Explore Italy with iBestTravel
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.
iBestTravel has created five different Italian itineraries, ranging from 5 to 10-day trips, covering the top cities, idyllic islands, and southern stretches of this beautiful country. If you have more time, slow down and add days at various stops, or combine multiple itineraries 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 abundance.
Venice: 2 days
With its achingly photogenic canals, stunning palazzi (mansions), and slender black gondolas, Venice gets you in the mood. If must-see places like Piazza San Marco, with its mosaic-encrusted basilica, and Palazzo Ducale are too crowded, seek out exceptional art in the 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 filled 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 2 km (1.2 miles) north of the train station. Besides the Torre, you can admire Pisa’s pristine 12th-century Duomo and the stubby, cupcake-like Battistero. Be sure to 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, 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 enjoy the vibrant 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. Here, you can experience electric street art alongside priceless artifacts from Pompeii at the Museo Archeologico Nazionale. Indulge in the world’s best pizza at one of the city’s many renowned pizzerias, and cap off your day 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, weaving 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 excesses of the Duomo and Leonardo da Vinci’s Last Supper, then explore contemporary art in a former distillery and browse designer styles in the boutiques of the Quadrilatero d’Oro. Enjoy a delicious risotto alla milanese (saffron and bone marrow risotto), and toast your journey 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, adorned with dazzling frescoes. You will also want to see Palazzo Te, a second Gonzaga palace 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 beautiful Lake Garda. Walk beneath the crenelated walls of the 13th-century Rocca Scaligera and enjoy lunch on a vine-covered terrace. Explore the impressive Roman ruins of Grotte di Catullo, then relax lakeside at Aquaria Thermal SPA.
Next 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 artistic treasures in the Museo di Castelvecchio and visit the city’s Roman Arena—catch an opera performance here if you are visiting in summer. Modern art awaits you 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 explore the trail-blazing designs of 16th-century architect Andrea Palladio. His masterpiece 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, visit Palazzo Leoni Montanari which houses 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 vibrant university city. Be sure to visit the Cappella degli Scrovegni, a northern Sistine Chapel showcasing a celebrated cycle of frescoes by Giotto. Afterward, you can learn about the city’s prestigious medical history at Musme and visit the magnificent Basilica di Sant’Antonio.
A Taste of Central Italy
Allow at least 7 days
Distance: 243km (150 miles)
Explore rolling hills crowned by medieval towns, verdant vineyards of the Chianti area, and Italy’s fourth-largest lake. Immerse yourself in classic Renaissance scenery on this tour through southern Tuscany and neighboring Umbria.
Florence: 2 days
Prepare for the journey ahead with a couple of days in Florence. Take in the Renaissance masterpieces of the Galleria degli Uffizi and the architectural wonders of the Duomo. Explore Piazza della Signoria, immersing in the vibrant street life, and meet Michelangelo’s David face to face.
Next stop: Drive 45 minutes from Florence to Chianti.
Chianti: 1 day
Dedicate day three to exploring the vineyards and wine estates of Chianti. Stop for a tasting at Greve in Chianti, the main town in the northernmost Chianti district, before enjoying a delicious steak lunch in Panzano and admiring contemporary art at Castello di Ama.
Next stop: Drive 1 hour from Chianti to Siena.
Siena: 1 day
With its medieval palazzi and striking Gothic architecture, Siena is a sight to behold in Tuscany. Climb the Torre del Mangia for panoramic views of the city and explore the beautiful Piazza del Campo, followed by a visit to Siena’s stunning 13th-century Duomo.
Next stop: Drive 1 hour from Siena to Lago Trasimeno.
Lago Trasimeno: 1 day
After four days on the road, take a mid-trip respite at Lago Trasimeno. The placid waters of Italy’s fourth-largest lake are soothing, especially when enjoyed from the medieval turrets of Castiglione del Lago, a laid-back town along its shores.
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. Navigate the historic, hilltop center and enjoy views of the Gothic cityscape. Stroll along Corso Vannucci and appreciate masterpieces in the Galleria Nazionale dell’Umbria, then visit Piazza IV Novembre and the Cattedrale di San Lorenzo.
Next stop: Drive 30 minutes from Perugia to Assisi.
Assisi: 1 day
Complete your journey with a pilgrimage to Assisi. This charming town is a major day-trip destination, centered around the Basilica di San Francesco, known for its stunning fresco cycle by Giotto. Below, the dimly lit lower basilica leads to St. Francis’ tomb.
The South Coast
Allow at least 7 days
Distance: 110km (68 miles)
From the hustle of Naples to the stunning seascapes of the Amalfi Coast, this premier summer tour combines world-renowned ancient ruins and classical art with breathtaking coastal scenery.
