprehend.

The South practically begs for classic car travel. Those long, sweeping highways were built during the golden age of American automobiles, and they still feel perfect for cars with actual style. You know, back when designers used curves instead of focus groups and when “horsepower” wasn’t just a number on a spec sheet. It was to feel alive. 

Chevrolet Bel Air Convertible

The Stats: 265 cubic inch V8 and enough chrome to blind a satellite.

The Bel Air is the classic. This is the car your dad points to at car shows while telling anyone who’ll listen about the one he should’ve never sold. With its distinctive side spear and numerous two-tone paint combinations, the 1955-’57 Bel Air practically invented the American dream on wheels.

Here’s the insider knowledge: the ’55 was Chevy’s first year with a V8, the ’56 got the styling updates, and the ’57 became the legend. All three years will cruise happily at 70 mph all day long, though your wallet might file a complaint about the fuel economy. But who’s counting gallons when you’re rolling through Georgia backroads in America’s sweetheart?

The convertible’s soft top mechanism is surprisingly robust, but always carry a manual crank; just in case technology from the Eisenhower administration decides to take a coffee break.

First-Generation Mercury Marquis

The Stats: 390 or 428 cubic inch V8 and a ride smoother than your apology after forgetting an anniversary.

The Marquis is what happens when Mercury decides to build a car for adults who actually have places to go. While your buddy’s muscle car is shaking his fillings loose, you’re gliding down Interstate 75 in air-conditioned comfort, wondering why anyone thought bucket seats were a good idea for road trips.

This is luxury without the pretense; no need to explain to the valet why your car sounds like a barely contained explosion. The 428 Super Marauder engine will move this big sedan with surprising authority, though “fuel efficient” wasn’t really in Mercury’s vocabulary back then. Think of it as paying tribute to an era when oil was cheap and cars were substantial.

The best part? Nobody restores these, so you can actually afford one that runs. Your neighbors will ask what it is, giving you the perfect opportunity to educate them about Mercury’s brief moment of brilliance.

Ford Thunderbird Convertible (First Generation)

The Stats: 292 or 312 cubic inch V8 and the kind of style that makes grown men reconsider their life choices.

The first-generation T-Bird was never intended to be a Corvette killer; it was meant to be better than that. While Chevy was building a sports car, Ford created the “personal luxury car,” a concept so successful that everyone copied it for the next forty years.

These early Birds are still the perfect size for American roads. Big enough to be comfortable, small enough to actually fit in parking spots from the 1950s. The removable hardtop is genius – enjoy sunny day cruising with the security of a solid roof. Plus, unlike later Thunderbirds, you won’t need a CDL to park this one.

Fair warning: The trunk is about as useful as a screen door on a submarine, so pack light. But when you’re cruising through Asheville with the top down and Elvis on the radio, luggage space suddenly doesn’t seem that important.

Read more: The History and Evolution of the Ford Thunderbird

Fourth-Generation Chrysler New Yorker

The Stats: 383 or 440 cubic inch V8 and enough room inside to hold a small wedding reception.

I know it’s called the “New Yorker,” but this beauty belongs on the Southern country roads. The New Yorker is what Chrysler built when they wanted to prove they could out-luxury Cadillac without all the chrome excess. This is understated elegance; the automotive version of wearing a perfectly tailored suit instead of a tuxedo with sequins.

The 440 big block is one of Mopar’s finest engines, with torque that’ll move this substantial sedan with surprising ease. The torsion bar suspension, a Chrysler specialty, gives it a ride quality that modern cars would envy. Plus, the build quality was rock-solid – these things were overengineered in the best possible way.

Here’s what makes it perfect for Southern touring: enormous trunk space, air conditioning that actually works, and a presence that says, ‘ You know quality when you see it. ‘ Park this next to a modern luxury sedan, and suddenly that German engineering doesn’t seem so impressive.

Cadillac Eldorado Biarritz

The Stats: 365 or 390 cubic inch V8 and enough tailfins to communicate with aircraft.

