A Six-Week Italy Road Trip Itinerary

An Epic 40-day Drive With Dick & Jane

Travel Guide - Itinerary

Follow John and Rae’s epic journey discovering Italy on a six-week road trip — from the Amalfi Coast to as far north as The Dolomites to a mix of Italy’s lively cities, cosy towns, and traffic-free villages, to everywhere in between.

Italy Road Trip - May 2017

In May 2017, I introduced my husband, John, to Italy. I hadn’t visited Italy since I was a young backpacker some 25 years earlier.

For well over a decade, Asia had traditionally been our go-to destination. Initially, Europe was considered a far-flung destination from Australia and a long way from our financial reach.

After some soul-searching, we took the plunge and started researching all the possibilities. We started looking at visiting the most popular western European locations. Generally, we knew we would be touching only the surface of what all these Italian ancient cities and regional towns had to offer.

The idea to travel exclusively around Italy, with an attitude of doing it right the first time or not at all, gave birth to us emerging ourselves full throttle into all things Italian. Starting with the concept of four weeks, this quickly grew to six.

Our six-week holiday driving around the Italian countryside was going to be one of the most logistically extensive road trips we had undertaken at the time.

Two years later, we repeated our passion for road tripping, driving around the Greece mainland, the Cyclades Islands, and Crete as part of our 5-week Greece, Italy and Turkey itinerary.

Naturally, Covid put a drastic halt to everyone’s travels for a couple of years. But, come 2023 we are returning to Italy and the Mediterranean to conclude our Italy road trip adventures. This time to Sardinia and Sicily, and spending more time this trip in the heart of Tuscany.

Countdown to D-day

A date set two years out from our departure day (D-day) dictated our timeline of things to do moving forward.

Bucket List of Experiences

Besides the typical tourist most popular hotspot Italy locations, the Dolomites were on my bucket list.

As an avid landscape photographer, I wanted to be on the plateau of Alpe di Siusi, Dolomites by end-May. This month is the season when the cable-cars reopen, after a winter hibernation. Time to relish in panoramic views across the alpine meadows and take macro photos of the first blossoming of  spring wildflowers.

Hiking the Alps is not the only activity we ticked off our Italy bucket list.  View our bucket list highlights below as to what we accomplished over our journey throughout Italy.

Transport

As independent travellers, not having to line up for a coach bus and being dictated by a schedule was appealing.

John loves nothing better than to get behind the wheel of a car on a road trip away from the well-worn tourist path. There is nothing like the screech of the brakes, as his partner in crime, me, wants him to pull over for a photographic opportunity, roadside farmers stall or landmark that grabs my attention. 

Accommodation

When researching to find and book accommodation, we tried to vary the location, style, budget, star-rating (3+) and reviews (8+) of the places to stay. The accommodation we chose required free or garage car parking (parcheggio) to house securely our leased car.

Throughout our Italy road trip, we stayed in 16 hotels, bed and breakfasts and Agriturismi countryside establishments.

Check out our list of recommended places and our travel reviews. In hindsight, booking earlier boutique family-run places (that also included a mini-bar fridge – not common in Italy) is more our travel style. These places ooze Italian warmth and hospitality, personalised service and fantastic locations.

Spring wildflowers on the Alpe di Siusi, Dolomites, Italy
Spring wildflowers on the Alpe di Siusi, Dolomites, Italy
Views from Villa Monica B&B
Views from Villa Monica B&B, Sorrento, Italy

Budget and Savings Ideas

Before and during your Italy trip, there are many ways to save time and money. For example:

  • Compare flights with airlines and sleep in budget-style accommodation in good locations.
  • Travel during off-peak (cheapest) and shoulder (cheaper) seasons. Note: May is considered in Italy one of the best and busiest travel months. Crowds aside, this month combines the convenience of being a shoulder season with pleasant weather.
  • Eat local and off-the-beaten tourist paths or pack a picnic from produce markets and family-run stores.
  • Take self-guided walks to tour cities and towns instead of hiring a professional guide.
  • Purchase day-passes for discounted admission fees to popular sites, art galleries and museums with the added benefits of skipping the long queues.
  • Read website travel blogs and guidebooks for valuable tips, tricks and hacks and download essential travel apps.

