Culture, cuisine, and coasts: incredible road trips through Italy

Italy’s diverse geography is perfect for road trips. This elongated country stretches 736 miles from northwest to southeast, with its extremes resembling two distinct nations. No matter your chosen route, you’ll always be close to the coast and the chance to dip into one of its three seas—the Adriatic, Ionian, or Tyrrhenian. Along the way, you’ll discover some of the world’s most remarkable cities, perhaps the finest cuisine on the planet, and an abundance of culture waiting to be uncovered. A road trip in Italy is a delightful sensory journey.

What’s the best way to reach Italy from the US?

Italy’s configuration makes your choice of airport essential depending on your road trip destination. For northern trips, Milan is the premier choice for flying in from the US, with the contemporary Milan Malpensa airport being the second largest in Italy. The capital, Rome, is nearly equidistant between the north and south and has the largest airport in the country, Leonardo da Vinci-Fiumicino. Regular direct flights are available from major US cities to both Milan and Rome, making them the most convenient gateways.

For those venturing further south, you can also fly directly to Naples, which is ideal for exploring the famous Amalfi Coast. And let’s not overlook Sicily—the island that Italy's boot is kicking. Both Palermo and Catania airports are a short flight from Milan and Rome, with regular car ferries linking it to the mainland in about 20 minutes. Plus, it’s stunningly beautiful.

What type of vehicle is best for a road trip in Italy?

Like much of Europe, Italy’s roads and highways are generally in excellent condition and don’t require any special vehicle considerations. While you may encounter some rougher paths off the tourist trail (especially in Tuscany and the far south), they’re usually manageable. Select your rental based on your budget and your travel companions.

What’s the ideal time for an Italy road trip?

Italy’s climate varies greatly from north to south and from season to season, making it essential to carefully plan your road trip itinerary and travel dates.

In the northern part of Italy, which borders Austria, Switzerland, and France (among others), the region is embraced by the Alpine and Dolomite mountain ranges. Here, you’ll discover the stunning lakes of Como and Garda, as well as major cities like Milan, Venice, and Bologna. The weather can fluctuate from hot and sunny to cold and snowy, so the best time for a road trip in northern Italy is from late spring to early fall. Flight data from Dinogo shows that Milan experiences its peak traffic in May, April, and June.

As we move south into the central regions, we travel through Florence and the picturesque hills of Tuscany down to Rome and Naples. The weather here is generally milder, with average temperatures in Rome exceeding 60°F from May to October, reaching a high of 74° in July and August (data sourced from weatherbase.com). Rainfall is minimal, averaging less than an inch per month during the summer. Like Milan, Rome also sees its busiest travel months in May, April, and June, while August tends to see fewer visitors as tourists try to steer clear of the sweltering summer heat.

The toe of Italy's boot leads to beautiful Bari, navigating through the Puglia and Calabria regions and ultimately reaching Sicily. Located near Africa, this area enjoys a warm climate year-round, though it can become uncomfortably hot during the peak summer months.

June is my preferred month for an Italian road trip. It strikes a perfect balance between pleasant weather, manageable crowds, and ease of travel. While some locations are bustling all year, in June you can explore tourist hotspots at your leisure.

What is the cost of a road trip in Italy?

Before making your travel plans, it's helpful to estimate the expenses for a road trip in Italy. Here are some figures for your reference, compiled by comparing numerous travel providers.

Discover the north: a 7-day road trip through Italy

Italy’s northern region is a paradise for road trippers, offering a rich tapestry of mountains, lakes, and vibrant cities. You could explore its picturesque roads for months and still find new adventures. Here’s how to experience it in just seven days.

Day 1: Milan

Milan thrives on fashion, food, and finance. Immerse yourself in this vibrant city before heading east. If you do just one thing, make it a visit to see Da Vinci’s The Last Supper at the Santa Maria delle Grazie convent—an essential glimpse of historic Milan.

Where to stay in Milan: The Hotel Magna Pars offers a serene five-star retreat right in the fashion district, complete with parking.

