Experience Italy from north to south in all its glory with this diverse 10-day self-drive itinerary. Tour Milan's magnificent gothic Duomo, sample Piedmont cuisine in Turin, visit the wine country of the Langhe region, and soak up the Renaissance atmosphere of Florence. Your journey ends in vibrant Naples, where you'll step back in time with a tour of ancient Pompeii.


  • Stroll the cosmopolitan streets of Milan
  • Explore the lush wine-growing region of Langhe 
  • See the Renaissance highlights of Florence
  • Step back in time at the Ruins of Pompeii

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Milan Milan
Day 2 Milan Sightseeing Milan
Day 3 Self-Drive Milan to Turin Turin
Day 4 Self-Drive in the Langhe Region Turin
Day 5 Self-Drive Turin to Florence Florence
Day 6 Florence City Tour Florence
Day 7 Self-Drive Florence to Viterbo Viterbo
Day 8 Self-Drive Viterbo to Naples Naples
Day 9 Private Tour of Pompeii  Naples
Day 10 Depart Naples  

Detailed Itinerary

Day 1: Arrive in Milan

Naviglio Grande canal in the evening
Evening on Milan's Naviglio Grande canal 

Welcome to Milan! Arrive at the Milano Malpensa or Linate airport, then transfer to the city center and check in to your hotel. Milan is known as the non-official capital of Italy, the place where everything happens. The city is a center for business, shopping, fashion, and culture, as well as medieval art and beautiful architecture.

Many of Milan's old monuments and buildings were destroyed during the Second World War bombings, and the new construction and modern architecture give Milan a sophisticated vibe. Because of this, Milan is known as Italy's "new" city and represents modern Italy. 

Many of Milan's famous historical sights are clustered together in the heart of the city with easy access from the train station, so it's easy to explore on your own today while you get acquainted with the city. Top sights include the striking Gothic Duomo, La Scala Opera House, Galleria Vittorio Emmanuele (a glamorous 20th-century indoor shopping mall), the Pirelli Tower, and the medieval Castello Sforzesco. Milan is also home to one of the world's most famous paintings—da Vinci's The Last Supper, housed at the Santa Maria della Grazie monastery. 

If there's enough time in the afternoon, a stroll through the downtown district is an excellent way to spend the day. A visit to the 16th-century Royal Palace, a sprawling neoclassical palace turned art museum, provides a perfect introduction to the city's history and art. Although the building suffered great damage during World War II, it has been beautifully restored and is now a renowned cultural center. 

In the evening head to the Navigli at Porta Genova, Milan's ancient network of canals and passages used for transporting goods and supplies across the city. At night these streets transform with crowds of locals and tourists meeting friends at bars and restaurants. Come for the buzzing energy, stay for the wine bars and people watching.

Day 2: Milan Sightseeing

Sightseeing in Milan's city center

Today you'll meet your English-speaking guide at the lobby of your hotel for a three-hour sightseeing tour of Milan. Sights will include closer looks at the colossal and flamboyant Milan Cathedral, La Scala Opera House, and the Castello Sforzesco. The Castello houses municipal museums devoted to Egyptian and other antiquities, musical instruments, paintings, and sculptures. Highlights include the Salle delle Asse, a frescoed room attributed to Leonardo da Vinci, and Michelangelo's unfinished Rondanini Pieta.

In the afternoon you are free to explore Milan on your own. Follow the famous quadrilatero della moda from Via della Spiga to Via Montenapoleone to immerse yourself in some shopping or head to the Brera district to try out a local osteria or trattoria for dinner. Milanese food is quite rich and luxurious and known for delicious risottos. 

Day 3: Self drive Milan to Turin

Elegant architecture in Turin

After one last cappuccino in an open-air cafe. head to the rental station to pick up your car and hit the road to Turin

En route, we suggest detouring an hour north for a quick visit to the picturesque Lake Como. One of the three main lakes in Italy's Lake District, alongside Lake Garda and Lake Maggiore, Lake Como is grand yet peaceful and quiet, surrounded by forests that add to the serenity. The lake is popular with travelers from around the world and has attracted numerous celebrities who own villas along its shores, including George Clooney and Madonna.

After a leisurely lunch, gelato, and a walk along the lakeside promenade, it's time to get back on the road and continue the two-hour drive through the Piedmont region to Turin, a city famous for its sophisticated and historic architecture, museums, and food (notably chocolate). Set against a backdrop of the towering Alps, Turin remains one of Italy's most fascinating cities, named in the New York Times "52 Places to Visit" in 2016. 

After settling into your hotel, you're free to explore the city. Start with a visit to the historic center with its many interesting monuments, or walk across the river over the Ponte Vittorio Emanuele I bridge to the Santa Maria del Monte dei Cappuccini church. The walk is uphill but not steep, and you'll be rewarded with panoramic views across the entire city.

