Road Trip Italy

Italy Road Trip Itinerary – Milan to Venice

Italy Road Trip

Imagine the excitement of planning an Italian road trip from the bustling streets of New York City. A journey through the amazing countryside, with stunning views and delicious food along the way!

Road tripping around Italy is a great way to explore the many different cities and regions of this beautiful country. It can be an exciting adventure, filled with delicious food, stunning views, and amazing cultural experiences. Whether you’re looking for a romantic getaway or an adventure with friends, there’s something for everyone on an Italian road trip.

If you’re looking for the ultimate Italian road trip adventure, then look no further than Milan to Venice. This route takes you through some of the most beautiful cities and countryside in Italy, stopping off at iconic spots along the way.

Can you fly from New York to Milan?

Yes, you can fly direct from New York to Milan. Several airlines offer direct flights, including American Airlines, British Airways, and Lufthansa.

The flight time is about 8 hours and 20 minutes, depending on the airline and the route. Prices vary depending on the season and when you book your ticket, but expect to pay around $400 to $800 for a round-trip ticket.

If you’re looking for a cheaper option, consider flying with a layover in another city such as London or Paris. This will add some extra travel time but may be more affordable than a direct flight.

Exploring Italy

Exploring Italy by car is a unique way to experience the country’s stunning natural beauty and vibrant culture. From picturesque coastal roads and sweeping mountain passes to winding city streets, there are a variety of routes to choose from when touring Italy. Visitors can drive through the Italian countryside, visit bustling cities like Rome or Florence, or explore quaint villages off the beaten path. Regardless of which route they take, travelers will be sure to discover something new and exciting on their journey.

When exploring Italy by car, visitors should make sure they’re traveling with a reliable vehicle that can handle long-distance drives. Once they’re on the road, it’s important for drivers to familiarize themselves with local traffic laws and customs before starting their adventure.

Planning the Trip

A road trip through Italy is the perfect way to experience all the country has to offer. From its winding coastal roads and hillside towns to its centuries-old cities and magnificent cuisine, there’s something for everyone in this Mediterranean paradise. To make sure your trip is as enjoyable and stress-free as possible, it’s important to properly plan ahead. Here are some tips for making the most of your Italian road trip:

Start by deciding on a route; take into consideration what sights you want to see, how much time you have available, and which type of accommodation works best for you. Once settled on your route, research each destination before setting off – find out what attractions they have to offer, where local restaurants are located and other points of interest that could enhance your stay.

Flying into Milan

We start our itinerary (below) in Milan. Milan is one of the most vibrant cities in Italy, and it’s no wonder why so many tourists are drawn to its charming streets. From historical monuments to world-class museums, there is something for everyone who visits this historic city. For those looking to fly into Milan, there are a variety of options available depending on your budget and preferences.

The Malpensa International Airport is the main international airport serving Milan and it offers flights from all over Europe as well as North America, Asia, and Africa. Travelers can also reach Milan by way of secondary airports such as Linate Airport or Bergamo Orio al Serio Airport which offer more affordable flight options from other parts of Europe. Once you arrive at any of these airports, you can easily get to the center of the city by train or bus with regular services running throughout the day.

Driving in Italy: Rules & Regulations

Planning a road trip through Italy? Before you hit the open roads, it’s important to understand the regulations and rules of driving in the country. Driving laws vary from state to state, but there are some general guidelines that all drivers should follow when touring around Italy.

First and foremost, anyone who wishes to drive in the country must be at least 18 years of age and possess a valid driver’s license from their home country. Additionally, an International Driver’s Permit is also recommended for non-EU citizens. It is illegal to talk on your cell phone while driving in Italy; this includes hands-free devices as well. All vehicles must be equipped with two warning triangles as well as reflective vests for each occupant of the vehicle in case of emergency roadside stops.

Must See Attractions

If you’re dreaming of a road trip to Italy, then look no further! This country is full of incredible sights and attractions that you won’t want to miss. From ancient ruins to breathtaking beaches, here are some of the must-see attractions for your Italian road trip.

Rome, the eternal city, tops our list. Here you can visit iconic landmarks such as the Colosseum, St Peter’s Basilica, and the Trevi Fountain. You can also explore hidden gems like Piazza Navona or take a stroll through bustling Trastevere with its narrow alleyways and cozy restaurants.