Naples: 2 days
Kick off your south coast adventure with a taste of urban energy in Naples. Explore Pompeiian mosaics and classical sculptures at the Museo Archeologico Nazionale, admire the Cristo velato (veiled Christ) statue at the Cappella Sansevero, and savor exceptional pizza in Spaccanapoli, the heart of the city’s historic center.
Detour: Follow the road west to uncover the Italian mainland’s first Greek settlement and one of the world’s most dangerous supervolcanoes in Campi Flegrei.
Next stop: Take a train from Naples to Pompeii (35 minutes).
Pompeii: 1 day
Catch the Circumvesuviana train and venture around the bay to Pompeii. This archaeological site offers a unique peek into an ancient city preserved by volcanic ash. Walk the streets and see the world’s first “Beware of Dog” sign as Mt. Vesuvius looms overhead.
Next stop: Take a train from Pompeii to Sorrento (30 minutes).
Sorrento: 1 day
Continue your coastal exploration in the sunny seaside town of Sorrento. Enjoy the vibrant streets, lovely bay views, and indulge in local ceramics and marquetry. Don’t forget to sample limoncello, a liqueur made from the region’s lemons.
Next stop: Take a boat from Sorrento to Capri (25 minutes).
Capri: 1 day
Capri, the most famous island in the Gulf of Naples, boasts breathtaking sights like the otherworldly blue light of the Grotta Azzurra (Blue Grotto). Roam around the ancient ruins at Villa Jovis, and for exceptional views, take the chairlift from Anacapri to the summit of Monte Solaro.
Next stop: Take a boat from Capri to Positano (30 minutes).
Positano: 1 day
The best way to reach Positano, the Amalfi Coast’s most enchanting and upscale town, is by sea. As you approach, notice the colorful houses cascading down the hills. Enjoy relaxation on the beach and stroll through vibrant streets, especially during sunrise or sunset.
Next stop: Take a bus from Positano to Amalfi (40 mins).
Amalfi: 1 day
Finalize your journey in Amalfi, the coast’s captivating capital featuring the striking Cattedrale di Sant’Andrea, charming ceramic shops, and a bustling seafront. Meander around sunny piazzas, or embark on a hike to take in more spectacular views.
Detour: Ascend to Ravello for stunning gardens and views (3 hours).
A Slice of Southeast Sicily
Allow at least 5 days
Distance: 297km (185 miles)
Between the black lava streets of Catania and the ancient Greek temples of Agrigento, this Sicilian itinerary showcases the island’s dramatic baroque beauty. Pass through a series of honey-hued towns nestled among citrus and olive groves paired with limestone cliffs and rugged canyons.
Catania: 1 day
Catania, dominated by Mt. Etna, is a stunning starting point. Enjoy the distinct black-and-white 18th-century architecture while savouring breakfast at Caffè Prestipino. Explore the famous fish market, La Pescheria, and don’t miss the breathtaking Chiesa di San Benedetto and the rooftop views from Chiesa di San Giuliano along Via Crociferi.
Detour: Weather permitting, hike to Mt. Etna’s crater summits with a guide.
Next stop: Drive 65 minutes from Catania to Syracuse.
Syracuse: 1 day
Syracuse, the birthplace of Archimedes, was once considered the most beautiful city in the ancient world. Today, it’s renowned for its stunning central square and magnificent Duomo, along with the intact 5th-century BCE Greek theater found in Parco Archeologico della Neapolis.
Next stop: Drive 40 minutes from Syracuse to Noto.
Noto: Half day
Noto is notable for its baroque architecture resulting from rebuilds after the earthquake in 1693. Stroll along Corso Vittorio Emanuele to admire the striking Cattedrale di San Nicolò, which shines in the evening sun.
Next stop: Drive 45 minutes from Noto to Modica.
Modica: Half day
Continue your exploration of Sicily’s baroque towns in Modica, famed for its artisanal chocolate. Visit Duomo di San Giorgio in Modica Alta, join locals for a passeggiata (stroll) on Corso Umberto I, and indulge in a delicious cannolo and unforgettable chocolate gelato.
Next stop: Drive 25 minutes from Modica to Ragusa.
Ragusa: 1 day
Head to Ragusa, featured in the acclaimed Inspector Montalbano series. Explore the historic center of Ragusa Ibla, where you will encounter rock-grey palazzi and Piazza Duomo, a well-known filming location. From here, stairs lead up to the town’s enthralling cathedral, the Duomo di San Giorgio.
Next stop: Drive 2.5 hours from Ragusa to Agrigento.
Agrigento: 1 day
Conclude your Sicilian journey in Agrigento, home to some of the most magnificent ancient Greek temples outside Greece. The highlight is the Tempio della Concordia, a standout in the sprawling archaeological park known as the Valley of the Temples.
