Love classic cars? These are the most retro road trips on Earth

Nothing beats hitting the open road. There’s something undeniably romantic about watching a destination roll by — all on your own schedule — and if you’ve opted for a convertible, the age-old cliche of feeling ‘the wind in your hair’ can become an exhilarating reality.

Trend reports from the likes of Travelbag and Travel Tomorrow cite ‘slow travel’ as an enduring trend this year, where travellers take things a little more leisurely, focusing on the quality and depth of experiences rather than ticking off a list. Road trips are, perhaps, the ultimate way to slow down and take it all in, and what better way to do it than in a classic car?

According to Booking.com’s Travel Reinvented report for 2025, meanwhile, ‘vintage voyaging’ is on the up, whereby travellers ditch cookie-cutter experiences for more authentic ones, typically with a retro edge. Think rolling through rural France in a vintage Peugeot or touring the Highlands in an old-school Jaguar. Along with the trend for ‘set-jetting’ — seeking out the destinations of favourite books, films and series — travelling in a vintage set of wheels holds plenty of nostalgic appeal.

So, whether it’s winding through the hills of Tuscany or cruising along the California coast, we’ve picked seven road trips to inspire an adventure of your own.

1. Experience a touch of the Renaissance in Tuscany

Tuscany’s timeless landscapes dazzle with beauty of a Michelangelo painting. Florence is the inevitable starting point; the crucible of the Renaissance still glitters with cultural treasures, from the masterpieces that hang in the Uffizi to the soaring 15th-century Duomo. From here, Chianti spills out like a puddle of its namesake red wine, a region of rolling hills dotted with wineries and agriturismi (farmstays), many of them within easy reach of the handsome town of Greve in Chianti.

Head south east to the underexplored gem of Arezzo, or twist south on the Via Chiantigiana to Siena, famous for the Palio di Siena horse race, which thunders through the medieval streets twice each summer. South of here, the Val d’Orcia is Tuscany at its most painterly, all golden hills, cypress trees and spectacular hilltop towns like Montepulciano, Montalcino and Pienza, the last of those an UNESCO-listed example of Renaissance urban planning.

Rising to the north west is the hilltop town of San Gimignano, dominated by 14 towers once built by medieval nobles to flaunt their wealth. Pisa, towards the rugged Tuscan coast, needs little introduction for its own leaning tower, while the walled city of Lucca is a highlight of any Tuscan road trip, its rose-coloured piazzas the ideal spot to sip a glass of local lucchese wine. For literal immersion in the Tuscan countryside, however, drive north to Bagni di Lucca, a town renowned for its thermal waters and spa retreats, hidden away in chestnut forests.

The vehicle: Go for a slick ’50s Alfa Romeo Giulietta Spider or an old Fiat 500 for timeless Italian vibes, although the modern Fiat 500c convertible is an excellent choice. Alternatively, why not splash out on an Italian supercar — a Ferrari 296 or Lamborghini Aventador and the Tuscan tarmac are a match made in motoring heaven.

2. Live la dolce vita on the Bay of Naples

This is one of the world’s most spectacular drives; even slate-faced Roman emperors fell for the charms of the Bay of Naples and made their luxurious retreats here. A loop of the Sorrento Peninsula, just south of Naples, will prove the area has lost none of its cachet. Around every hairpin bend is scenery so spectacular — lemon groves, turquoise seas and sprawling, pastel-hued palazzi turned five-star hotels — you’ll think you’d stumbled onto the set of a Fellini film.

Start with a day’s discovery of Naples, an ancient city brimming with art and rugged elegance — perhaps with a visit to the Roman sites of Herculaneum or Pompeii, too — before heading to the coast. The peninsula is a straightforward drive with well-maintained but tight coastal roads. The SS163 threads along the southern edge, with plenty of options for stopovers: the lemon-scented lanes of Positano; Ravello, where fine dining at Rossellinis comes with jaw-dropping views; Atrani, with its famous beach; and Amalfi, whose glorious, wedding-cake cathedral towers above the picture-postcard town. Sorrento roughly marks a midway point on the drive — and is where boats leave for the glamorous isle of Capri, should you wish to rub tanned shoulders with the rich and famous — before the SS145 loops back towards Naples, with the great cone of Vesuvius brooding in the distance.