For another side of Italy, we will head south to Naples where you’ll find Mount Vesuvius looming above the town. View this active volcano from Pompeii before taking a boat ride over to Capri Island for stunning views of the Mediterranean Sea.

Dining Out Options

As you make your way around the country, you’ll have plenty of dining-out options available. From traditional Italian cuisine to creative dishes with a modern twist, there’s something for everyone’s tastes when it comes to eating in Italy.

Take some time to research eateries before you visit them. The country has a wide range of restaurants from small family-run trattorias offering classic dishes such as spaghetti alla carbonara and pizza Margherita, to chic gourmet establishments serving inventive fare inspired by local ingredients and flavors. If you’re looking for light bites or snacks, then try one of the many bars where you can enjoy coffee, pastries, or small plates of delicious food.

Accommodation Options

When it comes to accommodation options during your Italian road trip, there is something for everyone. Hotels can provide you with comfort and convenience while camping will allow you to get closer to nature. For those looking for an authentic Italian experience, bed and breakfasts or farm stays are a perfect choice; allowing you to immerse yourself in the local culture while indulging in home-cooked food. If all else fails, try Couchsurfing – where locals open up their homes for travelers looking for an affordable stay – or even Airbnb if you’re after more luxury amenities.

Italy Itinerary & Map

The stunning landscapes of Northern Italy offer visitors a wealth of experiences, from exploring its vibrant cities to discovering the region’s stunning lakes and mountains. An unforgettable way to explore this region is with an Italy road trip from Milan to Lake Garda. This route offers picture-perfect scenery, interesting stops along the way, and plenty of opportunities for adventure.

On your journey from Milan to Lake Garda you will be able to experience some of the iconic cities in the area such as Verona, Brescia, and Mantua. Make sure that you take time out to explore these wonderful cities before continuing on your journey. As you continue toward Lake Garda you will pass through some remarkable mountain passes such as Monte Baldo and Passo San Giovanni which are both ideal spots for taking photographs and enjoying the breathtaking views that surround you.


Milan is a vibrant Italian city with a rich cultural history and plenty of attractions to keep any traveler entertained during an Italy road trip. From the iconic Milan Cathedral to the world-class fashion shops, this city has something for everyone. All it takes is a little planning to create an unforgettable experience.

The Duomo di Milano, one of Milan’s most recognizable landmarks and the largest Gothic cathedral in the world, can be seen from miles away. Visitors can explore its rooftop and admire breathtaking views of the cityscape before visiting Piazza Duomo to appreciate more stunning architecture close up. Take some time to learn about Leonardo da Vinci’s famous mural The Last Supper at Santa Maria delle Grazie or visit Galleria Vittorio Emanuele II for some shopping therapy – both are must-sees on any trip to Milan!

The journey from Milan to Portofino is just over 200 km and takes about two and a half hours by car. Along the way, there are some stunning sights that make this drive one of Italy’s most popular road trips. You will pass through rolling hills dotted with olive groves and vineyards and by breathtaking views of Lake Maggiore, Lake Como, and the snow-capped Alps in the distance.


Portofino is the perfect destination for an Italian road trip. Located in the Liguria region of Italy, this quaint fishing village offers stunning views and cultural experiences fit for a romantic getaway. The vibrant harbor is alive with bustling boats and a lively atmosphere, while the surrounding hills are lush with bright green vegetation and lovely homes dotting their slopes. Portofino is more than just a picturesque location – it’s also home to some of the best seafood restaurants in all of Italy. From classic Italian dishes to traditional seafood plates, visitors can enjoy tantalizing meals that will make their taste buds dance with delight.

Portofino Italy

The beauty of Portofino doesn’t stop at its delicious cuisine; there are plenty of attractions to visit as well.

Driving from Portofino to Cinque Terre is one of the most beautiful road trips you can take in Italy. Located on the Italian Riviera, this 170 km journey is full of majestic views and stunning coastal towns. Taking a road trip through this area is sure to be an unforgettable experience that will stay with you for years to come.

As you drive from Portofino to Cinque Terre, you’ll be able to enjoy breathtaking views of the Mediterranean Sea and explore charming villages like Santa Margherita Ligure, Rapallo and Chiavari. Nature lovers will particularly appreciate the green hills dotted with picturesque vineyards and terraces which provide some of the most spectacular scenery in Italy.