History lovers can head to the Turin Egyptian Museum for a self-guided tour, or stop by the Parco Archeologico Torri Palatine to see the Palatine Towers, the world's best-preserved Roman city walls from the 1st century. If there's time, stop off at the Parco del Valentino for a late afternoon stroll through the sprawling medieval riverside park. Check out the replica medieval village, then walk over to the hip San Salvario neighborhood for drinks at an aperitivo bar before dinner. 

Day 4: Self-Drive in the Langhe Region

Lush vineyards of the Langhe Region
Lush vineyards of the Langhe region

Today is yours to explore the beauty of the local Langhe region by car. Just 37 miles (60 km) south of Turin, the Langhe is an extraordinary wine district rich in noble vineyards, exceptional sceneries, ancient castles, and outstanding cuisine. Some of Italy’s greatest wines are produced here, including Barolo, Barbaresco, and Nebbiolo. 

Consider a lunch stop in the town of Bra, at the restaurant where the Slow Food Movement was born. The movement was started by Carlo Petrini and a group of activists in the 1980s with the aim of defending local culinary traditions, access to clean food, and a slower pace of life. Feast on local specialties, from bagna cauda (Piedmontese for "warm sauce" prepared with olive oil, garlic, and anchovy paste) to agnolotti (egg pasta stuffed with roast meat) and tajarin (the local word for thin egg noodles). Round out your meal with a hearty risotto and brasato al Barolo (stewed for hours in the famous wine), then finish with a sweet treat: gianduiotto, a combination of sugar, cocoa, cocoa butter, and the Tonda Gentile hazelnut.

Other highlights of the region include:

  • In Barolo, visit the Castello Falletti with a small museum inside and the Enoteca Regionale del Barolo (a large collection of Barolo wines where you can taste and purchase your favorites).
  • Monforte d’Alba has a few historic monuments to visit including the Palazzo Scarampi, with an ancient amphitheater, and the 17th-century church of Sant’Agostino and San Bonifacio
  • La Morra is a larger village with a square, Piazza Castello, in the center, which has great views over the vineyards. You can also visit the Church of San Sebastiano, climb the baroque style Torre Campanaria di La Morra (the tower of La Morra), and see the Church of San Martino at the top of the village.

As the sun sets over the hills, it's time to head back to Turin for the evening.

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Day 5: Self-Drive Turin to Florence

Blue skies over the Duomo di Firenzi

After enjoying a relaxing breakfast at your hotel, you'll head south again for today's 4.5-hour drive to Florence.

On the way, you may wish to stop in Parma, a city famous for its ornate medieval architecture, the beautiful countryside, and, of course, the food. Points of interest include the 10th-century University of Parma, the Museo Glauco Lombardi, which documents the life of Maria Luigia, and the Piazza Duomo, where you'll find the city's cathedral and baptistry, both from the 12th century. 

After arriving in Florence, check into your hotel and spend a leisurely afternoon exploring the city. Long considered a cultural capital and the "Jewel of the Renaissance," Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo and the Galleria dell'Accademia

Other top sites include the Piazza della Repubblica, one of the city's main squares that's marked the city center since Roman times. The Piazza della Signoria, the city's political center since the Middle Ages, is where ceremonial events, rallies, and festivals are celebrated. Here you'll find two iconic Florentine landmarks—Palazzo Vecchio and the Uffizi Gallery, which houses works by Michelangelo and Leonardo da Vinci. The square's centerpiece is the Neptune Fountain, a popular meeting place. 

Another highlight is Ponte Vecchio, a covered medieval bridge that's been a symbol of Florence's power for over seven centuries. The bridge houses buildings and shops, which have been occupied by merchants and shopkeepers since the Middle Ages. A short walk away, the Italian Gothic Cathedral of Florence and Giotto's Bell Tower rise above the surrounding city buildings.  

In the evening, enjoy some gelato and people-watching, followed by dinner and drinks at a local restaurant.

Day 6: Florence City Tour

Florence's Famous Ponte Vecchio Bridge
Florence's famous Ponte Vecchio bridge

Spend today exploring the city's top sites, starting with a guided half-day walking tour. Stops include the iconic Duomo, with its terracotta-tiled dome, the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture, and the San Lorenzo Church, the former parish church of the powerful Medici family. 

Your afternoon is free to explore some of Florence's other notable attractions and highlights. Recommendations include:

  • Spend some time learning about Florence's history in the Basilica di Santa Croce history museum.
  • Explore science and art at the Museo dell'Opera del Duomo (history and art museum) and the Museo Galileo Institute and Museum of the History of Science. 
  • Visit the Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years.
  • Shop for hidden treasures and your lunch special in the San Lorenzo market.
  • Head to the south bank of the Arno River to the Piazzale Michelangelo viewpoint for panoramic views of the city.
  • Stroll through the peaceful and relaxing greenery of the Boboli Gardens.