The Eldorado Biarritz is a parade float that is also street legal. This is what Cadillac built when subtlety wasn’t even in the corporate dictionary. More chrome than a 1950s diner, more fins than a shark convention, and more presence than a presidential motorcade.

The Biarritz was Cadillac’s flagship convertible, which means it got every luxury option they could think of. Power everything, air conditioning that could chill beer, and a ride so smooth you could perform surgery in the back seat. The 390 engine provides effortless power, though “effortless” is relative when you’re moving nearly three tons of American excess.

Road trip reality check: You’ll spend more on gas than most people spend on car payments, but you’ll arrive everywhere looking like you own the place. Sometimes that’s worth the extra stops at Texaco.

Second-Generation Pontiac Grand Prix

The Stats: 400, 455, or 428 cubic inch V8 and a hood long enough to land small aircraft.

The Grand Prix represents Pontiac at its absolute peak: when it understood that luxury and performance didn’t have to be mutually exclusive. The distinctive long-hood, short-deck proportions became the template for personal luxury coupes, and 40 years later, it still looks right.

The base 400 engine is plenty for cruising, but the 455 turns this elegant cruiser into a legitimate sleeper. The ride is composed without being boring, the interior is genuinely luxurious, and the styling has aged better than most of our high school yearbook photos.

What makes it perfect for Southern touring? It’s sophisticated enough for Charleston, powerful enough for mountain passes, and distinctive enough to start conversations at every stop. Plus, parts are still available, so you won’t be stranded in some small town playing “name that gasket.”

Pontiac Bonneville Convertible

The Stats: 389, 400, or 455 cubic inch V8 and a back seat that’s actually usable.

The Bonneville was Pontiac’s full-size luxury convertible, which means it was built for exactly this kind of trip. Generous interior space, a solid convertible top mechanism, and enough trunk room for everyone’s luggage – assuming everyone packs like normal humans instead of preparing for a moon landing. Don’t worry, folks, the South has grocery and retail stores if we don’t want to pack the entire house.

The wide-track suspension, a signature feature of Pontiac, provides stability that most convertibles can’t match. No cowl shake, no structural flex, just solid confidence on winding mountain roads. The 455 engine provides effortless highway cruising with enough reserve power for passing that slow-moving RV blocking the scenic view.

The convertible top hydraulics are generally reliable, but always check the fluid level before a long trip. Nothing ruins a road trip like wrestling with a manual top in a sudden thunderstorm.

Buick Riviera (First Generation)

The Stats: 401 or 425 cubic inch V8 and styling that still looks modern six decades later.

The Riviera is proof that Buick once knew how to build cars that made people stop and stare. Clean lines, perfect proportions, and not a single piece of unnecessary chrome; this is automotive design at its finest. While other manufacturers were adding fins and fake vents, Buick created something timeless.

The 425 Nailhead engine is smooth, powerful, and surprisingly reliable. The suspension tuning is more sophisticated than that of most cars of the era, providing a ride quality that’s composed yet not isolated. This is a car that encourages spirited driving while maintaining grand touring comfort.

Here’s why it’s perfect for Southern roads: It’s distinctive without being flashy, comfortable without being boring, and reliable without being common. You’ll pull into every destination knowing you arrived in something special.

Oldsmobile 98 Convertible

The Stats: 425 or 455 cubic inch V8 and enough presence to make lesser cars move aside.

The Ninety-Eight was Oldsmobile’s flagship, their answer to Cadillac without the Cadillac attitude. This is understated luxury: the car your successful uncle drove when he wanted comfort without the showoff factor. Generous proportions, quality materials, and attention to detail that modern manufacturers could learn from.

The Rocket 455 engine is one of the great American V8s: smooth, powerful, and remarkably efficient for its size. The Turbo Hydra-matic transmission is bulletproof, and the air conditioning will freeze your coffee in July. For long-distance touring, few cars from any era do it better.

The convertible top is well-engineered and reliable, though like all GM convertibles from this era, it’s better to put it up before washing the car. Trust us on this one.

