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A woman leans out of an open car window, her long hair blowing in the wind
Bucket list

5 road trips to take once in your lifetime

By Anna Hart

April 2024

Feel the call of the open road? From an Arctic highway to a winding passage through the Japanese Alps, these bucket-list routes are sure to get your motor running

Driving the roads of a destination is a shortcut to its soul. And while some trips are strictly about stunning scenery, others offer an immersive experience, giving you a route into the region’s history, culinary heritage and architectural splendor. Here are five of our favorites.

The russet grasses, rough stone walls and rugged coastline of Inishbofin, Ireland
  • The mesmerising colors of Inishbofin, an island off the western Irish coast

The Wild Atlantic Way

Ireland


Tracing the western Irish coastline from northernmost Donegal to West Cork in the south of Ireland, the Wild Atlantic Way is 1,600 miles of dramatic scenery dotted with historic castle hotels, cozy traditional pubs, ancient Pagan sites and boat trips to otherworldly island monasteries.


As well as showcasing spectacular natural sights such as the Cliffs of Moher, the Wild Atlantic Way immerses visitors in Ireland’s maritime history at the town of Westport in Mayo, once home to Ireland’s pirate queen Gráinne O’Malley. You’ll also find medieval history among the dungeons and palatial grounds of Blarney Castle in Cork, and sacred sites such as the ruins of an Augustinian monastery on the island of Skellig Michael.

A view of islands, boats and the sea from a car driving Ireland's Wild Atlantic Way
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Tall trees and dramatic mountains as seen from the driving seat on the Dempster Highway, Canada
  • Find mountain adventure on the Dempster Highway

Dempster Highway

Canada


For dedicated road-trippers, Canada’s 458-mile Dempster Highway is the ultimate adventure, taking in quirky gold-rush towns as well as awe-inspiring Arctic scenery, luxury lodges, natural hot springs and a chance to see the northern lights.


Most drivers start off near Dawson City, a tiny town in Yukon Territory dubbed “the Paris of the North” at the peak of the Klondike Gold Rush in 1898. There you can stay in old clapboard hotels and drink at historic taverns, before touring the goldfields, and taking in the remote scenery at Tombstone Territorial Park. Then it’s out onto the open road, crossing the Arctic Circle and venturing onwards through the Mackenzie Delta to the town of Inuvik in the Northwest Territories.

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Cottages with pitched roofs, lush fields and steep forested slopes in the mountain village of Shirakawa-go, Japan
  • Storybook cottages in the mountain village of Shirakawa-go

Tokyo to Kyoto

Japan


Sure, you can zip between Tokyo and Kyoto on a two-hour bullet train, but road-tripping enables culturally curious travelers to explore the fascinating central region of Gifu, dubbed the Japanese Alps.


This under-visited but historically rich prefecture is home to the quaint mountain village of Shirakawa-go, the historic market town of Takayama (now filled with sake breweries and workshops, plus the Edo period Government House) and traditional ryokan stays in hot spring towns like Gero Onsen, a stone bath complex on the banks of the Hida River. The ancient samurai town of Matsumoto sits between Tokyo and Takayama, with its beautiful five-tiered Matsumoto-jō Castle.

The Pamir Mountains, Tajikistan, form a dramatic skyline that seems to go on forever
  • Central Asia’s stark mountain scenery feels otherwordly

The Silk Road

Central Asia


For two millennia, humans have traveled the trade network also known as the Silk Routes following the Great Wall of China from Xi’an, crossing the Taklamakan Desert, continuing into the Middle East and on as far as the Portuguese coast, through more than 40 countries.


Road-tripping the 168-mile section between Samarkand and Bukhara in Uzbekistan makes for an epic adventure. Tour the wonders of UNESCO-stamped Samarkand, then strike out on the M37 highway, passing Rabat-i-Malik caravanserai (one of the ancient hostelries); the 15th-century Ulugh Beg Madrassa (an Islamic school); and the 128-foot Vobkent Minaret (dating back to 1196), before rolling into Bukhara, the holiest city in Central Asia.

A man wearing an embroidered purple jacket and a hat with a large eagle perched on his hand; both look into the camera
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A red Fiat 500 drives through a stone archway in the tiny medieval hamlet of Lucignano d’Asso, Italy
  • The tiny medieval hamlet of Lucignano d’Asso

The Chiantigiana road

Italy


Famed for being one of the most scenic roads in Italy, the 37-mile Via Chiantigiana connects the ravishing historic cities of Florence and Siena, through rolling Tuscan hills, Chianti vineyards and picturesque villages and towns.


Famed as the cradle of the Renaissance, Florence is one of the world’s best city breaks for history-lovers, while end point Siena is UNESCO-protected and a medieval architecture gem. Tuscany is also, of course, famed for its food and wine—be sure to visit a vineyard and, in season, go hunting for truffles. History-rich pit stops include the delightful town of Greve, medieval Montefioralle nearby and the medieval fortress of Castellina in Chianti. 

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Photo of  Anna Hart
Anna Hart
Writer

Anna Hart is a culture writer specializing in adventure travel and positive-impact tourism. Her work has appeared in Vogue, The Wall Street Journal, and The New York Times, and she is the author of the travel memoir Departures.

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