Bucket List-Worthy Italy Road Trips

07 August 2023

Italy Road Trip

Just when you think you know a country, being behind the wheel opens new, limitless possibilities. A road trip in Italy allows you to go at your own pace, steering the trip wherever your heart takes you. It becomes about the journey, where unique experiences and hidden gems unwind from the horizon and your relationship with Italy goes from holiday romance to great love.

With fantastic motorways and well-connected cities, Italy is a perfect location for a road trip. But if the idea of navigating the Autostrada is not for you, then jump into the back seat and let Scott Dunn’s drivers do it for you.

How Many Days Do You Need for a Road Trip in Italy?

Allow yourself to meander slowly between the stunning scenery and take at least a week for your road trip in Italy. It is possible to do shorter journeys between two places in just five days but to sink into the true spirit of a leisurely holiday, put aside a week or two. All our itineraries are flexible and tailor-made to suit your time, but it’s also important to be realistic, you can’t see all of Italy in 10 days, for example.

How to Plan Your Italy Road Trip

Planning a road trip can seem like more work than a fly-and-flop holiday. But that is where our travel experts come in. Before you speak to them, though, you might like to start thinking about how your ideal road trip in Italy could look, starting with where you want to go.

Italy has more than its fair share of scenic journeys, from the statuesque Dolomites to the rolling hills of Tuscany and the glistening Italian lakes. Think about which destinations appeal to your interests, whether it's about being outdoors and active, getting lost in art, history and architecture, or following the Michelin star restaurants.

Next, think about how long you and your travelling companions (particularly if they are children) are happy to sit in a car for. Some of our itineraries have shorter distances between stops, while for others you could be driving for several hours. How long you have for your road trip is also key in deciding how many nights you'd like to spend at each destination.

What type of car you would like to travel in is another factor to consider. You want to be comfortable driving over different terrains while having enough space for everyone and their luggage. Equally though, if it is a vintage convertible that you dream of, let us know, and we can organise that too.

Assess the season that you are travelling in for weather conditions and public holidays. Popular roads and sights get very crowded in the summer months and when locals are likely to be on the move too. If you aren’t tied to the school holidays, make the most of the beautiful out-of-season periods in spring and autumn.

What style of accommodation you are looking for will also dictate your itinerary. If you prefer five-star Grand Dame hotels, you will need to make your stops in the bigger cities and more popular tourist sites. For more boutique and low-key options, you will want to stop somewhere rural or off-the-beaten-track.

Lastly, let your travel expert know about any special interests or hobbies you have so they can match them up to the cultural and historical highlights of each destination. There might be festivals or events happening around the time of your trip, which will add to the rich experience of driving through Italy.

The Best Italy Road Trips

From spectacular drives past lakes and up mountains to shorter experiences with just a hint of a road trip about them, these are the routes in Italy worth exploring on wheels.

Venice and the Lakes

Length: 1-2 weeks

Why we love it: Combine a stop in one of the world's most beautiful cities with charming lakeside towns oozing with style and spectacular scenery. Lovely for couples.

Fly into Venice for a few nights, before returning to the airport to collect your car - you don't want a car in Venice, as the streets are pedestrianised. Head towards Lake Garda, stopping at Monte Baldo near Malcesine for a fabulous hike with 360-degree views and a rewarding lunch. Then carry on to Riva del Garda for a few days of water sports and wandering in pretty towns. If you have more than a week for your road trip in Italy, you might like to go on to Lake Como. Explore the charming historic centre and nearby Villa Olmo and take the swooping road up to Bellagio for its pretty gardens. There is so much to do around Lake Como from outdoor activities like cycling, hiking and boat rides, to stunning Gothic and Renaissance architecture. From here you could head on to Milan or fly home from Venice or Verona.

Where to stay: In Venice, stay at Palazzo Experimental for a grown-up contemporary style or the Belmond Hotel Cipriani to make the most of its outdoor pool in the warmer months. Once in Lake Garda, families will love the one-, two- and three-bedroom suites and dedicated water sports centre at Du Lac et Du Parc Grand Resort, while couples should head to Lido Palace for a more boutique experience. In Lake Como, stay closer to Bellagio and relax in the eclectic Mandarin Oriental Lago Di Como, or head just across the lake for the iconic Grand Hotel Tremezzo.

Verona to the Dolomites

Length: 10 days – 2 weeks

Why we love it: This Italian road trip has a little bit of everything: city, lake, and mountains. It’s better suited to families with older children or teens and active adults.

Start in Verona, a charming city with fairy-tale architecture, and spend a few days exploring and visiting the spectacular open-air opera if you are driving through Italy in the summer. Then, head out of the city towards Lake Garda, stopping at Vecchia Malcesine – Malcesine’s Michelin-star restaurant – for lunch. Make your base near Riva del Garda on the north of the lake and get your fix of discovering beautiful villages, water sports on the lake and amazing food. Continuing north, make your way to the Dolomites, aiming for San Cassiano, with a stop in the UNESCO World Heritage site Alpe de Suisi, the largest high-altitude alpine meadow in Europe.

Where to stay: Opt for Due Torri in Verona for rooftop views and classic Italian interiors or Du Lac et Du Parc Grand Resort for family-friendly accommodation. In Lake Garda, Lido Palace is ideal for a mature atmosphere, Alpina Dolomites is a must in the Alpe de Suisi, and in San Cassiano, Hotel Fanes and Ciasa Solares will both give you a taste of traditional Tyrolean life.

