The Ultimate Bucket List Italy Road Trip

Planning a trip to Italy? This gorgeous country is perfect for a road trip. Compact and with all the best bits in the middle, you’ll be blown away by the landscapes, architecture and food in this sublime country. Take a bucket list road trip to Italy and see it for yourself!

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Italian Road Trip Basics

Lots of people will tell you that renting a car in Italy is madness, that driving through Italy is dangerous and the roads are dreadful.  It is true that some routes can be challenging to drive in Italy, and in big cities, Italian drivers see it as a badge of honour not to give way. Isn’t that the same in most big cities nowadays though?

Don’t let your fears about driving in this beautiful country put you off taking Italian road trips. Take your time and follow our driving in Italy tips, so that you are prepared for the differences in driving styles and roads from back home. With our Italian road trip itineraries, you’ll find lots of time to relax away from the car and enjoy the stunning surroundings. 

Italy Itinerary & Map

Italy road trip map

DISTANCE | 1670km

DURATION | 2 – 4 weeks

DRIVE TIME | 23 hours

WHEN TO GO | spring & autumn

PLACES VISITED | 14

1. Milan

2. Portofino

3. Cinque Terre

4. Pisa

5. San Gimignano

6. Siena

7. Montepulciano

8. Rome

9. Spoleto

10. Assisi

11. Florence

12. Bologna

13. Venice

14. Lake Garda

Italy Road Trip
1 Week

Fly into Pisa instead, skip San Gimignano, Spoleto and Montepuciano. Head home from Pisa once you’ve seen Florence.  

Italy Road Trip
2 Weeks

Skip Pisa, Spoleto, Venice and Lake Garda…tough choices, but come back for a second trip.

Italy Road Trip
3 Weeks

You have enough time to complete the itinerary above. You will have one day in most places, 36 hours in Rome and Florence.

Italy Road Trip
4 Weeks

Revel in the time you have and spend longer in Rome and Florence. Maybe add Arezzo and Verona to your itinerary or check out the Amalfi coast.

Milan

An Italy road trip starting in Milan is so easy to plan. Milan is the perfect airport to fly in and out of for this northern Italy road trip itinerary. With direct international flights from all the world’s continents, it’s accessible, has great car hire options and it’s a pretty kick-a** city to visit!

If you didn’t already know, Milan is a global capital of design and fashion and delivers on sleek and simple Italian style at every turn. Milan’s creativity and design flair is not a recent phenomenon though. The city has been at the forefront of the arts throughout history and this can be seen in the spectacular Gothic Duomo di Milano cathedral and the UNESCO World Heritage Site of Santa Maria delle Grazie, home to Leonardo da Vinci’s ‘The Last Supper’. 

If you fancy a bit of shopping in this city of designer boutiques and couture labels, then visit the spectacular Galleria Vittorio Emanuele II, Italy’s oldest shopping mall, and unlike any other shopping mall you’ve visited before!

Stay at one of the airport hotels and get the train or bus directly into the centre of Milan, it will take around 30 minutes and cost €10-15. If you’re splashing out, get a cab for around €100. If you decide to spend a night in Milan, save money and delay your car rental pick-up until the following day, then hit the road for the best road trip route in Italy!

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Portofino

Head south to Portofino, a gentrified fishing village on the Italian Riviera coastline of the Ligurian Sea. Pastel painted houses line the picturesque harbour, mixing effortlessly with stylish and bijou stores, seafood restaurants and cool bars. The charming Piazzetta, a small cobbled square, overlooks the harbour which is lined with super-yachts in the summer and more traditional craft in spring and autumn. 

Spend a day soaking up the atmosphere and people watching. Grab a slice of delicious focaccia con il formaggio (focaccia with cheese) from nearby Recco and meander along the winding backstreets, whilst indulging in a bit of window shopping.  

Head to San Fruttuoso, a stretch of Mediterranean coast which you can only get to by boat or on foot. Enjoy lunch at a cantina on one of the beautiful terraces, where we ate one of the best tomato salads we have ever experienced. 

Spend some time on the warm turquoise water in a kayak or on a paddle board; make sure to take a snorkel and mask with you too, the water here is crystal clear.

Head back to dry land and enjoy dinner at one of the many seafood restaurants in the harbour, for a perfect end to your first full day in Italy.

