Whether it’s your first visit to Italy or you’re returning for more, building the perfect itinerary means choosing iconic places you want to see and under-the-radar destinations you want to explore.
We’ve created five different Italian itineraries, ranging from 5- to 10-day trips, covering the top cities, idyllic islands and southern stretches. Have more time? Slow down and add days at various stops, or add multiple itineraries together to create the perfect two-week or even three-week adventure.
Highlights of Italy
Allow at least 10 days
Distance: 930km (577 miles)
From the haunting canals of Venice to Napoli backstreets, this classic tour provides a whistle-stop introduction to Italy’s greatest hits. As you work your way down the boot you’ll encounter Roman ruins, Renaissance masterpieces, baroque piazzas and mouth-watering regional cuisines in spades.
Venice: 2 days
With its achingly photogenic canals, stunning palazzi (mansions) and slender black gondolas, Venice gets you in the mood. If must-see Piazza San Marco, with its mosaic-encrusted basilica, and Palazzo Ducale are too crowded, seek out exceptional art in Fondazione Querini Stampalia and Peggy Guggenheim Collection. Scour seafood stalls at Rialto Market, bar-hop along Fondamenta dei Ormesini and snack on cicchetti (Venetian tapas).
Next stop: Take a train from Venice to Bologna (1.5 to 2 hours).
Bologna: 1 day
Italy’s culinary capital and home to Europe’s oldest university, Bologna has a gloriously preserved medieval core. Some 20 towers loom over the red-brick centro, whose streets are lined with porticoes and crammed with delis, bars and trattorias. Check out the colossal Basilica di San Petronio, admire art in the Pinacoteca Nazionale, and chow down in the busy Quadrilatero district.
Next stop: Take a train from Bologna to Florence (40 mins).
Florence: 2 days
Two days is not long in Florence, Italy’s peerless Renaissance city, but it’s enough for a breathless introduction to its signature sights: the Duomo, with its famous red-tiled dome; the Galleria degli Uffizi, home to one of the world’s greatest art collections; and, of course, Michelangelo’s muscular David in the Galleria dell’Accademia.
Next stop: Take a train from Florence to Pisa (1 hour).
Pisa: 1 day
Head west to Pisa to see if the Leaning Tower really does lean (spoiler: it does, a lot). The Torre Pendente is the star of a trio of medieval sights on Piazza dei Miracoli, an elegant grassy square 2km (1.2 miles) north of the train station. Alongside the Torre, you can applaud Pisa’s pristine 12th-century Duomo and the stubby, cupcake-like Battistero. Squeeze in a walk along the city walls.
Next stop: Take a train from Pisa to Rome (3 hours).
Rome: 3 days
The Eternal City where all roads lead, Rome has more than enough to keep you occupied for a lifetime. In three days you’ll be able to visit headline sights like the Colosseum, Pantheon and Vatican Museums (home of the Sistine Chapel), while also having time to lap up the colorful street life around Campo de’ Fiori and explore the atmospheric Trastevere neighborhood.
Next stop: Take a train from Rome to Naples (1.25 hours on the fast train, 2.5 hours on the regular line).
Naples: 1 day
With Mt Vesuvius brooding on the horizon, Naples is fiery, fun and endlessly addictive. Where else can you pair electric street art with priceless finds from Pompeii in the ancient-treasure filled Museo Archeologico Nazionale? Gorge on the world’s best pizza in any number of popular pizzerias. End the day on an operatic high with a performance at Teatro San Carlo.
Northern grandeur
Allow at least 6 days
Distance: 395km (245 miles)
Cut a swathe across northern Italy, taking in aristocratic villas and Renaissance frescoes, contemplating Shakespearian drama and sipping cult wines along the way. From Milan the road winds east, passing through a string of historic towns en route to Padua near the Venetian Lagoon and Adriatic Coast.
Milan: 1 day
Start in style in Milan, Italy’s fashion and finance capital. Marvel at the architectural excess of the Duomo and Leonardo da Vinci’s Last Supper before perusing contemporary art in a former 1910 distillery and browsing designer styles in the boutiques of the Quadrilatero d’Oro. Dine on risotto alla milanese (saffron and bone marrow risotto) and toast the road ahead with a canal-side aperitivo (pre-dinner drink) in the Navigli area.
Next stop: Drive 2.5 hours from Milan to Mantua.
Mantua: 1 day
Embrace Mantua, a prosperous Lombard town renowned for its Renaissance architecture and aristocratic palaces. Chief among these is Palazzo Ducale, the vast residence of the Gonzaga family that ruled the city for centuries. Contemplate the Palazzo’s dazzling frescoes and compare them with the playful images that adorn Palazzo Te, a second Gonzaga palace that was often used for love trysts.
Next stop: Drive 1 hour from Mantua to Sirmione.
Sirmione: 1 day
Soak up lake life in Sirmione, on the southern tip of handsome Lake Garda. Walk beneath the crenelated walls of 13th-century Rocca Scaligera and lunch on a vine-covered restaurant terrace. Explore the impressive Roman ruins of Grotte di Catullo, then flop lakeside at Aquaria Thermal SPA.
