Italy has more than its share of legendary drives. Many of the country's most spectacular routes are well traversed, first by the Romans and then by the subsequent civilisations and peoples who followed, carving out picturesque paths that offer much more than a means of getting from A to B. While some are particularly iconic – the well-trodden Amalfi Coast Road among them – there's plenty more to discover on your next Italian adventure, including one resident Italophile's dreamy tour of Franciscan monasteries in Tuscany. So fuel up and set off, allowing time to stop off for incredible meals, new encounters, and lots of snaps along the way.
Sicily
Approximate time: six hours
Start in the old, noble city of Palermo, where honey hues and crumbling stone splendour blur into a balmy labyrinth of restaurants and al-fresco wine bars. Dodge Vespas and zoom past old palazzos before heading west. Sip on cocktails at Trapani’s Scopello beach and marvel at the sandy meadows, olive groves and ancient columns of Agrigento further south. Then work your way up the east through Ragusa, Modica and Noto to Taormina, a dramatic town in the shadows of Mount Etna that’s home to an Ancient Greek amphitheatre and an annual film festival. Finally, hop on a boat to explore the sleepy Aeolian islands, where stretches of vineyards are peppered with white houses and craggy rock formations drop down into crystal-clear waters. Rosalyn Wikeley
Where to stay: Set in the Ragusan countryside a 35-minute drive from Sampieri, contemporary hotel Relais Chiaramonte offers a brief hiatus from baroque façades and frescoed ceilings.
Lausanne to Milan
Approximate time: four hours
Starting on the shores of Switzerland’s Lake Geneva and ending in Milan’s cobblestone streets, this rugged mountain tour is a cross-country extravaganza. The drive begins zigzagging around the hairpin bends of the Alps, through forested mountain trails and across the wine region of Chexbres before reaching the sleepy, medieval villages of Italy. Stop to explore the walled town of Ricetto di Candelo for family-run restaurants and panoramic views, or spend a day among the Belle Epoque villas of Stresa and the Borromean islands on the crystalline shores of Lake Maggiore. Round off the trip in Milan’s bohemian Brera district, where sand-hued buildings turn shades of orange and red in the light of the setting sun. Sophie Knight
Where to stay: Bulgari Milano, in downtown Milan. The hotel hosts fashion bashes showcasing the latest handbag or high-jewellery watch, the driveway is always nose-to-tail with blacked-out Bentleys, and all the best shops are in sight.
Tuscany
Approximate time: eight hours
This road-trip route zips in a figure of eight around Franciscan monasteries, Etruscan castles and medieval hamlets across Tuscany. Zoom down narrow streets watched over by coy Renaissance torsos, stopping off at cafés and wine bars to meet the locals – old ladies waving handkerchiefs, men sipping espressos at Formica tables. Outside Florence, hunt for truffles at Tenuta Torciano Winery, find restaurants hidden down driveways lined with cypress trees and explore walled cities behind sprawling vineyards and sun-kissed olive groves. Toby Skinner
Where to stay: Villa San Michele, once a Franciscan monastery, in the Fiesole hills overlooking Florence.
Bari to Salento
Approximate time: one-and-a-half hours
Puglia’s dry Salento region is the Italian answer to Cornwall – with its olive groves, cliff-jumping kids and unfussy cucina povera. Coastal roads run almost all the way around the heel, from the plunging limestone stacks and rocky bays of the outer east coast to the limpid tranquillity of the west coast, with white-sand beaches including the long and gloriously named Punta Prosciutto. At its core, Greek-influenced Salento is an escape – the opposite of a guided tour, it is a place of wild swims under limestone bluffs and open roads through the ochre landscape. Toby Skinner
Where to stay: Stay in the handsome town of Gagliano del Capo, where the converted 19th-century Palazzo Daniele is the smartest boutique hotel around.
Naples to Salerno
Approximate time: four-and-a-half hours
Yes, the drive from Naples' bustling heart to the historic port city of Salerno could take just an hour on a good day – but where's the adventure in that? Set off after a final carby feast (Naples is the home of the humble pizza, after all) and stick to the coastal road, passing first through Torre del Greco before swerving past Castellammare di Stabia towards the iconic Amalfi Coast towns via Sorrento. Stop for lunch or a bargain night's stay in one of the stunning Agriturismo spots such as Agriturismo Fattoria Terranova or Agriturismo Le Grottelle, or hold tight and splash the cash on a sunset supper-with-a-view in Positano or Amalfi. As the route takes in both iconic and underrated historical sites (Pompeii is a bucket list trip for many), this drive is best tackled over the course of a few days – especially as some of Italy's most exquisite hotels line the winding road. Connor Sturges
Where to stay: Le Sirenuse houses some of the most sought-after Amalfi Coast hotel rooms, with its rooms boasting unrivalled views of the sparkling Tyrrhenian Sea. Can't justify the expense? Swing by for an Old Fashioned in Franco's Bar and admire the scenery for a fraction of the price – no reservation required.