The 5 Best Classic Cars for the Great American Road Trip

Oldsmobile Vista Cruiser

Station wagons have fallen out of fashion and the Oldsmobile Vista Cruiser is one of those haulers that make me sad about the segment's demise. Sure, modern wagons are suitable for road trips too, but most of them are just hatchbacks with a slightly longer roof. The Vista Cruiser is downright massive at 18 feet long (5.5 meters) and not only it comes with an impressively spacious trunk, but also offers plenty of room in the second row.

Depending on which model and generation you go with, the Vista Cruiser can seat up to six people comfortably. You can actually buy a second-gen model with optional third-row seats, but you'll give up on most of the trunk. Speaking of which, the Olds wagon provides up to 100 cubic feet (2,831 liters) of cargo room, which is about 30% more than any modern minivan.

It's also twice as much as a modern full-size SUV like the Chevrolet Suburban. Sure, these massive haulers offer a bit more cargo space behind the front row, but it defeats the purpose of traveling with family and/or friends.

The Vista Cruiser debuted in 1964 and remained in production until 1977. It was powered by the brand's Rocket V8 engine exclusively, with displacements ranging from 330 to 455 cubic inches (5.4 to 7.5 liters). Output isn't an issue, even if you go with a late third-gen model from the Malaise era.

The Vista Cruiser is an affordable wagon. Prices usually vary from as low as $5,000 for examples in fair condition to around $25,000 for brilliantly restored units.

Chevrolet Suburban

While the Vista Cruiser isn't the most famous car out there, the Suburban is a freaking legend. Introduced in 1934 and still in production as of 2021, it's the world's longest-running nameplate. Essentially a station wagon body on the chassis of a small truck, the first-generation Suburban is perhaps the primordial proto-SUV.

While the early Suburban might not be ideal for long trips, later versions are as tough as they get and they can still run for decades with not a lot of maintenance. And some versions are off-road capable too, meaning you don't have to restrict your trips to highways and paved roads.

Picking a certain generation is probably a challenge because there are so many cool options out there. But this also means there's a solution for every taste. Be it the stylish fourth-gen version or the boxier seventh-gen SUV of the 1970s and 1980s, they're up for grabs in massive numbers on the used car market.

And just like the Vista Cruiser, the Suburban offers tons of cargo room, a spacious second row, and then some. And of course, you can always source a three-row model if your party involves up to nine people.

Prices vary greatly depending on generation and condition, but you can expect to find Suburbans from the 1960s to the 1980s with stickers ranging from $6,000 to $30,000.

Jeep Wagoneer

Of course the Jeep Wagoneer is on this list. It's one of the most iconic SUVs and, according to some, it's the nameplate that pioneered the premium hauler in the 1980s. But it's a completely different animal compared to the Suburban.

Introduced in 1963 by Kaiser Jeep, the Wagoneer soldiered on for almost three decades. And while it was constantly updated inside and out, the Wagoneer survived with the same underpinnings until 1991, when Chrysler decided to put an end to it.

But whether it's the early, bare-bones Wagoneer or the fancied-up Grand Wagoneer of the 1980s, this Jeep is as tough as they get with proper maintenance. And it will take you almost anywhere while also providing lots of room for passengers and luggage.

But unlike the Suburban above, the Wagoneer is a tad more expensive, with well-maintained examples costing as much as $25,000. Concours-ready model change hands for more than $50,000.

Ford Country Squire

But enough about SUVs. Let's get back to station wagons for a bit. The market was pretty much flooded with long-roof haulers back in the day, but the Country Squire is the one that stands out in my book. For one reason alone: the wood-grain body trim.

Yup, I'm a sucker for "woodie" designs, especially the first-gen Country Squire, which featured genuine wood body panels. Subsequent generations were fitted with wood-grain trim so they're not as authentic, but they are spacious and reliable. Perfect for that summer-long trip.

The Country Squier enjoyed quite a long life, with production stretching from 1950 to 1991 over eight generations. This means there are plenty of designs and an impressive variety of powertrains to choose from, including performance-oriented models from the muscle car era.

The Country Squire is just as spacious as the Vista Cruiser and nearly every generation offered a third-row seating option. In the 1960s, Ford even offered flat-folding rear seats facing toward the center of the cargo area, expanding seating capacity to 10 people.

With so many examples out there, the Country Squire can be had for as low as $12,000 in solid condition. A pristine example from the late 1960s won't cost you more than $25,000.

Buick Riviera

Wait, what? A two-door coupe on a list of wagon and SUV cruisers? Well, yeah, not everyone wants to do New York to Las Vegas in a long and heavy rig packed with suitcases and passengers. If your trip involves blasting "Bad to the Bone" through the speakers and your only companion is your better half, this one's for you.

Why not a Mustang or a Camaro you ask? Well, the Riviera is a full-size vehicle and provides significant luggage room in the trunk and even on the rear seats. After all, you can't take such a long trip empty-handed. What's more, the Riviera is one of the more premium full-size haulers from the 1960s.

And yes, I am talking about certain generations of the nameplate. The ones before 1974, when the once-stylish Riviera became a boxy, underpowered A-to-B car.

The first-gen model is arguably the Riviera to aim for. A unique appearance in the mid-1960s, it also came with a couple of high-power, Nailhead V8 engines. The second-gen (1966-1970) is almost as stylish and definitely more powerful, while the following generation is a solid choice if you like the boat-tail-style design.

Early Rivieras aren't very cheap though. While one in fair condition will set you back around $11,000, a nicely restored example will fetch more than $35,000.

That's it for my list. Which car would you take on a summer-long vacation and why? Would you opt for a vehicle that's not included here? Let me know in the comments section below.