The vehicle: A retro Fiat 500 offers style and substance: these compact cars are ideal for navigating both the backstreets of Naples and winding coastal roads. A modern Fiat 500c convertible or Fiat Panda makes a good compromise. Consider an automatic, too, as the zigzagging coastal roads require plenty of clutch control.

3. Pop through the Champagne region

Vines have flourished in the chalk hills east of Paris since Roman times, and there’s no better way to explore than a languid drive along the Route Touristique du Champagne — a network of country roads connecting storybook villages and prestigious wineries. The elegant city of Reims makes an excellent introduction; with fine museums, bistros and a grand gothic cathedral, it merits a day’s exploration. In the neighbourhood of Les Crayères, many of the world’s finest marques have their houses, or maisons de champagne. Book ahead for tastings and tours at the likes of Ruinart, Taittinger and Piper-Heidsieck.

Further south — through the wine-growing districts of the Montagne de Reims and the Côte des Blancs, where hills are striped with vines of Chardonnay and Pinot Noir — the charming Grand Cru villages make worthy pit stops, including Le Mesnil-sur-Oger, Avize and Oger, their streets bedecked with flowers. The town of Épernay glitters with stately maisons, mostly along the Avenue de Champagne, where connoisseurs can take tours of the cellars at Moët & Chandon, perhaps the grandest of them all. History buffs, meanwhile, should detour to the village of Hautvilliers, the self-styled ‘cradle of Champagne’. It was within the hallowed walls of the abbey here that a monk named Dom Pérignon pioneered the production of Champagne at the turn of the 18th century.

Alternatively, strike out along the Marne Valley, another wine-growing district, for riverside picnics and walks through vineyards of Pinot Meunier, using the beautiful, spire-topped village of Aÿ-Champagne as a base.

The vehicle: A luxurious convertible feels fitting for a road trip exploring the world’s most prestigious tipple, so opt for something grand like the Jaguar F-type or Audi R8 Spyder. Or go vintage with a Citroën 2CV or Peugeot 404 — when parked up beside a rolling vineyard, it’s classic France at its best.

4. Cruise California’s iconic West Coast

The Golden State has enough variety for a lifetime, but California State Route 1 (SR-1) captures some of the best in a single trip, from lush vineyards to vibrant beach towns, with plenty of breathtaking coastal scenery.

From the surfing hotspot of San Diego, the road heads north as Interstate 5, before peeling away towards Huntington Beach, well worth a stop for its iconic pier and breezy West Coast vibe. Traffic around Los Angeles is inevitable, but make time to explore Santa Monica and Venice Beach, or take a spin around the mid-century mansions of Beverly Hills before curving north west to Santa Barbara, dubbed the ‘Californian Riviera’ for its balmy climate and laid-back lifestyle. It’s also here that the Santa Barbara Mission, a Franciscan monastery, has stood since 1786.

Also rich in 18th-century history is the town of San Luis Obispo, gateway to the sleek, modern wineries of the Santa Ynez Valley. It’s also a short hop to Hearst Castle, a 1920s-era, Mediterranean-inspired estate full of antiques and lavish interiors. As the road winds north towards Monterey, the stretch of coast known as Big Sur unfurls with jaw-dropping beauty, its rugged cliffs scored with redwood-backed coves. Enjoy the ocean vistas on the final leg to San Francisco, one of America’s most storied cities, renowned for its Victorian architecture and tram rides up hair-raisingly steep hills.

The vehicle: Powerful and stylish, Ford Mustangs or Chevrolet Camaros are made for the Californian tarmac. Evoke the Hollywood Golden Age with a more classic choice, such as a Cadillac Eldorado or a Chevrolet Impala, but consider the distances between stops when driving (the above trip is around 600 miles in total) – fuel efficiency and comfort are important.  

5. Drive Florida’s classic coast

The southernmost stretch of US Highway 1 (US 1) is Florida’s backbone, a 545-mile strip linking many of the Sunshine State’s top sights. Start on chic Amelia Island, home to luxurious hotels, golf courses and sublime Atlantic sunrises. It’s an easy drive from here to St Augustine, the oldest continuously inhabited European city in the US, rich with stately Spanish architecture.

At Daytona Beach, a sign modestly welcomes travellers to the ‘World’s Most Famous Beach’, though the days of motor racing on the sands are now an oil-slicked memory. The unspoilt beaches of Canaveral National Seashore, meanwhile, are a natural paradise, home to family-friendly swimming spots as well as mossy islets and mangrove forests at Mosquito Lagoon. The Kennedy Space Center looms large here, too; few fail to be awed by the scale of towering replica rockets, glittering IMAX films and exhibits on the history and future of space exploration.

