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The world's most iconic road trips

Angela Wood

Senior Contributor

The best way to see a new destination is undoubtedly by road. You can take a break to photograph places of interest, stay overnight wherever you desire, and visit legendary landmarks on route. Whether you’re hiring a Cadillac to cruise Route 66 with friends, navigating the winding cliffside roads of Italy’s Amalfi Coast, or travelling with a loved one along the Bavarian Romantic Road, here is our guide to the world’s most iconic road trips.

Amalfi Coast, Italy

As you traverse nerve-tingling winding roads, the Tyrrhenian Sea sparkles with a million diamonds and houses cascade down forested hillsides like pastel-coloured icing. As the Amalfi Coast is one of the most scenic coastal routes in Italy, you won’t want to miss a thing. From Sorrento, make your first stop at picture-postcard Positano with its luxurious cliffside hotels, secluded beaches and trattoria-laden piazzas or delve into history in the pretty maritime twin towns of Amalfi and Atrani. 

A rewarding hike along Sentiero degli Dei (Path of the Gods) gives you unrivalled vistas of the Bay of Salerno and is a great spot for a picnic and photography, or in Ravello, retreat to Hotel Villa Cimbrone, once a favourite of Salvador Dali, Virginia Woolf and Winston Churchill. While here, learn new culinary skills as you partake in a cooking class, wander through fragrant sculpted gardens or enjoy an excursion to discover ancient mosaics, hidden villas and frescoes of Pompeii, just 17 miles to the north.

Positano, Amalfi Coast

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Bavaria’s Romantic Road, Germany

As the name suggests, this route in Bavaria is one of Europe’s most romantic road trips – a magical land of half-timber villages, fairy tale castles, lush forests and meadows. The historic town of Rothenburg ob der Tauber, 45 miles south of Würzburg gives the illusion of stepping onto a Disney film set. Narrow cobbled streets, a year-round Christmas Museum and quaint, colourful houses only add to its allure. 

You can discover the country’s cloth trading history and walk ancient city walls in picturesque Dinkelsbühl or discover Nordlingen, a historic town of 20,000 people set inside a meteor crater! The architectural gem at the end of the Romantic Road is Neuschwanstein Castle which is said to have inspired Walt Disney’s Sleeping Beauty’s Castle. Surrounded by emerald forests, grand turrets and towers are highlighted against an Alpine mountain backdrop and crystalline cobalt lake. It’s a truly spell-binding location in which to conclude your Bavarian adventure.

Neuschwanstein Castle, Bavaria

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Miami to Key West, Florida, USA

It takes just over an hour to reach Key Largo at the northern point of the Florida Keys from Miami. The archipelago harbours every laid-back activity you could wish for, and each individual isle is unique. Key Largo is great for snorkelling, or if you fancy chartering a fishing boat for the day, Islamorada, the sports fishing capital of the world will tempt your adventurous spirit. 

Nature is on display in its finest form at Big Pine Key where you can happily spend an afternoon gliding through mangrove forests in a kayak, or if you wish to explore the history and nightlife of the Florida Keys, continue to Key West. Once home to Ernest Hemingway, Tennessee Williams and former US President Harry Truman, Key West inspires with conch-style houses, palm-lined boulevards and a buzzing atmosphere. It’s also the perfect departure point for a champagne sunset sailboat cruise so you can see the archipelago from a different perspective.

Islamorada Florida Keys

Credit: Kevin Ruck/Shutterstock

Cape Town to Port Elizabeth, South Africa

South Africa’s natural beauty is unashamedly on display on the drive between Cape Town and Port Elizabeth. The route is a magnet for nature and wildlife lovers and allows food and wine enthusiasts to sample innovative South African fare throughout their journey. Just 25 miles east of Cape Town, begin your adventure in Stellenbosch. The verdant wine region offers a variety of food and wine tours where you can sip delightful Bordeaux blends and tuck into award-winning cuisine on sun-kissed terraces overlooking the vineyards. 

Four hours along the road, Oudtshoorn – the ostrich capital of the world beckons. Stay a few days in the area and you’ll gain easy access to mysterious Cango Caves, Botlierskop and Buffelsdrift Game Reserves – home to the Big Five, plus, you can even enjoy a thrilling shark cage dive at Mossel Bay! 

A highlight of the drive for many is the coastal town of Knysna, dotted with art galleries, chic cafes and speciality shops. From here it's easy to reach the spectacular Map of Africa viewpoint in Wilderness, you can drive along the coast to chill with Capetonians in Plettenberg Bay or simply enjoy a tranquil sunset cruise on Knysna lagoon before continuing to Port Elizabeth.

Table Mountain Cape Town

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Great Ocean Road, Australia

The most scenic coastal drive in Australia can be navigated in a day from Melbourne, but if you wish to gain the most from this iconic route allow at least 3 to 4 days. Great Ocean Road was constructed between 1919 and 1932 as a memorial to fallen soldiers of World War I, and today it stretches 152 miles from surf resort Torquay in the east to historic Warrnambool to the west. A short drive along the coast from Torquay, you reach the pretty town of Lorne with horse riding, forest treks, kayaking and mountain biking to enjoy.

You’re almost guaranteed to spot cuddly koalas hugging branches of eucalyptus trees at Kennett River, or if you wish to seek out more Aussie natives, head for Great Otway National Park at Victoria’s southern tip. Home to 36 mammal species, you can catch glimpses of whales, dolphins, kangaroos and more. The main tourist highlights of the route are The Twelve Apostles - a collection of rugged limestone rocks jutting out of the sea at Port Campbell. They are best viewed at sunrise or sunset when you can avoid the tourist masses, alternatively, avoid people altogether by booking a private helicopter tour along the bay to see the Arch, Twelve Apostles and the Grotto all in one go!

The Twelve Apostles, Victoria, Australia

Credit: Dmitriy Komarov/Shutterstock

Route 66, USA

One of the USA’s legendary roads is Route 66. Small towns with attitude welcome travellers with kitsch souvenir shops, 1950s style diners and specialty museums which epitomise Americana. The entire route runs between Chicago and Los Angeles stretching in excess of 2,400 miles. However, if you can’t spare 3 weeks spare to drive across the country, you can focus on specific sections of Route 66 which incorporate highlights you want to see. The official route begins at Grant Park, Chicago. 

After a quick stop at Lou Mitchell’s by Union Station to stock up on silver dollar pancakes, root beer floats and doughnut holes for your 1950s style journey, head south to Springfield, Illinois and Mark Twain National Forest in Missouri. 

If you’re a collector of automotive memorabilia and enjoy discovering new artwork, focus your attention towards the painted murals of Cuba, Missouri and make a fun stop at Bob’s Gasoline Alley. Further south along the route, nature enthusiasts will appreciate the raw beauty of Route 66 in Arizona where the Painted Desert, Grand Canyon and Petrified Forest are easily accessible. Alternatively, drive from Oklahoma to see folk art at Ed Galloway’s Totem Pole Park or discover graffiti-covered vintage vehicles half-planted in the ground at Cadillac Ranch in Amarillo, Texas.

Bob’s Gasoline Alley Route 66

Credit: Nick Fox/Shutterstock

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