Stay at the Hotel Piccolo Portofino for it’s large and airy rooms, tiny private beach and fantastic views. Situated in a modernised convent, this hotel sits on the lush slopes above Portofino – it takes around ten minutes to walk along a quiet and pedestrianised path to the harbour which is great for working up an appetite, or walking off dinner! 

Cinque Terre

You could easily spend a week or more in this wonderful national park, especially if you enjoy hiking and water sports. Cinque Terre is a group of five historic seaside villages on the rugged Italian Riviera coastline and a real bucket list destination. Pretty and brightly coloured houses cling to dramatic terraced streets, harbours are filled with traditional fishing boats bobbing on clear azure waters and trattorias serve up everything with homemade pesto (basil, olive oil, parmesan cheese and pine nuts), the traditional sauce of the region.

The Sentiero Azzurro cliffside hiking trail links the five villages of Monterosso, Vernazza, Corniglia, Riomaggiore and Manarola. The trail offers incredible sea views and easy walking. If you’re more of a water baby, see the Cinque Terre villages from a kayak, or take a boat trip and avoid the inevitable crowds in the towns.

Cinque Terre, all the best Italian road trips stop here
Riomaggiore

Like driving the Amalfi Coast, going to Cinque Terre in a car can be challenging and you should read this Cinque Terre guide before you decide how to visit. If you do decide to stay or park in Cinque Terre, head for delightful Monterosso al Mare, the largest of the Cinque Terre towns, and start your amble along the hiking route from there. Otherwise stay in La Spezia and get the early train to make the most of your day.

Stay at the Hotel Porto Roca for it’s beachside location, panoramic sea views and swimming pool. The hotel is decorated in a slightly dated Italian style, but the service is excellent and they provide complimentary chairs and shades at the nearby beach as well as free transfers from the nearby train station. 

Pisa

It’s pretty much all about the leaning tower here, as much of the town was sadly lost during WW2 bombing. Head for the Campo dei Miracoli (Field of Miracles) where you’ll find the iconic tower, fine Romanesque duomo, Gothic baptistry and camposanto (cemetery). This beautiful quartet of creamy coloured historic buildings sit on an open and grassy area, enabling the infamous instagram shots of people seeming to hold up the infamous tower.  

If you’re on a deadline, the best way to enjoy Pisa is to take a two hour tour of these important monuments, as you pass through on your way to the next stop.

Stay at the small and stylish Palazzo Cini in central Pisa. Within easy walking distance of the Field of Miracles and offering parking, this welcoming hotel, with a gorgeous private garden, is the perfect Pisa stop.

San Gimignano

As you approach this most archetypal of Tuscan hill villages, you’ll see it’s thirteen towers dominating the skyline. Historically, the town was on the main pilgrim route from Northern Europe to Rome and the towers were built by merchants to show the world their power and wealth.   

San Gimignano is now beautifully preserved and perfect for an afternoon meandering the atmospheric narrow cobbled streets and piazzas. Make sure to visit the ancient Torre Grossa, the only one of the thirteen towers open to visitors. Other must sees are the stunning frescos in the 11th century Collegiate and the ornamental Rococo interior of Sant’ Agostino church. Otherwise, grab a gelato or a coffee and stroll to your hearts content

San Gimignano, one of the best places to visit on a road trip to Italy
San Gimignano

Stay at the traditionally charming Relais Santa Chiara Hotel, within 500m of the old town walls and a gentle stroll into the busting squares of San Gimignano.  With beautiful gardens and an inviting pool, this is a wonderful spot to take a break for a few days if you have time.

Siena

Siena is gloriously Tuscan, it’s warm colours beckoning you into the medieval streets and towards the jewel in Siena’s crown, the famous Piazza del Campo. The prettiest of Tuscany’s must see towns is not only home to one of Europe’s greatest medieval squares, but a wealth of stunning religious and civic buildings and a busy shopping area packed with interesting galleries and boutiques.

The Piazza del Campo is an extraodinary site as you enter from Via di Citta and fully appreciate the symmetry, layout and beauty of the square. Lined with fine buildings which will grab your attention, don’t miss the tiny Fonte Gaia on the northern edge of the piazza, whose water is still supplied by a 500 year old viaduct.   

Take a walking tour of Siena and the duomo to fully appreciate the city’s turbulent history and breathtaking architecture. Stop for lunch at one of the many lively restaurants lining the streets around the main square and sample delicious Ribollita, a traditional Tuscan soup made with vegetables and bread, before heading off on one of the best drives in Italy.

