Italy Road trips

16 curated road trips in Italy — Amalfi Coast, The Dolomites, Chianti Road. Mapped stops, distance, duration, best season, and practical route notes.

These 16 routes range from 50 to 1610 km and from 1 to 10 days, across 1 country. Top picks: Amalfi Coast, The Dolomites, Chianti Road.

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  LegendaryAmalfi CoastItaly · 50 km · 3–5 daysThe SS163 may be the most beautiful road on Earth, hairpin bends cut into cliffs, pastel villages above an impossibly blue sea, lemon groves scenting the air.
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  LegendaryThe DolomitesItaly · 118 km · 2–3 daysThe Grande Strada delle Dolomiti, the Great Dolomites Road from Bolzano to Cortina d'Ampezzo through the most spectacular mountain scenery in the Alps. Huge cathedrals of rock, the Val di Fassa, the Sella Ronda massif, the Alta Badia, and vertiginous switchbacks between peaks of 3,168m and 3,218m.
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  IconicChianti RoadItaly · 71 km · 1–2 daysToscana simply doesn't get more bella than the SR222 through Chianti country, linking two great medieval cities through gently rolling countryside striped with cypress trees, olive groves, and vines. Most photogenic during the late springtime eruption of poppies and wildflowers; stop at every enoteca for Chianti Classico, a sangiovese-dominated drop that tastes like the landscape.
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  LegendaryStelvio PassItaly · 90 km · 1 dayOne of Europe’s classic alpine drives, the Stelvio Pass links Prato allo Stelvio and Bormio through a dramatic ladder of 48 switchbacks. Expect steep gradients, tight bends, soaring views, and a high-mountain atmosphere that feels especially memorable in clear summer weather.
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  NotableA Venetian SojournItaly · 186 km · 3–5 daysPink palaces, teal canals, golden domes, the Veneto is unlike anywhere else. From Venice's lagoon by vaporetto to Murano's glass furnaces, then on to the Brenta Riviera's Palladian villas, Vicenza's architectural masterpieces, and Asolo's hundred hilltop vistas.
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  NotableAbruzzo HighlandsItaly · 320 km · 3–4 daysItaly's most underrated region, the SS17 and mountain roads through the Apennine backbone past medieval hill towns, the wolf-and-bear wilderness of Gran Sasso, and a coastline that the Adriatic sun turns an extraordinary turquoise.
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  NotableEmilia-Romagna Food RoadItaly · 245 km · 3–4 daysAlong the Via Emilia, the Roman road built in 187 BC that still runs ruler-straight through Italy's gastronomic heartland from Parma to Ravenna. The route takes in Parma ham, Parmigiano-Reggiano, Modena's balsamic vinegar and tortellini, and Bologna's ragù, the most food-dense drive in the world.
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  NotableMille MigliaItaly · 1,609 km · 3–4 daysThe Thousand Miles, from Brescia south to Rome and back, run as a flat-out road race between 1927 and 1957 attracting 5 million spectators. Stirling Moss won in 1955 in a Mercedes-Benz 300 SLR at an average of just under 100mph, his co-driver reading instructions from an 18ft roll of paper. Today it survives as an annual rally for pre-1957 cars.
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  IconicSardinia Island LoopItaly · 1,500 km · 7–10 daysThe most rugged and authentic Mediterranean island, Cagliari's Phoenician quarter, the Barbagia highlands where banditry and ancient dialects survive, the nuraghe tower civilization's 7,000 bronze-age fortresses, Costa Smeralda's turquoise water, and Alghero's Catalan-speaking old town. Sardinia rewards the driver who leaves the coast for the interior.
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  NotableTarga Florio CircuitItaly · 108 km · 1–2 daysThe circuit of the Madonie mountains in Sicily was the world's oldest motor race, hairpins over sea views, Norman castles on hilltops, towns carved from golden limestone, and the most atmospheric mountain roads in Italy.
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  IconicThe Graceful Italian LakesItaly · 206 km · 3–4 daysFormed at the end of the ice age and a holiday destination since Roman times. Lake Maggiore's Borromean Island palaces, the cross-lake ferry to Laveno, then Lake Como, the siren call of Hollywood stars, traced from the silk capital of Como to Bellagio's perfect promontory and beyond to Bergamo.
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  IconicVal d'OrciaItaly · 90 km · 1–2 daysThe World Heritage-listed landscapes of Val d'Orcia have featured in Gladiator, The English Patient, and countless Renaissance paintings. Patchwork hills of cypress and wheat, walled medieval cities, Brunello di Montalcino paired with chestnuts and truffles, and the fortress of Radicofani at the end.
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  IconicWonders of Ancient SicilyItaly · 592 km · 7–9 daysThe most complete collection of Greek temples outside Greece, a UNESCO Roman villa of unrivalled mosaic floors, Baroque cities rebuilt after a 1693 earthquake, a Greek theatre overlooking an active volcano, and Mount Etna, all on the island that was the most fought-over piece of land in the ancient Mediterranean.
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  NotableSalento Coast, PugliaItaly · 117 km · 2–3 daysAlong the wild coastline of the Salento, the tip of Italy's heel in Puglia, from Otranto to Gallipoli along a jagged shore of sea stacks, hidden coves, and shimmering water in a hundred shades of blue. Prickly pears line the road; the finibus terrae (end of the world) is at Santa Maria di Leuca.
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  IconicShadow of VesuviusItaly · 90 km · 3–4 daysIn the shadow of the volcano that buried two cities in 79 CE, 90 km through Herculaneum's intact Roman houses, Pompeii's extraordinary preserved streets, the crater rim of Vesuvius itself, and Sorrento's clifftop lemon groves with the Amalfi Coast visible across the bay.
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  NotableSicily's SoutheastItaly · 71 km · 2–3 daysThrough Sicily's baroque southeast, Noto, Ispica, Modica, Ragusa, and Chiaramonte Gulfi rebuilt in Baroque splendour after the 1693 earthquake that levelled the region. The Cava d'Ispica gorge, grey drystone walls, citrus groves, and vivid Mediterranean colours in the sharpest light in Europe.