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On The Road

The World’s Most Scenic Coastal Drives

From Nova Scotia to New Zealand, eight great road trips with a sea view

  • Photograph by Mr Charles-Henry Thoquenne/Shutterstock

I grew up outside New York City, so my earliest road trips involved Interstate 95 and the New Jersey Turnpike, not exactly the sort of roads to inspire automobile wanderlust. As time went on, I came to explore and delight in more intimate byways in more inspiring places, from the American West to western Ireland via the South Island of New Zealand. For me, coastal routes hold a special appeal. Water vistas suggest a world that’s alive and constantly in flux, especially in contrast to the (relative) stability of the road and earth below it.

So, roll down the windows, breathe in the salt air and enjoy­ the ride on these eight routes.

Cabot Trail, Nova Scotia, Canada

  • Photograph by Mr Ériver Hijano

Cape Breton, the northern portion of the Canadian maritime province of Nova Scotia, is surrounded by water – the Gulf of St Lawrence, Cabot Strait, the open Atlantic and, at its heart, the brackish Bras d’Or Lake. The 185-mile Cabot Trail loop, which begins at the town of Baddeck, features heart-stopping coastal vistas while circling Cape Breton Highlands National Park. Minke and pilot whales can sometimes be spotted from lay-bys, but a summer whale-watching cruise from Ingonish will almost certainly produce sightings. If you’re a golfer, a stop here to play Highland Links is a must. There are many fine hikes along the Cabot Trail. The Skyline Trail, on the west side of the park, is a particular favourite. The fall foliage along the Cabot Trail can be brilliant, and visitors in early October can experience the many hues while celebrating the region’s rich Scots culture with the Celtic Colours Festival.

What to pack

  • Arc'teryx Cerium LT Quilted Ripstop Hooded Down Jacket

  • Albam Shetland Wool Sweater

Slea Head Drive, Ireland

  • Photograph by Offset

The Slea Head Drive (Slí Cheann Sléibhe in Gaelic) highlights the countless shades of green, among many other appealing features, of the western end of the Dingle Peninsula. Beginning in the town of Dingle, the 26-mile drive moves west, past Dunbeg Fort where the Atlantic crashes far below on the left and a sheer cliff rises vertiginously on the right. Further along, Slea Head offers faraway views of South Kerry and the Blasket Islands. The village of Baile an Fheirtéaraigh/Ballyferriter comes soon after, providing a perfect stop for a restorative pint and repast. There are many relics of early Christian structures along the drive, including Reasc Monastery, which dates back to the sixth century. Before heading south to Dingle, you’ll pass Cuas an Bhodaigh (Brandon Creek), believed to be the place where St Brendon the Navigator departed for points west in the sixth century, perhaps discovering North America en route.

What to pack

  • Brunello Cucinelli Quilted Shell Gilet

  • Loro Piana Mélange Baby Cashmere Rollneck Sweater

Acadia National Park Loop Road, Maine, US

  • Photograph by Mr Chris Bennett

Drivers enjoying the spectacular views of the Atlantic from the Acadia National Park Loop Road on the Maine coast have two early 20th-century titans to thank – industrialist Mr John D Rockefeller, who underwrote most of the project, and landscape architect Mr Frederick Law Olmsted, who helped design it. The 27-mile loop connects Acadia’s lakes, mountains, forests and rocky coast. Early risers who detour to the summit of Cadillac Mountain, the highest point along the US east coast, can be among the first to see the sunrise. A favourite stop is above Thunder Hole, a rock formation along Ocean Path where crashing waves reverberating within a small crevice create a suitably ear-splitting din. The loop passes Jordan Pond House, where you would be advised to partake of freshly baked popovers and Maine’s foremost export, fresh lobster. Locals prefer it simple, steamed in the shell with sides of melted butter and lemon.

What to pack

  • J.Crew Printed Mélange Fleece-Back Cotton-Blend Jersey Sweatshirt

  • Outerknown Paz Slim-Fit Organic Cotton-Twill Shorts

Overseas Highway, Florida, US

  • Photograph by Shutterstock

The Overseas Highway flows 113 miles in a southwesterly direction from below Miami to Key West, the southernmost point in the United States. It connects many of the islands, or keys, that make up the Florida Keys, with the help of 42 bridges, including the nearly seven-mile span of Seven Mile Bridge at Marathon Key. The deep blue and emerald green waters that frame much of the ride are a playground for divers, snorkellers, boaters and anglers. Detours from the highway may bring you in contact with some of the Keys’ unique flora, including a host of exotic birds and Key deer, a miniature species found only here. At the party town of Key West, you’ll encounter interesting two-legged fauna clutching Rum Runners and other cocktails as they the watch the sun plunge into the sea at the nightly Sunset Celebration at Mallory Square Dock. 