Cinque Terre

The Cinque Terre area of Italy is an ideal location for a road trip. Located along the northwest coast of Italy, this rugged region offers stunning views and plenty of activities to keep you busy. Featuring five picturesque fishing villages, colorful homes built into the side of cliffs, and an abundance of local seafood dishes, it’s easy to see why Cinque Terre is a popular destination for travelers looking to explore Italy by car.

Cinque Terre

Starting your journey in La Spezia, you’ll be able to drive along the spectacular coastline and make stops at each village. Spend time strolling through Vernazza’s winding cobblestone streets or take a dip in Manarola’s crystal-clear waters before heading further up the coast.

The drive from Cinque Terre to Pisa takes approximately two hours and is best completed during daylight hours as it passes through many small mountain roads with frequent sharp turns. Along the way, take time to view the sights such as Castello di Bardi, an ancient castle nestled in a hillside village, or enjoy lunch at one of many restaurants located on picturesque lake shores.


Pisa is a city located in Tuscany, Italy. It is most well-known for its iconic leaning tower, the symbol of the city, and one of the world’s most remarkable monuments.

The Leaning Tower of Pisa stands 56 meters tall and has been tilting since 1173 after construction began on the bell tower more than 800 years ago! Seeing this grand structure with your own eyes will take your breath away and make for an unforgettable experience. The surrounding area known as the ‘Field of Miracles’ also houses other breathtaking structures such as Pisa Cathedral, Baptistery, Monumental Cemetery, and Museum that any visitor should check out to get a full appreciation of Italian architecture from centuries past.


The drive from Pisa to San Gimignano takes just over an hour so there’s plenty of time to explore en route. On your journey from Pisa to San Gimignano, make sure you take a few detours! Stop by picturesque vineyards or explore one of the traditional villages nearby for a real local experience. There are also plenty of restaurants along the way where you can try some authentic Italian cuisine like fresh pasta dishes and wood-fired pizzas.

San Gimignano

San Gimignano is a picturesque Italian hilltop town located in the province of Siena, Tuscany. It’s one of the most popular stops on an Italy road trip and for good reason – its well-preserved historic center has been declared a UNESCO World Heritage Site.

San Gimignano

The picturesque cityscape of San Gimignano is dominated by 14 medieval towers that were built during the 12th century as symbols of wealth and power. The city also boasts beautiful narrow cobblestone streets lined with art galleries, boutiques, cafes, and restaurants serving up traditional Tuscan fare. Visitors who make it to the top of Torre Grossa (the tallest tower) will be rewarded with breathtaking views over San Gimignano’s unique skyline, rolling hills, and neighboring vineyards – a truly unforgettable sight!

San Gimignano is sure to be one of the highlights of your Italian road trip. From there, you’ll make your way south along winding roads until you reach Siena – another beautiful Tuscan town that’s home to amazing architecture and delicious food. Driving from San Gimignano to Siena is a journey full of stunning landscapes and endless discoveries. This winding route through rural Italy offers spectacular views of vineyards, olive groves, and ancient hill towns along the way. Plus, it takes just over an hour to complete!


Siena, Italy is a stunning destination for those looking to explore the country on a road trip. Located in the center of Tuscany, this walled city is known for its Medieval and Gothic architecture, cobblestone streets, and unique art. It’s not hard to see why this location has been so popular over the years – from its picturesque atmosphere to its old-world charm.


For centuries Siena was an independent republic that flourished due to banking and agriculture. Today visitors can get a glimpse at what life used to be like by taking in all of the sights throughout town. The Piazza del Campo, with its iconic red brick fan-patterned square, and the Torre del Mangia tower which towers over it are both must-sees when visiting Siena.

The drive from Siena to Montepulciano is an exciting and rewarding journey that shouldn’t be missed. This drive is one of the most beautiful routes in Tuscany, as it winds through ancient villages, rolling hillsides, and iconic vineyards. Along the way, travelers can take in some of the most breathtaking views in Italy.

The drive itself takes about 45 minutes and follows a picturesque route through Val d’Orcia, a UNESCO World Heritage Site known for its rural beauty. As you make your way along the winding roads, you’ll have ample opportunity to spot local wildlife such as foxes or wild boars, and admire gorgeous vistas that reach all the way to southern Tuscany’s highest peaks.


This picturesque town is known for its red wines and stunning views. With its rolling hills and vineyards, Montepulciano offers travelers a chance to take in the beauty of rural Italy while also exploring some of the country’s most renowned wineries.

