Top 10 Craziest Road Trips in Classic Cars

Check out this list of the ten craziest road trips taken in classic cars to get an idea of where you should go on your next trip and which car you should get.

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Check out this list of the ten craziest road trips taken in classic cars to get an idea of where you should go on your next trip and which car you should get.

From Route 66 here in the US to the Amalfi Coast in Italy and the coastline of Ireland, we’ve got you covered with some of the best road trips ever taken. To make them even better, each one is matched with the perfect classic car, from a 1965 Ford Mustang to the famous Aston Martin DB5.

Our goal is to provide you with the best, most helpful content possible, which means we typically like to talk about our own experience with topics. Sadly, I’ve never been able to take road trips like these in some incredible classic cars, but other people have. The trips below were all sent in from actual people who’ve made these drives in these cars, and then we tried to spin them in a way to put you and the rest of our readers right there in the driver’s seat.

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Ten Craziest Road Trips in Classic Cars

Embark on the adventure of a lifetime as you explore breathtaking routes and the thrill of driving a classic car. Each journey is tailored to give you a unique blend of challenges, scenic beauty, and the unmatched experience of cruising in a timeless vehicle.

1. Route 66: 1965 Ford Mustang

1965 Ford Mustang
1965 Ford Mustang

Imagine yourself behind the wheel of a '65 Ford Mustang – the quintessential American muscle car, cruising down the historic Route 66. The roar of its V8 engine echoes against the backdrop of the open desert.

This classic car, with its powerful performance and comfortable interior, makes tackling the long stretches from Chicago to Santa Monica a pure delight. As you navigate the old-school diners and motels, the Mustang offers the perfect blend of vintage style and robust engineering.

The Mustang's reliability and agility come in handy as you encounter various terrains on this iconic road trip. The lasting impression of the red-rock vistas, combined with the allure of the Mustang, encapsulates the spirit of American freedom.

Adventuring across Route 66 in a Mustang offers more than just a drive; it's a journey through time. Reflect on the historical significance of the Mother Road, while appreciating the timeless design and culture that the Mustang represents.

2. The Great Ocean Road, Australia: 1969 Chevrolet Camaro

1969 Chevrolet Camaro
1969 Chevrolet Camaro

The essence of 1960s American automobile artistry can be felt in every line of the 1969 Chevrolet Camaro. As you traverse Australia's Great Ocean Road, the Camaro's muscular presence and power match the untamed ocean waves crashing alongside the winding cliffside road.

The agility of this classic makes navigating the road's sharp twists and turns an exhilarating experience. With the Camaro's windows down, you'll absorb the salty sea air and the sounds of the coast, making for an unforgettable voyage.

The expansive windshield and comfortable seating in the Camaro allow for unobstructed panoramic views of the Australian coastline. The thrill of this road trip is not only found in the drive itself but also in the spellbinding landscapes that unfold around each bend.

Though the Great Ocean Road can be challenging, its allure lies in the unpredictable weather and the sheer beauty of the rainforests and ocean. Your Camaro doesn't just transport you; it becomes your companion on this journey of natural wonder.

3. The Amalfi Coast, Italy: 1957 Alfa Romeo Giulietta Spider

1957 Alfa Romeo Giulietta Spider
1957 Alfa Romeo Giulietta Spider

The winding roads of the Amalfi Coast call for a vehicle with allure and agility, much like the 1957 Alfa Romeo Giulietta Spider. With its lightweight design and responsive handling, the Giulietta Spider is the perfect match for the narrow lanes that curve around the Italian coastline.

As you grip the wooden steering wheel and shift through the gears, you'll feel a connection with the road that modern cars seldom offer. From the pastel-colored villages to the glimmering Tyrrhenian Sea, the Giulietta Spider gives you a front-row seat to one of the world's most picturesque routes.

Italian engineering shines in the way the car moves with almost intuitive grace, allowing you to savor every hairpin turn and coastal view. The open-top design invites the sun's warmth and the scent of blooming lemons, making your journey through Italy sensory-filled.

This classic Italian roadster, with its elegant lines and historic charm, not only complements the beauty of the Amalfi Coast but becomes an integral part of the experience, turning heads wherever you go.

