Jakki Phillips and Simon de Burton in their 1952 MG TD

There are many lessons to learn when taking part in your first classic car rally. The most important, I discovered when navigating on day one, is that 0.01 of a kilometre can mean the difference between a sizzling steak lunch with your fellow drivers at a charming hillside barbecue restaurant or a wrong turn, motorway mayhem and a rather dramatic police rescue.

My miscalculation occurred only four hours into Rally Nippon, which also happened to be my first outing in a vintage car. I was directing co-driver Simon de Burton along a quiet country road on the outskirts of Japan’s beautiful former capital, Kyoto, towards our lunch destination, which was up a side road. But I told him to turn a few metres too soon, sending us zooming off through tollgates onto a major highway rather than onto the street leading to the restaurant. With no exit for 15 kilometres, no U-turn permitted and our petrol gauge deep in the red, we were in trouble.

A camera-toting local snaps a 1952 AC Ace

Simon, a UK-based journalist and keen rally aficionado, pumped the brakes and expertly manoeuvred our 1952 MG TD into a lay-by before hopping out and scrambling up a steep, wooded embankment in search of help. Twenty minutes later he came running down the road with a dozen motorway police behind him—Simon clad in tweed jacket with neckerchief fluttering, they sporting bright-blue jumpsuits,  flags and whistles.

They spoke no English and we no Japanese, but the officers quickly realised our predicament. Through some enthusiastic semaphoring and a lot of shrill tooting to colleagues further up the road, they managed to stop the traffic and we were shepherded through an otherwise illegal U-turn, back through the tollgates and onto the right track to join our travelling companions.

Our drive of shame into the restaurant car park was met with sympathetic applause from our rally mates. They had even saved us a platter of skewers, which we devoured, and some strange snail-like sea creatures, which we did not.

The first day of the rally ended at Imabari Castle

I could blame my navigational gaffe on the fact we had no map, just a book of rules and directions written almost entirely in Japanese. Using GPS was also forbidden. But if truth be told, the explanation was less to do with my lack of experience and more to do with an excess of something else—hair. With the roof down, my unruly mane was plastered Wookiee-like across my face, making reading directions a tad tricky.

Which leads me to the second most important lesson: When racing in a convertible, take a leaf out of Grace Kelly’s style book and wear a head scarf. Not only will it bless you with the gift of sight—kinda handy when you’re navigating—but you’ll also avoid that “just been electrocuted” look when you step demurely from your vintage vehicle.

The Sakai brothers wore vintage motoring attire while racing their 1956 Porsche 356A Cabriolet

Thankfully, help was at hand from rally sponsors Dunhill, who presented me with a striped cashmere scarf that doubled up nicely as a head wrap. The British brand has been supporting the annual rally since its inception in 2009.

It’s a fitting partnership. Although best known today for its contemporary reimagining of traditional gentlemen’s attire, Alfred Dunhill founded the brand in 1896 as Dunhill’s Motorities in response to the growing popularity of the motor car. It promised “Everything but the Motor” and sold clothing, goggles and accessories such as horns and chauffeur jackets.

Functional gizmos such as headlamps no longer grace Dunhill’s shelves, but its quilted blouson jackets, silk pocket squares and suede driving shoes are still favoured by classic car owners keen to look good with the roof down. And Dunhill’s promotional campaigns still feature vintage models as handsome as the male ones.

A pale blue 1955 Porsche 356 Pre-A Speedster

Dunhill isn’t alone in its long love affair with British motoring; almost half the 70 cars entered in Rally Nippon were built in the UK, including two magnificent 1929 Bentleys (one a “Blower”), three Jaguar XKs, plus a Brit pack of Aston Martins, Triumphs, a Morgan and a Marcos 1500 GT. It was even a British car—a 1955 Austin-Healey 100 BN2 driven by Kamakura brothers Daisuke and Masamichi Okano—that won the rally.

Japanese marques were also out in force, with examples such as a 1970 Mazda Cosmo, a Toyota 2000 GT and a 1972 Nissan Skyline snarling alongside other crowd-pleasers from around the globe, including a 1928 Bugatti T37, a 1930 Talbot 90 Sport, a 1973 Ferrari Dino 246 GT, a 1957 Mercedes-Benz 300 SL Gullwing and a 1951 Opel Olympia.

Rally Nippon followed a picturesque 1,130-kilometre route, which started and finished in Kyoto

Our MG TD was lent to us by the rally’s founder, Yusuke Kobayashi, who inherited his enthusiasm for vintage cars and an extensive collection from his father. Kobayashi’s passion for the vehicles is surpassed only by his love for his homeland, and Rally Nippon serves as a fantastic showcase for Japan’s historic and cultural treasures.

While most of the rally participants are Japanese, Kobayashi’s goal is to attract more car connoisseurs from around the world. “We plan the route with great care as we want people to see a different side of Japan, to see its hidden beauty and experience our picturesque countryside—and, of course, sample our incredible food,” he says.

A 1957 Mercedes-Benz 300 SL Gullwing

The 1,130-kilometre route, which took us four days to complete, is indeed breathtaking. After setting off from the Toji Temple in the ancient city of Kyoto, we honked and waved our way through an ever-changing landscape, up misty mountains at daybreak and down through valleys dotted with tiny villages and farms, then cruised along the coast in the afternoon sun.

We journeyed onwards through Ehime, Kochi and Awaji Island, stopping at castles and temples along the way, many of them Unesco World Heritage sites. Camera-toting locals welcomed us with loud cheers as we approached each new destination.

A 1966 Marcos 1500 GT

The rally ended with a blessing at Kamigamo Shrine (another World Heritage site) in Kyoto—but, sadly, not for us. Which brings me to the final lesson of Rally Nippon—what to do when your engine blows up in the middle of a tunnel 100 kilometres from the finish line. Call your flag-waving, whistle-blowing, jumpsuit-clad friends in the local police force, of course, and head to the nearest inn for a large sake!  

 Rally Nippon is venturing further afield with its next rally, which takes place in Taiwan from November 10-13, starting and finishing in Taipei. The rally is open to a maximum of 70 cars, which must have been built before 1975. The entry fee is 550,000 yen. For more information, visit rallynippon.asia