What to pack

  • Prada Camp-Collar Two-Tone Cotton-Poplin Shirt

  • Garrett Leight California Optical Club House 50 Aviator-Style Acetate and Gold-Tone Sunglasses

Ring Road, Iceland

  • Photograph by Gallery Stock

Iceland is a land of fire and ice, of stark, treeless landscapes and a rich mythical folklore. The Ring Road, all 82 miles, highlights many of its volcanically forged, glacier-filled wonders. And with such a spartan population, you’ll often feel that you have it all to yourself. Departing from Reykjavík, you could speed around the island in one long summer day, but most people take a week to appreciate the sights. A few must-linger stops include the Goðafoss waterfall east of Akureyri, which plummets 12m and is 30m wide, the glacier lagoon Jökulsárlón, where seals dodge chunks of glacial ice, the geysers in the Haukdalur Valley, the Great Geysir and Strokkur. Along the way, have a soak in one of Iceland’s many hot springs (the Secret Lagoon at Flúðir stays a constant 38 to 40°C). If anyone offers you hákarl, Iceland’s infamous fermented shark, you’d do well to politely decline.

What to pack

  • Moncler Empire K2 Panelled Quilted Shell Down Jacket

  • The Workers Club Ribbed Merino Wool Beanie

The Milford Road, South Island, New Zealand

  • Photograph by Mr Lukas Bischoff/Shutterstock

The Milford Road leads you on an unforgettable 62-mile journey through Fiordland National Park. After leaving the outdoor recreation hub of Te Anau along the shores of the lake, you’ll enter the Eglinton Valley, where snow-covered mountains rise dramatically from a lowland beech forest. You may recognise them from a certain movie trilogy. The Mirror Lakes are a valley highlight. On calm days, the Earl Mountains are reflected with eerie similitude. As you drop towards Milford Sound, you’ll pass through Homer Tunnel, a 0.75-mile-long passage that took 19 years to bore. After the tunnel, take a stroll to view The Chasm Falls, a complex of waterfalls carved by the Cleddau River. Soon you’ll reach Milford Sound, where cliffs rise abruptly from dark waters and mountains brush the clouds. If time permits, explore the sound from the water with a nature cruise or kayak trip, and then replenish yourself at The Blue Duck café and bar.

What to pack

  • Aspesi Distressed Denim Shirt

  • NN07 Marco Slim-Fit Stretch-Cotton Twill Chinos

Serra da Arrábida, Portugal

  • Photograph by Shutterstock

Arrábida Natural Park is less than an hour south of Lisbon, in a swathe of coastal land between the city of Setúbal and the small fishing village of Sesimbra. The road that follows the Atlantic through the park offers some of Portugal’s most pleasing ocean vistas, while the hills to the north provide a verdant counterpoint to the azure seas. The fine white-sand beaches along this stretch of coast are a favourite with Lisboetas. Stretch your legs, or go for a swim, at Portinho da Arrábida, where a sheltered cove and crystalline waters await. With a bit of advance planning, you can schedule a visit to the nearby Convento da Arrábida, founded by Franciscan monks in the 16th century. Or detour a bit inland to the town of Palmela to sample local vintages, including those made from the local Castelão grape, at Casa Mãe da Rota dos Vinhos.

What to pack

  • Loewe Striped Cotton-Jersey T-Shirt

  • Acne Studios Alvin Stretch-Cotton Twill Drawstring Shorts

Chapman’s Peak Drive, Cape Peninsula, South Africa

  • Photograph by Mr Charles-Henry Thoquenne/Shutterstock

Sandwiched between the near vertical cliffs of 593m-high Chapman’s Peak to the east and the crashing Atlantic to the west and punctuated by some 114 curves, Chapman’s Peak Drive (Chappies to locals) may be the most nail-biting and spectacularly scenic five-and-a-half miles in the world. The road begins at the picturesque fishing village of Hout Bay, just south of Cape Town, climbs to Chapman’s Point high above sandy bays before dropping to the artsy community of Noordhoek. Those wishing to stretch their legs can park and hike to Chapman’s Peak. From June to November, southern right and humpback whales can often be spotted from the road. There are lay-bys and viewpoints, but looking directly over the edge is not for those inclined to vertigo. Driving Chappies, one can’t help but marvel at its engineering. It took more than seven years to build.

What to pack

  • Theory Noland Suede Blouson Jacket

  • A.P.C. Pat Cotton-Gabardine Chinos

Road Trip Essentials

  • SAINT LAURENT Noe Washed-Canvas Backpack

  • Gucci Aviator-Style Gold-Tone Sunglasses

  • TOM FORD York Chain-Trimmed Suede Driving Shoes

  • Berluti + Native Union Leather-Trimmed Apple Charging Cable

  • Sisley - Paris Sunleÿa Age-Minimizing After-Sun Care, 50ml

  • Leica M240 Camera