Detour: Stride out on walking trails around the mountaintop ruins of Rocca di Manerba (2–5 hours).
Nex stop: Drive 45 minutes from Sirmione to Verona.
Verona: 1 day
Dedicate the next day to Verona, the setting for Shakespeare’s romantic tragedy Romeo and Juliet. Admire archaeological and art treasures in the Museo di Castelvecchio and go to the city’s Roman Arena – if you’re visiting in summer, catch an opera performance here. Modern art awaits in the Galleria d’Arte Moderna Achille Forti.
Next stop: Drive 50 minutes from Verona to Vicenza.
Vicenza: 1 day
Take to the streets of Vicenza to inspect the trail-blazing designs of 16th-century architect Andrea Palladio. His tour de force is La Rotonda, a villa on a hill overlooking the city, but you can also marvel at his work at the Teatro Olimpico and Basilica Palladiana. For a different style, the baroque Palazzo Leoni Montanari has a wonderful collection of Italian art and Russian icons.
Next stop: Drive 45 minutes from Vicenza to Padua.
Padua: 1 day
Amble around Padua, a rich, dynamic university city. Its star turn, for which you’ll need to book ahead, is the Cappella degli Scrovegni, a northern Sistine Chapel showcasing a celebrated cycle of frescoes by Giotto. Afterwards, you can bone up on the city’s prestigious medical history at Musme and join the pilgrims at the Basilica di Sant’Antonio.
A taste of Central Italy
Allow at least 7 days
Distance: 243km (150 miles)
Rolling hills crowned by medieval towns, verdant vineyards of the Chianti area and Italy’s fourth-largest lake await. Immerse yourself in classic Renaissance scenery on this tour that meanders through southern Tuscany and neighboring Umbria.
Florence: 2 days
Whet your appetite for the road ahead with a couple of days in Florence. Take in the Renaissance masterpieces of the Galleria degli Uffizi and the architectural splendors of the Duomo. Spend some time checking out the street life around Piazza della Signoria and go face to face with Michelangelo’s David.
Next stop: Drive 45 minutes from Florence to Chianti.
Chianti: 1 day
Dedicate day three to pottering about the vineyards and wine estates of Chianti. Stop off for a tasting at Greve in Chianti, the main town in the Chianti Fiorentino (the northernmost of the two Chianti districts), before lunching on prime steak in Panzano in Chianti and admiring contemporary art at the Castello di Ama.
Next stop: Drive 1 hour from Chianti to Siena.
Siena: 1 day
With its medieval palazzi and lordly Gothic architecture, Siena is a sight to compare with any in Tuscany. To admire it from above, climb the Torre del Mangia, the slender tower that soars over Palazzo Pubblico and the sloping Piazza del Campo. A short walk away, Siena’s 13th-century Duomo is one of Italy’s greatest Gothic churches.
Next stop: Drive 1 hour from Siena to Lago Trasimeno.
Lago Trasimeno: 1 day
After four days on the road, take a mid-trip time out at Lago Trasimeno. The placid waters of Italy’s fourth-largest lake are a soothing sight, especially if enjoyed from the medieval turrets of Castiglione del Lago, one of several laid-back towns draped along its shorelines.
Next stop: Drive 45 minutes from Lago Trasimeno to Perugia.
Perugia: 1 day
The next stop is Perugia, Umbria’s regional capital and a lively student city. It’s quite a climb to the hilltop center but worth the effort as the Gothic cityscape unfurls before you. Stroll Corso Vannucci and peruse the masterpieces of the Galleria Nazionale dell’Umbria before adjourning to Piazza IV Novembre and the Cattedrale di San Lorenzo.
Next stop: Drive 30 minutes from Perugia to Assisi.
Assisi: 1 day
To finish off, make the pilgrimage to Assisi. This small cobbled town, a major day-trip destination, is centered on the Basilica di San Francesco, a mighty church complex whose upper church shelters a celebrated fresco cycle by Giotto. Down below, the frescoed, dimly lit lower basilica leads through to St Francis’ tomb.
The south coast
Allow at least 7 days
Distance: 110km (68 miles)
From the tumult of Naples to the dreamy seascapes of the Amalfi Coast, this “best-of” summer tour offers world-famous ancient ruins and classical art accompanied by boat rides, island charm and breathtaking coastal scenery.
Naples: 2 days
Kick-off with a blast of urban energy in Naples. Feast your eyes on Pompeiian mosaics and stunning classical sculpture at the Museo Archeologico Nazionale, stop by to see the astonishing Cristo velato (veiled Christ) statue at the Cappella Sansevero, and tuck into to-die-for pizza in Spaccanapoli, the heart of the city’s historic center.
Detour: Hit the road west on a road trip to uncover the Italian mainland’s first Greek settlement and one of the world’s most dangerous supervolcanoes in the Campi Flegrei (factor in an extra day).
Next stop: Take a train from Naples to Pompeii (35 minutes).