Miami sizzles in the state’s south east, a hotspot for art and fusion cuisine. After soaking up the neon-splashed vibes at Miami Beach, pick up the US 1 through the Florida Keys, a chain of islands touching the tropics that’s all laid-back beach bars and coral reefs. Key West marks the southernmost tip of the ‘Lower 48’ states, and no trip here is complete without a piece of its namesake key lime pie.

The vehicle: A ’60s Ford Mustang is an iconic choice for American road trip — its chiselled chassis sparkles in the Florida sunshine — while the sleek Ford Falcon or Chevrolet Corvair are also some classic American ‘pony cars’. Modern Mustangs are smooth and powerful drives and offer more boot space and modern comforts such air conditioning, which is not always a given in the earlier generations.

6. Take a wild ride in Morocco’s Atlas Mountains

From otherworldly desertscapes to lush mountain gorges, Morocco rewards adventurous travellers, but it would be remiss not to discover Marrakech — a web of tranquil gardens, palaces and bustling, spice-scented souks make this one of the world’s most beguiling cities. From here, the N9 threads into the ochre foothills of the Atlas Mountains, and the drama of the Moroccan landscape reveals itself.

After Ait Ourir, the road snakes through the Tizi n’Tichka Pass, a route of plunging valleys and argan tree forests. Head east on the P1506 towards Telouet for the Glaoui Kasbah, a crumbling 19th-century fortress that evokes Telouet’s former days as a vital Saharan trading post. Refuel on traditional tagine at the town’s restaurant-auberge before winding on to Ait Ben Haddou, an ancient Berber ksar (fortified city) that rises on a rocky outcrop like a mirage. Film fans will recognise it as a backdrop from the likes of Gladiator and Game of Thrones, and a short drive away is the very ‘capital’ of Morocco’s film industry, Ouarzazate, home to studio tours as well as the rambling Taourirt Kasbah.

Head north east to take the R704 as it runs through the Dadès Gorges, a ribbon of dramatic, rocky canyons topped with fortresses. Birdwatching and scenic hikes are on the cards here; otherwise the village of Merzouga beckons to the east. Home to luxurious tented camps and the ‘sand sea’ of Erg Chebbi, it promises camel treks and unforgettable, violet sunsets over the dunes.

The vehicle: While a classic Jeep looks and feels the part for this rugged, sand-swept adventure, it’s generally easier to source a modern 4WD, such as a Hyundai Tucson, Volkswagen T-Roc R or Dacia Duster, which are well suited to both urban routes and rougher roads in more rural areas. 

7. Roll through Scotland in a Highland classic

Scotland promises some of Europe’s most epic landscapes, and its soothing palettes of greens, purples and earthy browns make a perfect foil to the bustle of its cities. Soak up the industrial and artistic heritage of Glasgow before taking the A82 north, skirting the bonnie banks of Loch Lomond, where eagles and ospreys wheel overhead. Luss, a picture-perfect village on the shores of the loch, is the ideal spot for lunch with a view, before a detour west to Inveraray Castle, one of the finest country piles in the land.

Further north, beneath the brooding peak of Ben Nevis, is Fort William, its stores and outfitters ideal for picking up supplies for hikes, cycles and watersports nearby. Head towards Mallaig for the ferry to the magnificent Isle of Skye, passing the iconic Glenfinnan Viaduct along the way, or take the sinuous A87 instead. A breathtaking drive, it winds past silent lochs, wide valleys and a scattering of ruined castles.

Back on the mainland, head east across the heather-flushed braes (hillsides) and pine forests of the Cairngorms National Park. This vast wilderness is the essence of Scotland: pebble-strewn rivers teeming with salmon, whisky distilleries and the rustle of a red stag on the moors. Take it slow and admire the scenery on the journey south to Edinburgh, Scotland’s handsome, lamplit capital, where royals, writers and rebels have shaped the streets for centuries.

The vehicle: For undisputed British elegance, go for a sporty Jaguar — the classic E-type, or a more recent XK — or an Aston Martin V8 Vantage, or DB6 for retro glamour. A Range Rover Evoque makes a brilliant choice, too, as much for its ability to handle tricky terrain as for its uncompromised style and comfort.