As the travel landscape of 2026 embraces the “Slow Travel” movement, a nostalgic revolution is taking hold on the world’s highways. Travelers are increasingly ditching modern SUVs for the mechanical soul of vintage wheels, seeking what National Geographic calls “Vintage Voyaging.” From the neon-lit stretches of America’s Mother Road to the sun-drenched, narrow hairpins of the Amalfi Coast, these retro road trips offer more than just a commute—they provide a sensory bridge to a more romantic era of exploration. Whether it’s the roar of a 1950s V8 in Havana or the rhythmic hum of a classic Fiat 500 in Tuscany, these journeys prove that sometimes the best way to see the future of travel is through a mid-century rearview mirror.
The Centenary Cruise: Route 66, USA
In 2026, the legendary Route 66 celebrates its 100th anniversary, sparking a massive “Retro Revival” across the American heartland. Oklahoma, which boasts the longest drivable stretch of the historic “Mother Road,” has become the epicenter of this celebration. To mark the centenary, the state has launched a dedicated “Neon Grant” program, helping historic diners and motels—like the iconic Wagon Wheel Motel—restore their vintage signage to their original mid-century glow.
For classic car enthusiasts, 2026 offers unparalleled events, including Tulsa’s Route 66 Capital Cruise, which aims to break records as the world’s largest parade of vintage vehicles. Driving a classic convertible through the flat prairies and red sandstone cliffs of Oklahoma allows travelers to experience “Americana” in its purest form. It is a journey defined by “faded Coca-Cola murals,” twirling barbershop poles, and the timeless lure of the open road that famously inspired Kerouac and Steinbeck.
La Dolce Vita: The Amalfi Coast, Italy
Nothing captures the cinematic elegance of the 1960s quite like navigating the Amalfi Coast in a vintage Fiat 500 or an old-school Alfa Romeo. The SS163 highway, which weaves along the southern flanks of the Sorrento Peninsula, is a masterpiece of engineering and aesthetics. In 2026, “Drive the Vintage” tours have become a staple for those looking to avoid the “cookie-cutter” tourist experience, offering travelers the chance to pilot these miniature icons through the narrow streets of Positano and Ravello.
The appeal of a classic car here is practical as well as aesthetic; the compact size of a retro Fiat is perfectly suited for the cliff-edged switchbacks that have captivated artists for centuries. Stopping at a roadside ceramic shop in Vietri sul Mare or enjoying a lemon granita in a sun-drenched piazza, travelers find that the car acts as a “cultural icebreaker,” inviting smiles and conversation from locals who view these vehicles as symbols of Italy’s enduring La Dolce Vita.
The Living Museum: Havana to Viñales, Cuba
In Cuba, the retro road trip is not a trend but a way of life. The island remains the world’s most famous “living museum” of 1950s automotive design, where Chevrolets, Buicks, and Oldsmobiles—locally known as almendrones—continue to serve as the backbone of daily transit. In 2026, National Geographic recommends a seven-day itinerary that starts in the Baroque streets of Havana and heads west toward the tobacco-rich valleys of Viñales.
Hiring a classic car with a local driver-guide offers a rare window into Cuban resilience. The journey through the Sierra del Rosario biosphere reserve to the “rainbow of Cuba” in Soroa is a masterclass in slow travel. Between sips of homegrown coffee and hikes through orchid gardens, travelers can discuss the complex history of the island with their drivers, making the classic car a vessel for “meaningful encounters” rather than just a photographic prop.
Alpine Elegance: The Dolomites and Tuscany, Italy
Beyond the coast, the rugged peaks of the Dolmites and the rolling cypress-lined hills of Tuscany offer two very different retro experiences for 2026. In the Dolomites, which will host the Winter Olympics later this year, touring in a vintage Jaguar or Porsche provides a high-performance thrill against a backdrop of “sculptural” limestone walls. The crisp mountain air and the scent of alpine wildflowers are best experienced with the top down, following the winding passes that connect hidden Ladin villages.
In contrast, the Tuscan “Strade Bianche” (white roads) invite a more leisurely pace. Navigating a vintage Peugeot or Lancia through the Val d’Orcia allows for spontaneous stops at family-run vineyards and medieval hamlets. This “Vintage Voyaging” trend highlights a desire for authenticity, where the mechanical quirks of a classic car encourage a deeper connection with the terrain—a reminder that the joy of the road trip lies in the rhythm of the drive, not just the destination.
The Great Atlantic Highway: Route 1, USA
While Route 66 owns the neon-tinged iconography of the West, Route 1 offers a “portrait of endurance” along the East Coast. Stretching 2,300 miles from the Canadian border in Maine to the southern tip of Key West, this road is a mosaic of fragmented paths and coastal vistas. In 2026, photographers and nostalgia-seekers are increasingly using vintage SUVs and station wagons to document the “weathering and slow decay” of the built environment against the relentless Atlantic waves.
The southern terminus in Florida remains a highlight for retro fans, where the Overseas Highway provides a surreal, water-bound driving experience. Watching the reflection of palm trees on the hood of a classic car while crossing the Seven Mile Bridge at sunset is a quintessentially American moment. As National Geographic notes, Route 1 is a road that “shifts with the light,” and there is no better way to witness its evolution than from the driver’s seat of a vehicle that has aged alongside the highway itself.