Pompeii: 1 day
Catch the Circumvesuviana train and head round the bay to Pompeii. Italy’s most complete archaeological site is a unique place showcasing the remains of an entire ancient city caught in its death throes. Walk the city streets and see the world’s first “Beware of the Dog” sign as Mt Vesuvius looms menacingly on the horizon.
Next stop: Take a train from Pompeii to Sorrento (30 minutes).
Sorrento: 1 day
Continue down the coast to the sunny seaside town of Sorrento. There are few sights here; rather, the fun is hanging out on the colorful streets, admiring the bay views and browsing the stores selling ceramics and ornate marquetry. Knocking back a shot of locally made limoncello, a liqueur made from plump Sorrento lemons, is non-negotiable.
Next stop: Take a boat from Sorrento to Capri (25 minutes).
Capri: 1 day
Capri, the most famous of the islands in the Gulf of Naples. Here you can gasp at the otherworldly blue light of the Grotta Azzurra (Blue Grotto) and poke around ancient ruins at Villa Jovis. For magnificent seascapes, take the chairlift from Anacapri to the summit of Monte Solaro, the island’s highest point.
Next stop: Take a boat from Capri to Positano (30 minutes).
Positano: 1 day
The best way to get to Positano, the Amalfi Coast’s most Instagrammable and expensive town, is by sea. As you approach it, you’ll see its steeply stacked houses cascade down the hillside in a riot of peaches, pinks and terracottas. Once on dry land, hang out on the beach and stroll its vertiginous streets – a delight to walk at sunrise or sunset – fringed with voguish shop displays.
Next stop: Take a bus from Positano to Amalfi (40mins).
Amalfi: 1 day
The end of the road is Amalfi, the coast’s de facto capital with its striking Cattedrale di Sant’Andrea, colorful ceramic shops and busy seafront. It’s not a big place so you can take your time strolling around the sun-filled piazzas or taking a hike.
Detour: Head up to Ravello to check out its ravishing gardens and the best views on the coast (3 hours).
A slice of southeast Sicily
Allow at least 5 days
Distance: 297km (185 miles)
Stretching from the black lava streets of Catania to the ancient Greek temples of Agrigento, this Sicilian tour showcases spectacular baroque beauty in the island’s gourmet southeast. En route, pass through a string of honey-hued towns set amid citrus and olive groves shot with limestone cliffs and rocky canyons.
Catania: 1 day
Lorded over by Mt Etna, baroque Catania is an inspiring starting point. Soak up the town’s distinct black-and-white 18th-century architecture over breakfast at Caffè Prestipino on Piazza del Duomo and take a theatrical mooch around fish market La Pescheria. Don’t miss spectacular Chiesa di San Benedetto and the dizzying rooftop climb at Chiesa di San Giuliano on enchanting Via Crociferi.
Detour: Assuming the weather and volcanic activity is game, hike to Mt Etna’s four crater summits with a guide (factor in an extra day).
Next stop: Drive 65 minutes from Catania to Syracuse.
Syracuse: 1 day
Birthplace of Archimedes (the mathematician of “Eureka” fame), Syracuse was considered the most beautiful city in the ancient world. Still today, it’s a legendary looker with a stunning central square, Piazza del Duomo, and a magnificent Duomo. Remnants of its earliest days, including a magically intact 5th-century BCE Greek theater, can be found at the Parco Archeologico della Neapolis.
Next stop: Drive 40 minutes from Syracuse to Noto.
Noto: Half day
Noto comes as the first of a trio of baroque towns whose beguiling looks result from rebuilds after an earthquake in 1693. Noto is the belle of the ball, boasting one of Sicily’s most striking streets, Corso Vittorio Emanuele, and an eye-catching basilica, Cattedrale di San Nicolò. This beautiful town positively glows in the early evening sunlight.
Next stop: Drive 45 minutes from Noto to Modica.
Modica: Half day
Stick with the baroque theme in Modica, a once-powerful medieval town now best known for its grainy artisan chocolate. Search out Duomo di San Giorgo in upper town Modica Alta. Join locals for an afternoon passeggiata (stroll) on Corso Umberto I; buy a cannolo oozing ricotta at Antica Dolceria Bonajuto and chocolate gelato to die for at Caffè Adamo.
Next stop: Drive 25 minutes from Modica to Ragusa.
Ragusa: 1 day
Fans of the Inspector Montalbano hit TV series might recognize some places in Ragusa. To find these, head to Ragusa Ibla (the historic center) where labyrinthine lanes weave past rock-grey palazzi to Piazza Duomo, a frequent shooting location. From the sloping, sun-drenched square, stairs lead up to the town’s signature cathedral, the Duomo di San Giorgio.
Next stop: Drive 2.5 hours from Ragusa to Agrigento.
Agrigento: 1 day
Finish your tour on a high in Agrigento, home to a series of ancient Greek temples – the world’s finest outside Greece. Pick of the bunch is the Tempio della Concordia, the headline act in the Valley of the Temples, Agrigento’s sprawling archaeological park which encompasses the ruins of the ancient city of Akragas.