Siena a must see on Italy road trips
Siena

Driving in Tuscany is one of the greatest pleasures of this road trip. As you leave Siena for Montepulcianao, you’ll be motoring through some of Italy’s most iconic and stunning scenery. Head south, setting your sat nav for the Val d’Orcia, and enjoy one of Europe’s best driving routes. This journey will take you through vineyards and olive groves, and you’ll pass row upon row of majestic cypress trees lining the roads and on the skyline. If you pick up the SP146 between San Quirico d’Orcia and Montepulciano, you might even spot the famous house from the film ‘Gladiator’, some of which was shot in Tuscany.

Val d'Orcia best of Italy scenic drives
Val d'Orcia

Montepulciano

Famous for the classic, rustic wine of the same name, this is gorgeous medieval town is nestled into the chalky hills at the meeting point of the Val d’Orcia and the Vall di Chiana. Surrounded by the classic Tuscan landscape of rolling green hills and golden fields dotted with cypress trees, this is your picture perfect Tuscany road trip destination.

The town itself is a masterpiece of cobbled streets, charming piazzas, restaurants and gift shops which can easily draw you in for a deliciously pleasant afternoon and evening.  Enjoy a meal of wild boar ragu, followed by local cheese and honey washed down with the famous Vino Nobile di Montepulciano. The town is also one of the best spots in this itinerary for a wine tasting tour of a local vineyard, to understand the history and process of making wine in Italy.

You cannot park within the town walls and need a permit to park in one of the numbered car parks on the outskirts, which your hotel will provide for you. The car parks are around a ten to fifteen minute walk from the centre of the town, so maybe pack a small bag for an overnight stay. 

Stay at the wonderfully unique Palazzo Carletti. This restored aristocratic B&B is right in the heart of town and enjoys incredible views across the surrounding countryside.  With just five rooms, this intimate and charming palazzo is a B&B come hotel, with all the touches you would expect from the latter.  

Italy Road Trip Ideas

Rome

The centre of a vast empire and capital of the Christian world for centuries, Rome is full of the works of the artists and architects who gathered here to work for the Popes and their wealthy families. This magnificent legacy has assured the eternal city’s position as one of the most important historical places in the world.  

If you have four weeks or longer, one of the best road trips from Rome is to head south for around three hours to the Amalfi Coast. This stunning stretch of gravity defying road from Sorrento to Salerno passes by the beautiful beaches of Positano and the romantic village of Ravello, and is considered the best Italian coast road trip of them all.

Spoleto

Driving from Rome to Florence you’ll find Spoleto, often over-looked in favour of it’s famous neighbours but a true hidden gem. Nestled in a beautiful wooded setting in Umbria, the town is famous for the Festival dei Due Mondi (festival of the two worlds) held in June and July annually. Outside of this time, tourists are welcomed, but not thick on the ground like they are in next-door Assisi. Spoleto’s independent nature has allowed it to thrive and progress as a town in its own right, rather than a tourist hot spot.

Come to Spoleto to enjoy a slow day, sipping coffee in the square, taking the travelator (an experience in itself) up to the mighty fortress of La Rocca Albornoz, which dominates the skyline, and wandering around the many beautiful churches and religious buildings in the town. 

Stay at the highly rated Palazzo Sant’Angelo B&B, with its beautifully simple decor and fabulous views. With a great central position, this lovingly renovated historic building is a masterclass in hospitality and comfort…and the breakfast is amazing too!

Spoleto

Assisi

The birth and final resting place of St Francis of Assisi, this beautiful medieval hill town, with its geranium filled streets, charming piazzas and panoramic views is a must see on your Italian road trip itinerary.  

Wreathed in history and religion, the magnificent Basilica di San Francesco draws pilgrims and tourists from across the globe. Clinging to the side of a craggy outcrop and visible for miles, the Basilica dominates the town and surrounding landscape.  Spend the day wandering between here and Assisi’s main square, Piazza del Comune, where the Roman columns of the Templo di Minerva still stand. There are many other religious buildings of note, a walking tour with a private guide will help you understand the importance and history of each. 

Stay at the superb Nunn Assisi, with its modern spa in the roman ruins excavated underneath the building. This restored hotel has very stylish rooms and the most beautiful gardens full of graceful lavender and rosemary, with the odd olive tree dotted around. Breakfast here is a delight.