Day 2: Lake Como

Distance from Milan: 52 miles

Lake Como resembles a postcard come to life. Drive along its edge through charming lakeside towns filled with neoclassical villas and the occasional Hollywood celebrity. Make sure to stop in Bellagio, Varenna, or Como for a leisurely lunch that often flows into a long evening. You can also hop on one of the local ferries to take in the tranquil views of the surrounding mountains.

Where to stay around Lake Como: Accommodations can be pricey, which makes B&B Villa Rosalinda a remarkable find at an affordable rate.

Day 3: Verona

Distance from Lake Como: 111 miles

For a romantic getaway, Verona is an ideal stop. Known as the backdrop for Shakespeare's tragic tale, Romeo and Juliet, you can explore the famous Casa di Giulietta, Juliet's House.

Where to stay in Verona: For a romantic ambiance and a prime location, consider Relais Balcone di Giulietta.

Day 4: Venice

Distance from Verona: 75 miles

No introduction is needed for Italy's enchanting floating city. Wander through historic palaces and picturesque piazzas, glide along magical canals in a gondola, and admire the Basilica, the Bridge of Sighs, and countless other breathtaking sights. Immerse yourself in its rich history and culture.

Where to stay in Venice: Praised for its service and prime location, La Veneziana Boutique Rooms offers an affordable yet delightful stay.

Day 5: Cortina d'Ampezzo

Distance from Venice: 99 miles

Just two hours north of Venice, you’ll enter the UNESCO World Heritage site of the Dolomite Mountains. This stunning natural playground offers a wealth of activities including hiking, climbing, biking, and skiing, depending on the season. It also features some of the most breathtaking mountain passes you can drive through.

Where to stay near Cortina d’Ampezzo: Experience the charm of Hotel Villa Alpina, a cozy wooden retreat nestled in the mountains.

Day 6: Lake Garda

Distance from Cortina d’Ampezzo: 201 miles

Italy's largest lake beautifully blends culture and adventure. Drive through charming lakeside towns like Sirmione, Garda, and Malcesine. Enjoy sailing and windsurfing on the lake, or opt for a leisurely scenic tour.

Where to stay in Lake Garda: Experience stunning lake views and a beautiful terrace at Hotel La Dolce Vita.

Day 7: Lake Orta

Distance from Lake Garda: 132 miles

If you prefer not to spend another night in Milan, consider heading to the charming Lake Orta, my personal favorite among the Italian lakes. It's tranquil and sophisticated, offering a beauty that is less glamorous yet equally captivating—perfect for concluding an unforgettable road trip.

Where to stay in Lake Orta: Casa Fantini is a delightful family-run retreat that truly embodies the essence of 'Lake Time'.

North to south: the ultimate two-week road trip through Italy

If you have the time and are ready for an adventure, embarking on a road trip through Italy offers a unique experience. With landscapes and cultures that continually evolve, set against a backdrop of delicious cuisine and extraordinary historical sites, this journey starts and ends in different cities.

Day 1: Milan

Similar to my seven-day itinerary, Milan is the ideal starting point for your journey. Fly directly from the US and be sure to dedicate at least a day to explore its countless treasures.

Day 2: Portofino

Distance from Milan: 122 miles

Travel south to the idyllic fishing village of Portofino, nestled in a stunning cove along the Ligurian Sea. Enjoy a swim and then take a leisurely stroll past its charming pastel-colored houses and fashionable waterfront eateries.

Where to stay in Portofino: The historic Hotel Piccolo Portofino offers a private beach and stunning balcony views.

Day 3: Cinque Terre

Distance from Portofino: 45 miles

While Cinque Terre National Park isn’t car-friendly, the visit is undeniably worthwhile. Its five stunning coastal villages are steep and breathtaking, interconnected by the Sentiero Azzurro cliff trail. You can stay outside the park in La Spezia and take the train in, or drive directly to Monterosso al Mare, the largest town.

Where to stay around Cinque Terre: The simple yet satisfying La Rosa Dei Venti is just meters from the beach and offers excellent value.

Day 4: Pisa

Distance from Cinque Terre: 75 miles

With just one day to spare, your mission is clear: head to the Campo dei Miracoli, or Field of Miracles, and perfect your leaning tower pose.