A visit to Montepulciano will start with its old town, which is filled with narrow cobblestone streets lined with Renaissance-era buildings and churches. A walk along these streets will give visitors an opportunity to explore local shops that offer traditional Tuscan products such as pottery, leather goods, and jewelry.


Driving from Montepulciano to Rome is a great way to experience the beauty of Italy on a road trip. This route passes through rolling hills, olive groves, and vineyards that make for some spectacular scenery. The drive is about 120 miles long and can take up to three or four hours with traffic.

The best time to start your journey is early in the morning when the roads are less congested, so you can enjoy the stunning views along the way in peace. Before embarking on this journey, it’s important to ensure your vehicle is up-to-date with all necessary documents and safety requirements as needed by Italian law.


For those seeking a classic Italian experience, a road trip to Rome is a perfect choice. With its diverse history, culture, and scenery, this city has something for everyone. From the ancient ruins of the Roman Forum and Colosseum to exquisite Renaissance-era art masterpieces in the Vatican Museums, Rome is an unforgettable destination.


Rome’s streets are filled with centuries-old buildings with unique facades and cobblestone passageways inviting exploration. As you stroll through these romantic thoroughfares, take time to savor some of Italy’s best cuisine which can be found in any number of restaurant hotspots throughout the city. Make sure to try out local specialties such as Pasta Carbonara or Tiramisù for dessert!

Traveling from Rome to Spoleto is a captivating journey filled with stunning views of Italy’s countryside and historic towns. This drive will take you approximately two and a half hours through some of the most picturesque landscapes in Europe.

You’ll pass by rolling hills and ancient monasteries as you make your way north to Spoleto. Along the route, there are plenty of opportunities to pull over and explore nearby attractions such as Tivoli or Civita di Bagnoregio, giving travelers plenty of time to admire the beauty of this route firsthand. Once arriving at Spoleto, visitors can enjoy its charming atmosphere while admiring its historical monuments, churches, and archaeological sites.


Spoleto is a small town located in the Italian Province of Perugia. It is the perfect destination for your Italian road trip. Nestled at the foot of Monte Subasio, Spoleto’s cobbled streets, stunning architecture and vibrant culture provide an unforgettable experience.


The historic center of Spoleto boasts some excellent attractions; tourists can explore Ponte delle Torri – a bridge built by architect Antonio da Sangallo in 1476 – or head to Rocca Albornoziana, a 14th-century fortress with stunning views over the city’s skyline. Or take a stroll through one of the many winding alleyways to discover hidden piazzas and churches scattered throughout Spoleto’s charming old town.

Spoleto to Assisi is a picturesque drive through the hills of Umbria, Italy. This beautiful and historic route has something for everyone – from stunning views of rolling hills to quaint medieval towns along the way. Located in central Italy, this 90-kilometer journey is just over an hour’s drive without stops.

The route passed through small villages and vineyards with spectacular views of green valleys dotted with olive groves and wildflowers as far as the eye can see.


Assisi is an essential stop. The ancient hill town in Umbria is home to some of the most beautiful medieval architecture and art in all of Europe. Founded by Saint Francis around 1205, Assisi has declared a UNESCO World Heritage Site in 2000.


A visit to Assisi should begin with exploring its cobblestone streets, lined with picturesque buildings that are hundreds of years old. Visit the Cathedral of San Rufino for stunning gothic architecture or take a walk up Mount Subasio for breathtaking views of the countryside below. There are plenty of historic churches and basilicas scattered throughout Assisi as well – including Basilica di San Francesco which houses some incredible frescoes painted by Giotto and Cimabue – so make sure to explore!

Driving from Assisi to Florence is approximately a two-hour drive that takes you along the stunningly beautiful countryside of Umbria and Tuscany, with breathtaking views of vineyards, rolling hills, medieval towns, and villages. It’s an exciting journey that will leave travelers with lifelong memories.

The road between Assisi and Florence starts at the historic tourist destination of Assisi, where travelers can explore its many churches and monasteries before hitting the road. From there they will wind through small villages like Spello and Montefalco before reaching Perugia where they can enjoy lunch or take some time to explore the old town center. Then it’s on to Arezzo where visitors can learn more about this ancient walled city before beginning their final stretch towards Florence.


