Craft your ideal Italian getaway with these 5 amazing itineraries
Whether it’s your first trip to Italy or you're returning for more, designing the perfect itinerary involves selecting iconic sights you wish to see and hidden gems you want to discover.
We’ve put together five unique Italian itineraries, spanning 5 to 10 days, that highlight the top cities, picturesque islands, and the scenic south. Have extra time? Take it slow by extending your stay at various locations, or combine multiple itineraries for a memorable two-week or even three-week journey.
Discover the highlights of Florence, Naples, and Vatican City on this captivating Italy itinerary. Left, Shutterstock. Center, Getty Images. Right, iStock.Italy Highlights
Plan for at least 10 daysDistance: 930km (577 miles)
From the enchanting canals of Venice to the charming streets of Naples, this classic itinerary offers a quick introduction to Italy's must-see attractions. As you journey down the peninsula, you'll discover Roman relics, Renaissance art, baroque squares, and an abundance of delicious regional dishes.
Venice: 2 Days
With its irresistibly picturesque canals, magnificent palazzi (mansions), and elegant black gondolas, Venice sets the scene perfectly. If Piazza San Marco, featuring its intricate mosaic basilica, and Palazzo Ducale feel too crowded, explore exceptional artworks at Fondazione Querini Stampalia and the Peggy Guggenheim Collection. Browse seafood stalls at Rialto Market, enjoy drinks along Fondamenta dei Ormesini, and savor cicchetti (Venetian tapas).
Next destination: Board a train from Venice to Bologna (1.5 to 2 hours).
Bologna: 1 Day
Renowned as Italy's culinary hub and the location of Europe’s oldest university, Bologna boasts a beautifully preserved medieval center. Twenty towers rise above the red-brick centro, where streets are lined with porticoes filled with delis, bars, and trattorias. Don’t miss the impressive Basilica di San Petronio, the art at the Pinacoteca Nazionale, and the vibrant Quadrilatero district for dining.
Next destination: Catch a train from Bologna to Florence (40 mins).
Florence: 2 Days
Two days in Florence, Italy's unmatched Renaissance gem, may feel brief, but it offers a thrilling introduction to its iconic landmarks: the Duomo with its striking red-tiled dome; the Galleria degli Uffizi, housing one of the globe’s finest art collections; and, of course, Michelangelo's powerful David at the Galleria dell'Accademia.
Next destination: Catch a train from Florence to Pisa (1 hour).
Pisa: 1 Day
Travel west to Pisa to witness the famous Leaning Tower in person (hint: it really does lean). The Torre Pendente is the centerpiece of a trio of historic attractions at Piazza dei Miracoli, an elegant park-like square located 2km (1.2 miles) north of the train station. In addition to the tower, admire Pisa's immaculate 12th-century Duomo and the charming, cupcake-shaped Battistero. Don't forget to stroll along the city walls.
Next destination: Take a train from Pisa to Rome (3 hours).
Rome: 3 Days
The Eternal City, where all roads converge, Rome offers more than sufficient attractions to fill a lifetime. In just three days, you can explore must-see landmarks like the Colosseum, Pantheon, and Vatican Museums (home of the Sistine Chapel), while also enjoying the vibrant street life around Campo de' Fiori and wandering through the charming Trastevere district.
Next destination: Board 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 looming in the distance, Naples is vibrant, exhilarating, and utterly captivating. Where else can you experience striking street art alongside priceless artifacts from Pompeii at the ancient treasure-filled Museo Archeologico Nazionale? Indulge in the world’s finest pizza at countless beloved pizzerias. Conclude your day on a dramatic note with a performance at the historic Teatro San Carlo.
Explore the streets of Milan, trace Shakespeare's steps in Verona, and marvel at Padua's architecture on this northern Italy journey. Left, iStock. Center and right, Pete Seaward for Dinogo Planet.Majestic Northern Italy
Plan for a minimum of 6 daysDistance: 395km (245 miles)
Travel through northern Italy, soaking in noble villas and Renaissance art, reflecting on Shakespearean tales, and savoring acclaimed wines along the way. Starting in Milan, the route flows eastward, weaving through a series of historic towns towards Padua, nestled near the Venetian Lagoon and Adriatic Coast.