Where to stay in Pisa: The luxurious Lungarno Buozzi 7 Apartments are centrally located and offer on-site parking.

Days 5 & 6: Florence

Distance from Pisa: 53 miles

The Renaissance City deserves a minimum of two days, but any enthusiast of art and culture could easily spend weeks exploring. You'll have the chance to visit major attractions like Palazzo Vecchio, the Duomo, Pitti Palace, and the remarkable Uffizi Gallery. Compact and pedestrian-friendly, you'll absorb centuries of history in a way that few cities can offer.

Where to stay in Florence: The Corte Calzaiuoli Elegant Suites boast a prime central location and are the highest-rated on Dinogo.

Day 7: Siena

Distance from Florence: 50 miles

Driving through Tuscany is a delight—think warm pastel landscapes, medieval hilltop castles, and perfectly aligned cypress trees that characterize the region. Siena stands out as perhaps the most beautiful of its towns. Be sure to visit the Piazza del Campo, one of Europe’s most magnificent medieval squares.

Expert tip: The Val d’Orcia region, located south of Siena, is my choice for Italy’s most picturesque drive. Consider extending your stay by a night at the lovely Locanda in Tuscany, a charming boutique hotel set in a former farmstead.

Day 8: Montepulciano

Distance from Siena: 40 miles

Renowned for its exquisite wine, Montepulciano offers a rustic, authentic experience and is an excellent spot to sample the finest Tuscan produce. If time allows, treat yourself to the nearby hot springs at Bagni San Filippo to unwind after your travels.

Where to stay in Montepulciano: The serene and inviting Hotel I Due Cigni is a fantastic value, with discounts available for the nearby thermal baths.

Day 9: Assisi

Distance from Montepulciano: 55 miles

A small detour on your way to Rome, Assisi is well worth the extra distance. As the birthplace and final resting place of St. Francis, it embodies charm with its geranium-scented, cobblestone streets that ascend to breathtaking viewpoints near the hilltop basilica. Look out for its impressive silhouette as you approach – it dominates the landscape – and be prepared for a bustling crowd of tourists and pilgrims.

Where to stay in Assisi: The Brunelli B&B features a stunning courtyard, ideal for enjoying a delightful breakfast.

Days 10 & 11: Rome

Distance from Assisi: 109 miles

The grandeur and richness of Italy's capital are beyond words. Known as the Eternal City for good reason, it serves as a sprawling interactive museum, showcasing the creativity, culture, and resilience of humanity over millennia. Stroll its streets, explore its most remarkable landmarks, and allow yourself to be awed.

Where to stay in Rome: The Villa Agrippina Gran Meliá offers a tranquil five-star retreat just steps from Vatican City.

Days 12 & 13: Amalfi Coast

Distance from Rome: 173 miles

Though the Amalfi Coast is just 34 miles long, it offers a road trip experience all its own (one of my personal favorites, especially in the off-season). The winding roads cling to cliffs, linking stunningly glamorous towns where affluent Europeans enjoy leisurely lunches beneath clear blue skies. While Positano attracts many visitors, I find the more tranquil and sophisticated Praiano and Conca dei Marini even more appealing.

Where to stay along the Amalfi Coast: Hotel Le Terrazze boasts breathtaking sea views on the edge of Conca dei Marini.

Day 14: Napoli

Distance from Amalfi Coast: 39 miles

As the birthplace of pizza, Naples serves as your final destination (unless you're embarking on a month-long adventure!). This vibrant city has a rugged charm. On your return from the Amalfi Coast, make sure to visit Pompeii to wander through the world’s best-preserved Roman ruins, a legacy of Mount Vesuvius. Afterward, indulge in the city’s iconic pizza—it's a well-deserved treat!

Where to stay in Napoli: One of the finest new upscale B&Bs is The Dante House.

How does Dinogo curate this guide?

Few places in Europe captivate me as much as Italy. From my initial explorations in the north, driving down from Germany, to leisurely summer journeys along its stunning coast, Italy has enchanted me. This road trip guide is a tapestry of those adventures, connecting incredible destinations along some of the most scenic routes.