Celebrate your last evening in Florence by stopping off at bar SESTO, close to the Ponte Vecchio bridge, for a pre-dinner cocktail on the terrace while you enjoy the sunset, then make your way to the hip Sant'Ambrogio neighborhood for dinner accompanied by a glass of Tuscan wine.

Day 7: Self-Drive Florence to Viterbo

Drive through the hill towns of Umbria and Lazio

Today you'll leave the Cradle of the Renaissance and drive 2.5 hours south to the northern Lazio town of Viterbo, home to the largest medieval historical center in Europe.

Viterbo and Upper Lazio are characterized by a landscape of volcanic origins, with the lakes of Bolsena and Vico formed from ancient extinct craters. Founded by the Etruscans and later taken over by the Romans, Viterbo developed into an important medieval center, and in the 13th century was briefly the seat of the papacy. It was heavily bombed in WWII, but much of its historic core survived and its attractive tangle of grey-stone buildings remains in remarkably good shape. 

On the way, consider a lunch stop in Orvieto, a famous village perched on a plateau overlooking local vineyards and offering spectacular views of the surrounding hills of Umbria. Orvieto is known as a "stratified city" where Etruscan ruins collide with the stunning remains from the Medieval and Renaissance periods. Highlights include the Pozzo di San Patrizio, a historic well and engineering marvel that was designed to obtain water from the depths of the bluff it sits on. From there, venture to the edge of town and walk along the city walls to take in your beautiful surroundings in this enchanting place.

Day 8: Self-Drive Viterbo to Naples

Explore the vibrant neighborhoods of Naples

Bid Viterbo farewell this morning and hit the road for a 3.5-hour drive to Naples. Set on the picturesque Bay of Naples near the still-active Mount Vesuvius, Naples has been continually settled for millennia and is renowned for its art, architecture, and religious frescoes. 

On the way, you can stop in Caserta for a quick tour of the famous Reggia di Caserta, an 18th-century Baroque palace located near Naples. The UNESCO World Heritage site is one of the many jewels in Italy's southern Campania region and is well worth a visit for its architectural grandeur and rich history. Constructed for the Bourbon king of Naples, it was modeled after the Palace of Versailles and is the largest royal residence in the world. 

After arriving in Naples and settling into your accommodation, make the most of your time in the coastal city with some sightseeing: 

  • Visit the Naples Archaeological Museum to see Roman, Greek, and Renaissance-era ruins, including artifacts from nearby Pompeii.
  • Tour the Castel dell'Ovo, a seaside castle located on the former island of Megaride.
  • See the 16th-century Museo Cappella Sansevero, which houses thousands of veiled sculptures.
  • Go underground to explore the network of tunnels and passageways built under the city streets.
  • Get outside and see the dormant Solfatara volcano, located a half-hour drive west of Naples.

In the evening, go for a stroll along the Caracciolo e Lungomare di Napoli, a waterfront promenade, then head to the Quartieri Spagnoli, a lively commercial hub, for dinner at a trattoria. On the way, stop at the Toledo Metro station, the Stazione della Metropolitana dell'Arte, to see beautiful mosaic inlays.

Day 9: Private Tour of Pompeii 

Pompeii's perfectly preserved Roman villas

Nature’s fury is our gain; the eruption of Vesuvius in 79 CE meant the preservation of one of the foremost archaeological sites in the world. Today you'll be met by a guide for a two-hour tour of this incredible site just 30 minutes south of Naples. With streets, baths, wonderful frescoes in Patrician villas, not to mention the odd bar and brothel, Pompeii transports you to the glory that was Ancient Rome.

In August, 79 CE, Vesuvius had been rumbling for some days and it is estimated that a large part of the population of 20,000 had been evacuated; those that were left remain suspended in time, as the plaster casts made of the bodies that were found show. Excavation started in the 18th century and continues to this day. The first impression, on entering into the Forum, is just how massive Roman structures were. You will get to walk Roman streets, look into bars, and stroll into villas, complete with frescoes and mosaics. Even ancient graffiti can be seen written on some of the walls, reflecting a forthcoming election. Between the baths, the central heating systems, and the gentle fountains in the courtyards of the villas, you really feel it wouldn’t be too much of a hardship to live there.

Return to Naples in the afternoon and end your penultimate day in Italy with a celebratory meal as the sun sets over the Bay of Naples.

Day 10: Depart Naples

Sunrise over Naples
Sunset over Naples

This morning you'll bid Italy arrivederci and transfer to the airport for your flight home.