Milan: 1 day
Kick off your adventure in Milan, Italy's hub of fashion and finance. Be awed by the extravagant architecture of the Duomo and Leonardo da Vinci's Last Supper. Then, delve into contemporary art at a repurposed distillery from 1910 and explore designer boutiques in the Quadrilatero d'Oro. Indulge in risotto alla milanese (saffron and bone marrow risotto) and enjoy a canal-side aperitivo (pre-dinner drink) in the vibrant Navigli district.
Next stop: Drive 2.5 hours from Milan to Mantua.
Mantua: 1 day
Explore Mantua, a flourishing Lombard city celebrated for its Renaissance architecture and noble residences. The Palazzo Ducale, the grand home of the Gonzaga family, stands out with its stunning frescoes. Don’t miss the whimsical artistry at Palazzo Te, another Gonzaga palace often associated with romantic rendezvous.
Next stop: Drive for 1 hour from Mantua to Sirmione.
Sirmione: 1 day
Embrace the lakeside charm of Sirmione, located at the southern end of beautiful Lake Garda. Stroll beneath the fortified walls of the 13th-century Rocca Scaligera and enjoy lunch at a vine-covered terrace. Discover the remarkable Roman ruins of Grotte di Catullo, then relax by the water at Aquaria Thermal SPA.
Detour: Hike the trails around the mountaintop remains of Rocca di Manerba (2–5 hours).
Next stop: Drive 45 minutes from Sirmione to Verona.
Verona: 1 day
Spend your next day in Verona, the backdrop for Shakespeare's poignant play Romeo and Juliet. Explore the archaeological and artistic wonders at the Museo di Castelvecchio and visit the Roman Arena—if you're there in summer, don't miss an opera performance. For contemporary art, head to the Galleria d’Arte Moderna Achille Forti.
Next stop: Drive 50 minutes from Verona to Vicenza.
Vicenza: 1 day
Wander the streets of Vicenza to admire the groundbreaking designs of 16th-century architect Andrea Palladio. His masterpiece, La Rotonda, graces a hill overlooking the city, along with his stunning creations at Teatro Olimpico and Basilica Palladiana. For a change of pace, visit the baroque Palazzo Leoni Montanari, home to a remarkable collection of Italian art and Russian icons.
Next stop: Drive 45 minutes from Vicenza to Padua.
Padua: 1 day
Stroll through Padua, a vibrant university town. Don't miss its highlight, the Cappella degli Scrovegni, often dubbed the northern Sistine Chapel, renowned for its exquisite fresco cycle by Giotto—be sure to book your visit in advance. Afterward, delve into the city's rich medical heritage at Musme and visit the revered Basilica di Sant’Antonio where pilgrims gather.
Central Italy boasts the renowned wines of Chianti, the stunning architecture of Siena, and the medieval charm of Perugia. Left, Getty Images. Center, S.Borisov/Shutterstock. Right, Claudia Gori for Dinogo Planet.A taste of Central Italy
Plan for at least 7 days Distance: 243km (150 miles)
Experience rolling hills topped with medieval villages, lush vineyards of the Chianti region, and Italy’s fourth-largest lake. Immerse yourself in the timeless Renaissance beauty on this journey that winds through southern Tuscany and its neighboring Umbria.
Florence: 2 days
Prepare for your adventure with a two-day stay in Florence. Marvel at the Renaissance treasures housed in the Galleria degli Uffizi and the stunning architecture of the Duomo. Enjoy the vibrant street life around Piazza della Signoria and encounter Michelangelo’s iconic David up close.
Next stop: Take a 45-minute drive from Florence to Chianti.
Chianti: 1 day
Spend your third day exploring the vineyards and wineries of Chianti. Enjoy a tasting in Greve in Chianti, the main town of the Chianti Fiorentino region, then savor a prime steak lunch in Panzano in Chianti while appreciating contemporary art at the Castello di Ama.