Visit our RESOURCES section for tips, hacks and informative budget-saving travel guides, templates and checklists.

Stepping Outside your Comfort Zone

We stepped outside our comfort zone and immersed ourselves amongst the locals, unfamiliar with the language or locality. In doing so, we stopped being the typical tourist but became travellers with a flexible daily itinerary and a wanderlust open mind to discovering new experiences.

Language

Six months before we left on holiday, we made a concerted effort to learn the Italian language, listening to free apps for mobile devices like Duolingo.

After six weeks in the country, we spoke five-word sentences that made sense to the locals. Grazie Mille. Il tuo cibo ha un sapore fantastico.  In future, we are planning to trial and review Language Translator Earbuds currently in the marketplace.

Going Off the Beaten Tourist Path

Going on back road nature walks, hiking trails and detouring via goat tracks can have their rewards.

We discovered fine-dining restaurants (ristoranti). Gem holes in-the-wall restaurants (trattoria) that screamed Nonna’s home cooking. Casual eateries (osteria) and bars (barre) where all the locals ate and drank.

Most of all, we got off the beaten path and walked that little further away from the main tourist strip or got deliberately lost to see where we would end up.

Rae tastes a shot of the local Limoncello for the first time like a Virgin Mary!
Rae tasts a shot of the local Limoncello like a Virgin Mary!
In Rome Italy, John wines and dines like a local.
In Rome Italy, wining and dining like a local.
Blessed with views of the Gulf of Naples, Sorrento Coast and Mount Vesuvius.
Blessed with views of the Gulf of Naples, Sorrento Coast and Mount Vesuvius.
John chuffs on a cigar in St Mark's Square, Venice, Italy, while listening to orchestral music.
John chufs on a cigar in St Marks Square Venice whilst listening to orchestral music.

Itinerary (Sneak Peak)

Our Italy trip commences with us driving down to the seaside resort port of Sorrento, having spent four nights car-free in the Eternal City of Rome. Heading south on the winding scenic coastal Amalfi Drive we reached our next stop Ravello. Back on the road, we drove northbound on the A1 freeway to the green heart of Italy’s Umbria region to visit places such as Orvieto, Civita and Assisi. Followed by stops at several key locations in the heart of Tuscany, such as Montepulciano, Pienza and Montalcino.

Our Italy itinerary also ticked off our location bucket list of the nine most popular places to visit in Italy (excluding Sicily and Sardinia which we visited in 2023) and other Italian villages and towns that grabbed our attention.

Map of Italy by Region and Locations
Map of Italy

Lessons Learned

In the process of planning our Italy road trip, we learnt a great deal not only about ourselves travelling as a couple but also:

  • How to have a prosecco holiday on a beer budget.
  • Taking a DIY approach to free self-guided walking tours around Italy.
  • How to sift through the noise and evaluate TripAdvisor and other review-related booking sites.
  • Use Pinterest to obtain inspiration and plan our next holiday destination.
  • Take advantage of Italy’s tourist discount cards and passes.
  • Research top tourist attractions and activities in Italy directly via local tourism boards and travel blogs.
  • Effective ways to find the best rates for hotels online.
  • Become research savvy and find the best airfare deals.
  • Save money on car leasing instead of renting.
  • Join loyalty card and frequent flyer membership programs to access discounts and other member benefits.
  • Watch YouTube for traveller reviews and how-to’s.

Through our simple downloadable checklists and how-to travel guides readily available on our blog, we’ve collated all our learnings to educate you on becoming a confident and independent traveller.

Leasing A Car

40 days: Southern and Northern Italy (4,000km)

We chose to lease a Peugeot 309 auto 4-cylinder 5-door hatchback for 34 days of our 40-day itinerary.