4. The Scottish Highlands: 1962 Jaguar E-Type

1962 Jaguar E-Type
1962 Jaguar E-Type

Fasten your seatbelt as you embark on a journey through the Scottish Highlands in a car that Enzo Ferrari hailed as the most beautiful ever made – the 1962 Jaguar E-Type. With its sleek design and high-performance capabilities, the E-Type is an ideal companion for Scotland’s rugged terrain.

The car's 3.8-liter engine ensures a smooth yet lively ride through the glens and mountains, wrapping you in a symphony of engine notes only a classic can produce. Keep your camera ready, for every twist in the road offers panoramic views of Scotland's majestic natural tapestry.

In the E-Type, you’ll appreciate the perfect synthesis of power and elegance as you discover ancient castles and lochs. Even the unpredictable Scottish weather is no match for the excitement of the drive, with the E-Type’s snug cabin offering shelter.

Exploring the Scottish Highlands in the E-Type isn’t just about transport; it's about the joy of the journey and the timeless elegance that only this British classic can bring to such historic landscapes.

5. Pacific Coast Highway, USA: 1967 Chevrolet Corvette Stingray

1967 Chevrolet Corvette Stingray
1967 Chevrolet Corvette Stingray

The Pacific Coast Highway stretches before you, a ribbon of asphalt that demands a car with style and power, like the 1967 Chevrolet Corvette Stingray. With the Stingray's sculpted lines and raw power, you'll feel at one with this legendary American sports car as you cruise the California coast.

In the driver's seat of the Stingray, with the Pacific Ocean as your backdrop, freedom takes on new meaning. Its V8 engine and responsive handling make for an unforgettable drive through Big Sur and beyond, allowing you to embrace the essence of the American dream.

The Corvette Stingray, with its fiberglass body and cozy cockpit, ensures that each mile along the shoreline remains etched in your memory. Whether you're chasing sunsets or simply soaking in the vibrant coastal life, the Stingray makes every moment count.

Driving the Corvette Stingray on the Pacific Coast Highway isn't just a road trip; it's a statement of power and beauty, an experience that embodies the spirit of California's coastline.

6. The Romantic Road, Germany: 1955 Mercedes-Benz 300SL

1955 Mercedes-Benz 300SL
1955 Mercedes-Benz 300SL

Journey through the heart of Bavaria on the Romantic Road, in a car synonymous with German engineering – the 1955 Mercedes-Benz 300SL. As famous for its gullwing doors as for its racing pedigree, the 300SL lets you appreciate the fairy-tale castles and medieval towns in unparalleled style.

Each press of the accelerator immerses you deeper into the 300SL's world of luxury and performance. The car devours the miles between Würzburg and Füssen, showcasing its reliability and the precision that marks this route as a driver's paradise.

The Mercedes-Benz 300SL doesn't just handle the roads; it belongs to them. Its elegant curves and sleek bodywork are as much a part of the Romantic Road's scenery as the alpine landscapes and the historic architecture that lines this time-honored route.

With the 300SL, you engage with Germany's rich history from the unique perspective of a vehicle that itself is a piece of automotive heritage, ensuring every kilometer is driven with a sense of occasion.

7. The Garden Route, South Africa: 1960 Porsche 356

1960 Porsche 356
1960 Porsche 356

Imagine yourself cruising along South Africa's Garden Route in the sleek 1960 Porsche 356. This road is a spectacular stretch weaving between mountains, forests, and pristine beaches. You'd navigate the twists and turns with the Porsche's responsive handling, the flat-four engine's hum harmonizing with the calls of the wild.

In your journey, you face the thrilling challenge of managing the older, manual transmission through the route's elevation changes. Yet, every corner you conquer presents a new canvas of South African beauty—from the grandeur of the Outeniqua Mountains to the serene Knysna Lagoon—each view more astonishing than the last.

Taking the Porsche 356 along the Garden Route, you'd appreciate both the car's historical significance and its timeless design. On this road trip, it's more than just transport; it's a companion through the land's vast array of scenes. The verdant Tsitsikamma Forest and the rugged Eastern Cape Coast accompany you, as the Porsche's elegance becomes one with the diverse terrain.

The seamless marriage of the classic 356 style with South Africa's varied ecosystem encapsulates the essence of an unforgettable road trip. This Porsche carries you through an array of ecosystems, each reflecting a different shade of the 356's character—adventurous on the untamed coastlines, graceful along the delicate floral regions, and enduring against the backdrop of imposing cliffs.

8. The Ring Road, Iceland: 1963 Volvo P1800

1963 Volvo P1800
1963 Volvo P1800

Picture yourself navigating Iceland's majestic Ring Road in the reliable 1963 Volvo P1800. This route encircles the land of fire and ice, taking you past active volcanoes, blue icebergs, and steaming geysers. The Volvo's robust construction handles Iceland's unpredictable weather, keeping you secure amid the elements.

Your classic Volvo, stoic and sturdy, is confronted with the Icelandic terrain's challenges, from gravel patches to icy stretches. You're in for an immersive experience with your Volvo's intimate cockpit, providing a snug shelter as you observe the Northern Lights or the midnight sun through panoramic windows.

Circling Iceland, the P1800's elegance is matched by the raw beauty of powerful waterfalls and glacial rivers. This car, recognized for its role in "The Saint," imbues your journey with a sense of retro cool. It's a tasteful contrast to the rugged Icelandic landscapes, making every snapshot along the Ring Road feel like a scene from a vintage thriller.

Driving an iconic Volvo P1800 on this route, you forge a bond with the car as you both witness the grandeur of Mother Nature. The wild beauty of the Ring Road and the refined details of the Volvo—a juxtaposition of the untamed and the meticulously crafted—create the perfect setting for a road trip that's as crazy as it is beautiful.

9. The Transfagarasan Highway, Romania: 1970 Ford Escort RS1600

1970 Ford Escort RS1600
1970 Ford Escort RS1600

Envision the thrill of taming the serpent-like Transfagarasan Highway in Romania with the agile 1970 Ford Escort RS1600. As you scale the hairpin bends and rapid ascents, the Escort's rally-bred pedigree shines, with a balance of power and poise to master this challenging drive.

Your Escort faces a gratifying trial, harnessing its rally racing roots to navigate the tight turns and steep climbs. You grip the wheel firmly, the car responding energetically to each input, the Escort's racing history echoing with every bend in the road as you ascend to Balea Lake's glacial views.

The RS1600 is the perfect travel mate for vaulting the Carpathian mountains, its compact size slicing through the Transfagarasan's narrow sections. Each throttle blip and gear shift marries you closer to the Ford as if performing a duet with the road itself. Mountain fog veils ancient castles and thick forests unfold in your peripheral—the Escort's power plant singing through the valley.

Your journey with the Ford Escort RS1600 merges legend with landscape—the car's rally spirit daring you to push the limits while the Transfagarasan Highway dares to challenge even the bravest of drivers. This road trip is as much about discovering Romania's hidden treasures as it is about embracing the car's rich motorsport heritage.

10. The Wild Atlantic Way, Ireland: 1963 Aston Martin DB5

1963 Aston Martin DB5
1963 Aston Martin DB5

Take to the emerald shores of Ireland's Wild Atlantic Way in the classic 1963 Aston Martin DB5. Your drive is soaked in prestige as you grace the Atlantic coastline with the DB5, favored by none other than James Bond. Its six-cylinder engine purrs as you explore the rugged landscapes and ancient ruins.

On this wild Irish excursion, your DB5 meets the untamable Atlantic breeze, its steel integrity putting up a gallant fight against the coastal gusts. The route's secluded beaches and towering cliffs call for the Aston Martin's poised elegance, as you sip in the scenery just as smoothly as the car handles the winding roads.

You feel every inch the secret agent in the DB5 — each historical site and natural wonder a mission location as you delve into the heart of Gaelic culture. The Aston Martin is a beacon of sophistication, standing out against the raw coastal backdrops and charming villages that pepper your picturesque route.

In the Aston Martin DB5, the Wild Atlantic Way becomes an odyssey of luxury and discovery. The car's timeless appeal and Ireland's deep heritage create a road-tripping synergy that captures the essence of an enchanted journey, where legend and landscape collide.