Next stop: Drive for 1 hour from Chianti to Siena.
Siena: 1 day
With its medieval palaces and majestic Gothic architecture, Siena rivals any sight in Tuscany. For a panoramic view, ascend the Torre del Mangia, the elegant tower that rises above the Palazzo Pubblico and the sloping Piazza del Campo. Nearby, Siena’s 13th-century Duomo stands as one of Italy’s finest Gothic churches.
Next stop: Drive for 1 hour from Siena to Lago Trasimeno.
Lago Trasimeno: 1 day
After four days on the road, unwind at Lago Trasimeno. The tranquil waters of Italy's fourth-largest lake offer a peaceful retreat, especially from the medieval towers of Castiglione del Lago, one of the charming towns lining its shores.
Next stop: Drive 45 minutes from Lago Trasimeno to Perugia.
Perugia: 1 day
Next, visit Perugia, the regional capital of Umbria and a vibrant student hub. The ascent to the hilltop center may be steep, but the view of the Gothic skyline makes it worthwhile. Wander along Corso Vannucci and admire the treasures at the Galleria Nazionale dell'Umbria before relaxing at Piazza IV Novembre and exploring the Cattedrale di San Lorenzo.
Next stop: Drive 30 minutes from Perugia to Assisi.
Assisi: 1 day
To conclude your journey, make a pilgrimage to Assisi. This charming cobblestone town is a popular day-trip spot, centered around the impressive Basilica di San Francesco, a grand church complex featuring a renowned fresco cycle by Giotto in its upper church. Below, the dimly lit lower basilica, adorned with frescoes, leads to St Francis’ tomb.
Experience the highlights of Italy's southern coast with this itinerary featuring Capri, Pompeii, and Amalfi. Left, Getty Images/iStockphoto. Center, iStock, Right, Shutterstock.The southern coast
Plan for at least 7 daysDistance: 110km (68 miles)
From the vibrancy of Naples to the enchanting vistas of the Amalfi Coast, this 'best-of' summer journey showcases renowned ancient ruins and classical art, complemented by boat rides, island allure, and stunning coastal views.
Naples: 2 days
Start your adventure with the vibrant energy of Naples. Marvel at the Pompeiian mosaics and exquisite classical sculptures at the Museo Archeologico Nazionale, be sure to see the incredible Cristo velato (veiled Christ) statue at the Cappella Sansevero, and indulge in mouthwatering pizza in Spaccanapoli, the heart of the city’s historic center.
Detour: Venture west on a road trip to explore the Italian mainland's first Greek settlement and one of the globe’s most perilous supervolcanoes in the Campi Flegrei (consider adding an extra day).
Next stop: Catch a train from Naples to Pompeii (35 minutes).
Pompeii: 1 day
Hop on the Circumvesuviana train and journey around the bay to Pompeii. This remarkable archaeological site preserves the remnants of an entire ancient city frozen in time. Stroll along the streets and spot the world’s first 'Beware of the Dog' sign as the imposing Mt Vesuvius looms in the background.
Next stop: Take a train from Pompeii to Sorrento (30 minutes).
Sorrento: 1 day
Continue your adventure down the coast to the charming seaside town of Sorrento. While there aren’t many major sights, the joy lies in wandering the vibrant streets, soaking in the bay views, and exploring shops filled with ceramics and intricate marquetry. Don’t miss the chance to enjoy a shot of locally crafted limoncello, a liqueur made from juicy Sorrento lemons.
Next stop: Take a boat from Sorrento to Capri (25 minutes).
Capri: 1 day
Capri, the most renowned island in the Gulf of Naples, offers breathtaking sights. Marvel at the enchanting blue glow of the Grotta Azzurra (Blue Grotto) and explore the ancient ruins of Villa Jovis. For stunning coastal views, ride the chairlift from Anacapri to Monte Solaro, the highest point on the island.
Next stop: Take a boat from Capri to Positano (30 minutes).
Positano: 1 day
The best way to reach Positano, the most picturesque and upscale town on the Amalfi Coast, is by boat. As you near the shore, you'll see its colorful houses dramatically stacked on the hillside, creating a vibrant palette of peaches, pinks, and terracottas. Once on land, relax on the beach and wander its steep streets, which are especially delightful during sunrise or sunset, lined with trendy shops.
Next stop: Take a bus from Positano to Amalfi (40 mins).
Amalfi: 1 day
Welcome to Amalfi, the unofficial capital of the coast, featuring the stunning Cattedrale di Sant'Andrea, vibrant ceramic boutiques, and a lively waterfront. This compact town invites leisurely exploration through its sun-drenched piazzas or adventurous hikes.
Detour: Venture up to Ravello to admire its beautiful gardens and enjoy the finest views along the coast (3 hours).
Explore some highlights of Sicily with this itinerary centered on the southeast. Left, Shutterstock. Center, Getty Images. Right, Shutterstock.A glimpse into southeast Sicily
Plan for at least 5 daysDistance: 297km (185 miles)
Spanning from the dark lava streets of Catania to the ancient Greek temples of Agrigento, this Sicilian journey reveals stunning baroque architecture in the island's gourmet southeast. Along the way, discover a series of honey-colored towns nestled among citrus and olive groves, framed by limestone cliffs and rugged canyons.
Catania: 1 day
Overseen by Mt Etna, the baroque city of Catania is an inspiring starting point. Relish the town's unique black-and-white 18th-century architecture while enjoying breakfast at Caffè Prestipino on Piazza del Duomo, then explore the vibrant fish market La Pescheria. Be sure to visit the stunning Chiesa di San Benedetto and experience the exhilarating rooftop ascent at Chiesa di San Giuliano along the charming Via Crociferi.
Detour: If weather and volcanic conditions permit, embark on a hike to Mt Etna's four crater summits with a guide (allow for an extra day).
Next stop: Drive 65 minutes from Catania to Syracuse.
Syracuse: 1 day
Renowned as the birthplace of Archimedes (the mathematician famous for 'Eureka'), Syracuse was once hailed as the most beautiful city in the ancient world. Today, it continues to impress with its beautiful central square, Piazza del Duomo, and magnificent Duomo. Discover remnants from its early days, including the remarkably well-preserved 5th-century BCE Greek theater at Parco Archeologico della Neapolis.
Next stop: Drive 40 minutes from Syracuse to Noto.
Noto: Half day
The town of Noto is the first of three stunning baroque towns, all reconstructed after the earthquake of 1693. Noto shines as the highlight, featuring one of Sicily’s most beautiful streets, Corso Vittorio Emanuele, and the impressive Cattedrale di San Nicolò. This charming town radiates warmth in the soft glow of the early evening sun.
Next stop: Drive 45 minutes from Noto to Modica.
Modica: Half day
Continue the baroque journey in Modica, a once-thriving medieval town famed for its artisanal grainy chocolate. Seek out the Duomo di San Giorgio in the higher area, Modica Alta. Join the locals for a leisurely passeggiata (stroll) along Corso Umberto I; indulge in a cannolo filled with ricotta at Antica Dolceria Bonajuto and savor chocolate gelato at Caffè Adamo that you won't forget.
Next stop: Drive 25 minutes from Modica to Ragusa.
Ragusa: 1 day
Fans of the Inspector Montalbano series may recognize scenes from Ragusa. To explore these, venture to Ragusa Ibla (the historic center), where winding streets lead you past rock-grey palazzi to Piazza Duomo, a popular filming location. From this sun-kissed square, stairs ascend to the town's iconic cathedral, Duomo di San Giorgio.
Next stop: Drive 2.5 hours from Ragusa to Agrigento.
Agrigento: 1 day
Conclude your journey on a high note in Agrigento, renowned for its remarkable ancient Greek temples—the finest examples outside of Greece. The standout is the Tempio della Concordia, the main attraction in the Valley of the Temples, an expansive archaeological park that includes the remnants of the ancient city of Akragas.
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5/5