The car we nicknamed, tongue-in-cheek, DICK.  Our leased car comfortably accommodated 2-4 passengers. The Peugeot included for free the English-speaking female sultry tones of our GPS. We called her JANE. The in-built GPS was a god-send for navigating short-cuts, finding the nearest Auto-grill gas stations and taking us on freeways, byways and roads less travelled.

To find out how, view our post on The Essential Guide to Leasing (or Hiring) a Car in Europe.

PICK UP: Rome  DROP-OFF: Rome

John and I stop to admire the majestic views on our scenic drive to Prionia, Mount Olympus, Greece.
In Rome Italy, wining and dining like a local.
Ravello, Italy, driving in our leased car through a ZTL (with a permit) to get to our hotel.
Blessed with views of the Gulf of Naples, Sorrento Coast and Mount Vesuvius.

Best Time to Visit

Climate

Mid-April to mid-June is the peak season to visit Italy to experience pleasant warm weather and to take advantage of the long daylight hours. 

Compared to Australia’s 30-35 degrees Celsius tropical humid climate, Italy’s mild 20-25 degrees temperatures during spring/summer were heavenly.

Travel Seasons

Italy has three distinct travel seasons. From peak season (mid-June through August) to shoulder season (April through mid-June and September through October) to the off-season (November through March).

Striking the right balance of seasonal timing and finding inexpensive accommodation centrally located (with car parking) to experience each city and town was challenging, but essential. 

A desire to avoid the tourist crowds and traps within reason, was also high on our decision-making process. To enjoy key tourist sites without these hassles requires you to, at times, get up early or stay up late – well after the crowds, buses and cruise ships have departed.

Cool off with a swim on the Isle of Capri, Italy
Cool off with a swim on the Isle of Capri, Italy
Riomaggiore, Cinque Terre Italy
Avoiding the peak season crowds during May when hiking the Cinque Terre, Italy.

Bucket List Highlights

  • Hike the trails and enjoy the views of the Cinque Terre.
  • Learn how to make pasta in a small-group cooking class.
  • In Naples, devour a Margherita pizza.
  • See Michelangelo’s Statue of David in Rome, Da Vinci’s Last Supper in Milan, Botticelli’s Birth of Venus in Florence and countless fine pieces of Italian art and architecture.
  • Accompany my Catholic husband, John, to St Peter’s Basilica in the Vatican to make a prayer and see the Pope. Amen!
  • Try limoncello, grappa and other Italian cocktails and spirits. And, let us not talk about the wine and vineyard wine tasting and consuming a bottle (or two) of vino regularly over a 3-course Italian fiesta.
  • Toss a coin in the Trevi Fountain for good luck.
  • Take a gondola ride down the Grand Canal and pass the Rialto Bridge in Venice.
  • Drive the Amalfi Coast (and over 4,000 km all around Italy).
  • Pompeii and its ancient ruins and treasures.
  • Take a ferry to Capri and ride a Vespa around the island.
  • Swim in the Blue (and Green) Grotto.
  • Lick a cone of gelato daily.
  • Tour Rome Colosseum and Forum and the Pantheon.
  • Eat ridiculous amounts of pasta, bread and pastries.
  • Take a boat ride on Lake Como. Plus, wave an Australian ‘gidday’ at George Clooney as we passed his summer home villa.
  • Go wine tasting and consume a bottle (or two) of vino daily.
  • And so much more.

What is on your Italy travel bucket list? What places have you been? What memorable adventures in Italy have you experienced? If you are a first-timer to Italy, I trust our bucket list inspires and challenges you to start ticking them off your wish list. Would you like to know more about our trip to Italy? Then contact us.