Assisi a must see on your road trip Italy 2 weeks
Assisi

Florence

Florence is a vast and graceful monument to the Renaissance, the period of cultural and artistic rebirth following the Middle Ages. Many famous artists such as Michelangelo and Botticelli contributed to Florence’s heritage, making it one of the artistic capitals of the world. 

Historic Florence is compact and walkable and could be seen in a day, if you’re ruthless in your selections. Better to spend two days here and visit the must sees of the exceptional Duomo, stunning Palazzo Vecchio, the sublime Uffizi Galleries and the ancient church of Santa Croce. Across the river Arno, via the Ponte Vecchio, lies the vast and imposing Pitti Palace and the Santa Spirito church. Book everything in advance, whether that’s tickets, tours or guides; this city never sheds itself of tourists, all clamouring to see the same things as you!  

Stay at the Hotel Spadai, a hop and a skip from the Duomo. You will have to navigate Florence’s centre to get to it’s private parking garage, so choose an out of town hotel if the thought if this terrifies you. Stay here and you’ll have a fabulous view of the Duomo dome, a supremely comfortable bed and a lovely welcome.  They like to upgrade here if they possibly can, you may get lucky out of season.

Bologna

The foodie capital of Emilia-Romanga, and possibly the whole of Italy, Bologna will suprise and delight you. Follow our self-guided foodie walking tour of Bologna to sample the best food and architecture the city has to offer. 

If you have time, pop across to Modena to sample the famous Balsamic vinegar made there, and then Parma for the ham of the same name.

Venice

Ah, Venice. This unique city has survived against all the odds; built on on a series of mud banks and in the tidal waters of the Adriatic, Venice regularly floods. Despite this, little of the essential fabric and infrastructure of Venice has changed in 200 years, and more than 20 million visitors a year fall in love with the beguiling city of water.

Trying to see Venice in a day will not do it justice, and leave you feeling frustrated. If that’s all you have, either come back another time or take a private full day trip so you can be whisked around and see all the best bits, without getting lost.

Whenever you visit and whether you chose to see the religious and historic buildings, the famous islands of Murano, Burano and Torcello or take a gondola along the Grand Canal, Venice will be crowded. Organise your Venice itinerary carefully so that you can fit everything in; two days will be just about enough if you get up early each morning!

Stay at the slightly off the beaten track Hotel Moresco. This friendly and classically decorated Venetian hotel is perfectly located for parking and rail links, with water taxis going from the front door.  It will take 20 minutes of walking, through fabulously picturesque streets, to get to the main sites, which helps open your eyes to the delightful and less visited parts of Venice. Park at Garage San Marco Venezia, (book well in advance) a five minute walk from the hotel. There is no free parking in or around Venice, expect to pay at least €25 per 24 hour period.

Venice

Lake Garda

Your final stop before heading back to Milan, to drop off your hire car.  Lake Garda, the most well known and largest of the Italian lakes, borders three regions; Trentino, Lombardy and the Veneto. The further north along the lake you go, the more dramatic the landscapes become, as you head towards the snowcapped Alps. 

There are many places to stay on Lake Garda, all offering opportunities for water sports, hiking and relaxing at the end of your epic road trip of Italy.  Our pick is Bardolino on the east shore, a lively town with easy access to the lake and lots going on, as well as spectacular sunsets over Lake Garda to end your day.

Stay at the stunning and highly recommended 16th century Locanda San Vigilio just north of Bardolino, on a gorgeous peninsula. With a lakefront setting, private harbour, beautifully landscaped gardens and its own beach, this is a perfect hotel to end to your Italian road trip in style.

One of the best places to stay on a road trip Italy
Locanda San Vigilio, Lake Garda
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A Bucket List Italian Road Trip

This road trip itinerary in Italy takes you to all the must see places and some hidden gems too. A road trip in Italy for 1 month or 1 week! itinerary.#italyroadtrip #roadtripitaly #visititaly #italyroadtripitinerary #italytraveltipss #italianroadtrip

A Flexible Road Trip Itinerary Italy

A four, three or two week Italy road trip guide with interactive map, hotel and activity suggestions #italyroadtrip #roadtripitaly #visititaly #italyroadtripitinerary #italytraveltipss #italianroadtrip

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