Florence, Italy is an iconic destination for roadtrippers across the globe. The city’s stunning architecture, cobbled stone streets, and enchanting Renaissance-era vibe make it a must-see stop on any Italy road trip. As the birthplace of the Renaissance, Florence is home to some of the world’s most renowned works of art. From Michelangelo’s iconic David to Botticelli’s “The Birth of Venus,” visitors can explore centuries worth of culture at some of Florence’s top attractions such as the Uffizi Gallery and Pitti Palace.


Beyond these iconic masterpieces, travelers will find a variety of activities in Florence that embody its rich cultural heritage. Stroll along Ponte Vecchio for spectacular views and shopping or take a guided tour through Boboli Gardens for its lush green scenery.

The route (less than 200 miles) from Florence to Bologna provides travelers with the opportunity to admire stunning views of Tuscany’s rolling hills, Italian countryside, and unique cities along the way. The journey takes around three hours at a leisurely pace, offering plenty of time for sightseeing and stops for lunch or coffee at charming local cafés.

Driving from Florence to Bologna is an easy experience with good roads and clear signage leading the way. Motorists should plan ahead if they want to avoid busy highways during peak times; there are also several scenic backroads that wind through picturesque villages if travelers would prefer a leisurely drive through rural Italy instead.


You can’t miss the city of Bologna. Located between the Po river and the Apennine mountains in northern Italy, Bologna is known for its rich culture, vibrant nightlife, and delicious food. The city has some of Italy’s most beautiful architecture with cobblestone streets and arcades that will take your breath away.


When visiting Bologna, make sure to explore one of Europe’s oldest universities, which dates back to 1088! You can also visit museums such as the National Gallery of Art or enjoy some shopping at Via Ugo Bassi. And when it comes to dining out in Bologna you are spoilt for choice; from traditional Italian cuisine to modern gastronomy – there is something for everyone in this historic city.

Traveling from Bologna to Venice is a great way to explore the beautiful Italian countryside. Driving along the A13 motorway, visitors will have spectacular views of the rolling hills and vineyards of northern Italy for much of their journey. The entire drive takes about two and a half hours, making it easy to fit into any vacation itinerary.

The route follows an ancient Roman road from Bologna to Padua before heading toward Venice. Along the way, travelers should take in sights such as Medieval castles and rustic villages that dot the landscape. Drivers can also make stops at Verona, home of two UNESCO World Heritage Sites, and Vicenza, known for its Palladian architecture.

Once travelers arrive in Venice they are free to explore all this incredible city has to offer.


A trip to Italy is incomplete without a visit to Venice, the romantic city of canals and bridges. This unique Italian city offers plenty of sights and activities for the perfect road trip! Take a romantic gondola ride down one of the many canals, explore St. Mark’s Square, or discover hidden gems off the beaten path.

From breathtaking art galleries to buzzing cafes, there is something for everyone in Venice. Shop for handmade souvenirs at one of its colorful markets or take in some local culture by attending an opera or theatrical performance. Afterward, enjoy a classic Italian dinner at one of its award-winning restaurants and cap off your day with some late-night drinks along the waterfront promenade.

Making the journey from Venice to Lake Garda is an exciting way to discover the incredible sites and sounds of northern Italy. From the historical city center of Venice to the picture-perfect lake town of Malcesine located on Lake Garda, travelers can enjoy a scenic route filled with breathtaking views.

The drive from Venice to Lake Garda takes approximately two hours, depending on traffic and weather conditions. The A4 autostrada is recommended for this journey as it passes through some truly stunning scenery along its path.

Lake Garda

Spanning the rolling hills of Northern Italy, Lake Garda is one of the most beautiful and sought-after destinations for a road trip. With its long stretches of shoreline, quaint villages, and stunning scenery, it’s easy to see why taking a road trip around this picturesque lake is an experience not to be missed.

Lake Garda

The warm Mediterranean climate makes Lake Garda an ideal destination all year round; whether you are seeking sun-soaked beaches in summer or snow-capped mountains in winter, there is something here that will take your breath away. Its location in the heart of Italy offers visitors easy access to a host of attractions including historical sites, cultural activities, and delicious cuisine – perfect for any Italy road trip!

Final Word

Italy is a truly spectacular country with so much history and culture to explore. A road trip from Milan to Venice offers the perfect opportunity to experience it all – from the bustling city of Milan, to the romantic canals of Venice. From historical cities like Padua and Bologna, to the breathtaking views of Lake Garda, you can tailor your itinerary for a unique Italian adventure. So what are you waiting for? Pack your bags and hit the open road for the perfect Italian escape!

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