Magic Moments

location_on Italy Enjoy the Daily Intake of Gelato with Gusto location_on Certaldo Make Pasta Like a Nonna at a Tuscany Cooking Class location_on Italy Taste a Drop of the Local Limoncello and Grappa location_onFlorence See Michelangelo's Statue of David in all his Glory location_on Pompeii Explore the Ruins of Pompeii with Mount Vesuvius on the Horizon location_on Cinque Terre Hike the Five Riviera Hamlets of the Cinque Terre location_on Florence Admire the Renaissance Artworks of Florence's Uffizi Gallery location_on Venice Cruise the Canals of the Floating City of Venice Enjoy the Daily Intake of Gelato with Gusto 3 Make Pasta Like a Nonna at a Tuscany Cooking Class 1 Taste a Drop of the Local Limoncello & Grappa 2 See Michelangelo's Statue of David in all his Glory 4 Explore the Ruins of Pompeii with Mount Vesuvius on the Horizon 7 Hike the Five Riviera Hamlets of the Cinque Terre 5 Admire the Renaissance Artworks of Florence's Uffizi Gallery 6 Cruise the Canals of the Floating City of Venice 8

FREEWAYS, BYWAYS AND ROADS LESS TRAVELLED

Our Italy road trip stats.

  • 4,000km in Italy driving the car.
  • Sixteen places we temporarily called home, from hotels to villas to refurbished B&Bs Agriturismi.
  • Exploring 50 cities, towns and villages (not counting the ones we stopped via for coffee and croissants).
  • Hiking 1 million cobbled-stone steps (thank god – otherwise, I would be asking the air hostess, “can I have the seat belt extension, please!”
  • Climbed hundreds of thousands of undulating stairs to reach the pinnacle and panoramic hilltop views and landscapes.
  • Enjoyed meeting countless wonderful Italians, from villa hosts to tour guides to other random strangers from around the world.
  • Eating Italian cuisine guilt-free (including at least a cone of gelato and a bottle of vino per day) with a passion for food and the pleasure of each other’s company.

Asked often was what was our favourite place in Italy.

For us, it wasn’t the places we had visited but the people we met, the little moments in time that made an impression or made us laugh out loud.

Check out our The Essential Guide to Leasing (or Hiring) a Car in Europe and other related articles on Italy below.

An Australian couple driving a French leased car throughout Italy. What are the odds?
An Australian couple driving a French leased car throughout Italy. What are the odds?

Italy Itinerary - Part 1

Subtitle

Week 1

Day 0: Brisbane, Australia flight to Abu Dhabi, United Arab Emirates (UAE) (Flight: 14 hr 35 min).

Day 1: Abu Dhabi, UAE. Sleep in Abu Dhabi 2 nights stopover en route to Rome.

Day 2: Abu Dhabi to Dubai and return. Pick-up rental car. Self-guided road trip. (Drive: 140 km, 1 hr 17 min one way)

Day 3: Abu Dhabi, UAE to Rome, Italy (Flight: 6 hr 45 min).  Afternoon at leisure to explore the beating heart of Rome. Sleep in Rome 4 nights.

Day 4: Rome – Free day to experience the Rome’s neighbourhoods and enjoy its food and wine culture.

Day 5: Rome – Free day to discover ancient Rome.

Day 6: Rome – Free day to visit Christian Rome and the Vatican City.

Day 7: Rome to Sorrento via Pompeii.  Pick-up leased car near near Rome’s Fiumicino airport. Sleep in Sorrento 4 nights. (Drive: 268 km, 3 hr 22 min)

Week 2

Day 8: Sorrento – Free day to explore the cliffside resort town of Sorrento.

Day 9: Sorrento – Isle of Capri day trip by ferry.

Day 10: Sorrento – Naples day trip by ferry.

Day 11: Sorrento to Ravello, Amalfi Coast via Positano. Sleep in Ravello 2 nights. Rest of the day free to explore the lush green hill town of Ravello. (Drive: 39 km, 1 hr 33 min)

Day 12: Ravello – Free day to hike the trails down to Altrani and Amalfi Town.

Day 13: Ravello to Orvieto, Umbria via Civita di Bagnoregio. Sleep in Orvieto 3 nights. (Drive: 391 km, 4 hr 49 min). