Classic Destinations: These cars and places are a perfect match

Here at Hagerty, we believe that the best way to travel is by car. There is simply no better way to balance covering large expanses speedily, personal freedom, safety and flexibility than by car. And some destinations in particular demand a special car, especially if you want to magnify the event and drama. So for this piece we’ve done more than our usual twelve seconds of research to bring you some awesome road trip destinations and recommendations for the hardware that should get you there.

First, there are few destinations in the US as wonderful as a national park. So why not pack up a gorgeous 1941 Chrysler Town and Country Barrel-back Wagon and head for Jellystone Yellowstone NP to visit Yogi and Boo-boo? The season is perfect, the car looks appropriate both in town AND country and it’ll provide a nice, smooth Chrysler ride the entire trip. Just make sure to bring a pic-a-nic basket.

If your blood tends to run a bit hotter and you need more excitement than geysers and bears can provide perhaps a visit down south is more your speed. For this journey, the only real choice is a 1951 Hudson Hornet that won the 1951 and 1952 Daytona Beach Road Course Race (now Daytona 500). Driven by Marshall Teague, the Fabulous Hudson Hornet won the stock car race by over a minute both years, immortalizing the car and man. As an added bonus, driving on the beach (at certain times) is still permitted.

Daytona and its racing heritage are a blast but if you’re out west, then Bimmerfest is a little easier, logistically. This year it was held in the shadow of the Rose Bowl in beautiful Pasadena, CA. Of course you will need a BMW and we recommend the 1975 3.0CSi (or even better: a CSL). This was a car built for European touring car racing that can change direction more quickly and gracefully than a hummingbird—it’s engaging and truly telepathic. SoCal’s foothills beckon.

As it is summer, a drive to the beach is in order. Sunny Cape Cod is brilliant during the dog days and our car of choice would be the fun, little Fiat 500 Jolly. As unpretentious as it gets, the Jolly isn’t really designed for interstates but would excel as a Cape runabout. It doesn’t have doors or a roof beyond a flappy canvas/vinyl top and resembles a carnival ride more than a proper car. Who cares though, this car symbolizes a carefree, dolce vita.

Last, Bloomington Gold. If you don’t know what it is—picture Corvette heaven.  We recently featured a design analysis on the C2 Corvette, one of the most beautiful cars ever and certainly an appropriate choice. But as long as you’re driving a Vette, you really can’t go wrong. So for Bloomington Gold, how about you choose a 1968 Mako Shark Corvette, with a big block? It makes a much stronger statement than a C2 and it just devours the road. You could begin in Santa Monica, CA and trace Rt. 66 back up through the south- and mid-west to Illinois.