Florence to Siena

Length: 1 week - 10 days

Why we love it: Roads lined with tall, narrow cypress trees, ochre fields, and rustic farmhouses, this is the perfect road trip for families wanting to switch off.

Fly into Pisa and drive to the outskirts of Florence in the countryside. Spend a few days being shuttled between the romantic art and architecture in the city and the peace and quiet of the hotel grounds. Drive into the Chianti Region for wine tasting, bike rides, cooking classes and relaxation, before making your way back to Pisa, via Siena. If you have more time, you could always go on south to Rome or cruise across to Perugia, via Montepulciano.

Where to stay: Il Salviatino and Villa Cora are both just outside Florence with easy access to the city and beautiful surroundings, plus outdoor swimming pools. Stay at the exquisite COMO Castello del Nero or Castel Monastero in Chianti, while families should stop at Borgo Pignano on the way to Siena.

Val d’Orcia & Umbria 

Length: 1 week – 10 days

Why we love it: This road trip in Italy is perfect for couples or groups of friends looking for a peaceful, laid-back holiday, with wine-tasting pit stops along the way.

The Val d’Orcia route is one of the most famous in Tuscany, leading you around the region’s iconic countryside dotted with yellow fields and Medieval villages. Start in Florence or Perugia and follow the gently winding roads towards Val d’Orcia, stopping in charming towns like Pienza or Montalcino. Spend a few days or a week exploring the area, soaking in the views, sampling the wine, and then make your way towards the Tuscany/Umbria border, stopping for lunch at Citta’ della Pieve.

Where to stay:You are spoilt for choice with accommodation in Val d’Orcia, some of our favourites are the Rosewood Castiglion del Bosco, Borgo Pignano, and Villa San Luigi. Then, stay at Castello di Reschio near Umbria.

The Amalfi Coast

Length: 1 day

Why we love it: More of a scenic drive than a road trip, this is one for the honeymooners among you.

The journey from Positano to Vietri Sul Mare is one of the more beautiful scenic routes in Italy. It only takes a couple of hours but in this serene setting, it will feel like time has slowed down as you take in all that is so special about this part of Italy. You will cruise past colourful houses, rows of lemon trees, bays lined with cypress trees, and pockets of the beach just calling out for you to swim in. This is the incomparable Amalfi landscape where nature reigns supreme.

Where to stay: Base yourself at Casa Angelina in Praiano or Palazzo Avino in Ravello, both beautiful places from which to explore.

Sicily – Catania to Palermo

Length: 10 days – 2 weeks

Why we love it: Sicily has it all, a rich, complex history that left incredible art and architecture, wild and beautiful scenery, beaches you’ll want to spend all day on, and palazzos good enough for White Lotus. An Italian road trip in Sicily works for everyone – families can make the journey shorter while grown-up travellers can spend longer traversing the island.

Start in Catania but make your way straight out of the city as it’s not easy to navigate with cars. From there head along the coast towards Taormina for Baroque architecture and bougainvillaea-framed views of Mount Etna. Drive inland to get closer to Mount Etna, where you can hike, cycle, or use quad bikes to get closer to the volcano. Then make your way back south towards Noto, Syracuse, Ragusa, or Modica. This southeast corner of Sicily has a lot to see, from beautiful rural countryside and vineyards to fantastic beaches. After a few days being shuttled between the beaches or taking fascinating tours, make your way towards Palermo for a couple of nights just outside the city, before flying home.

Where to stay: Four Seasons San Domenico Palace in Taormina is Palazzo-Sicilian at its best, while for a more boutique option, check-in to Hotel Villa Carlotta. Families will relish a break from eye-spy with a few days at Verdura Resort, a Rocco Forte outpost with everything you could ask for. Back in Palermo Villa Igiea (another Rocco Forte hotel), is right on the water’s edge, decorated with Italian antiques and with a gorgeous outdoor pool, it’s the ideal place to see out the end of your holiday.

Puglia

Length: 1 - 2 weeks

Why we love it: Whizz past bright white trulli, olive groves and long sandy beaches on a southern Italy road trip, where the living is easy. Puglia is one of the easiest places in Italy to drive and a good option for families.

Start in Bari (one of the two airport cities in Puglia), making your way south towards Lecce. On the way stop in the picturesque fishermen’s town of Polignano a Mare and the UNESCO Heritage Site of Alberobello to visit traditional trulli houses. Once in Lecce, soak up the sights in the historic city and then push on to the Salento area, where gin-clear waters await. Cool beach clubs, white sand, and turquoise sea make this the ideal location for a few days to unfurl from your car seat and breathe in the salty air.

Where to stay: Borgo Egnazia is one of the loveliest places to stay in Puglia. Rooms are spread across 20 hectares in the style of a typical Apulian town. Further south in Lecce, the boutique hotel Palazzo Bozzi Corso is like a home away from home.

Book Your Italian Road Trip Today

There are no rules when it comes to a road trip in Italy, you can go for as long or as short as you like, packing in stop after stop to see key sights or taking it slowly and savouring the moments. Reach out to our travel experts who will tailor-make the perfect road trip for you.

Milly Darnell

Europe Specialist

Travel has always been a key passion of mine and I am constantly planning my next adventure! I have been lucky enough to visit some fantastic areas and countries all over the world, however I have a strong love of Europe. I often think it is easy to forget about the incredible destinations we have close to home and what a variety these offer and the plus of no jet lag too!

Share this:
You are on our Singapore website
We noticed that you are in US and recommend that you explore our US website instead.
switch to US website
Or continue to explore our Singapore website