Third-Generation Ford Galaxie

The Stats: 302, 390, 427, or 428 cubic inch V8 and proportions that make modern cars look awkward.

The Galaxie represents Ford’s full-size cars at their absolute best. Clean styling, quality construction, and engine options ranging from economical (relatively speaking) to absolutely insane. The 428 Cobra Jet turns this family sedan into a legitimate muscle car, while the 390 provides the perfect balance of power and practicality.

The suspension is tuned for American roads, offering a smooth ride on highways, composed handling in curves, and sufficient comfort for all-day driving. The interior is spacious and well-appointed, with materials that have aged gracefully. This is what a full-size American car should be.

Road trip bonus: Parts are available, mechanics know how to work on them, and they’re still common enough that you won’t have people climbing on your car at every gas stop. Sometimes flying under the radar has its advantages.

Lincoln Continental Convertible (1960s)

The Stats: 430 cubic inch V8 and enough gravitas to negotiate international treaties.

The ’60s Continental is American luxury at its most refined. Clean, elegant styling that avoided the excess of its contemporaries, quality construction that justified the premium price, and presence that made other cars seem somehow inadequate. This is the car presidents rode in, which tells you something about its character.

The 430 engine delivers effortless power, while the automatic transmission is as smooth as silk. The air conditioning is powerful enough to create a comfortable environment, and the ride quality is so smooth that you’ll arrive more relaxed than when you left.

Fair warning: The suicide doors are cool, but they’re also suicide doors. Ensure that everyone understands how they work before passengers attempt to figure it out on their own. Additionally, parts are expensive, but quality has never been cheap.

Second-Generation Chevrolet Impala

The Stats: 235 inline-six or 283, 348, or 409 cubic inch V8, and fins that make the space program jealous.

The ’59-’60 Impala represents the absolute peak of American automotive excess. Those fins were a statement of intent. This is what happens when designers are told to make cars look like rocket ships and nobody mentions fuel economy.

The SS 409 is the stuff of legends: enough power to embarrass much smaller cars, with a sound that’ll set off car alarms three blocks away. However, even the base V8 provides ample power for touring, with a ride quality that makes modern cars feel harsh by comparison.

Here’s the thing about driving a finned Impala through the South: you’re piloting a piece of American optimism. Every small town will remember when these were new, and half the people you meet will have a story about one just like it.

Plymouth Fury Convertible

The Stats: 273, 318, 383, or 440 cubic inch V8 and styling that proves Plymouth had a sense of humor.

The Fury is what happened when Chrysler’s practical division decided to have some fun. Those tail fins are cheeky rather than excessive, the styling is distinctive without being weird, and the whole package has a sense of joy that’s infectious. This is a car that wants to be driven, not just admired.

The 440 engine is one of Mopar’s finest: massive torque, surprising refinement, and enough power to make highway merging a non-issue. The torsion bar suspension gives it handling that’s surprisingly capable for such a large car. Plus, the convertible top mechanism is robust and reliable.

What makes it perfect for Southern touring? It’s different enough to be interesting, reliable enough to be trustworthy, and cheerful enough to match the Southern hospitality you’ll encounter along the way.

Miles That Live in Memory

Here’s the real secret about classic car road trips in the South: it’s not really about the destination. Sure, Savannah is beautiful and New Orleans is legendary, but the magic happens in between. It’s pulling into a small-town diner and having three locals come over to talk about your car. It’s the way afternoon light hits chrome bumpers on a tree-lined highway. It’s discovering that 70 mph in a 1965 Impala feels completely different than 70 mph in anything built this century.

The South has the infrastructure for this kind of travel: gas stations that still provide full service if you ask nicely, mechanics who understand carburetors, and roads that were designed when cars had personality. You’ll find parts stores in small towns that still stock items for cars from the Johnson administration, and locals who remember when these cars were new.

Pack light, plan loosely, and remember that the best stories come from the unexpected detours. Your GPS might get you there faster, but your classic car will get you there with style. And in the end, isn’t that what really matters?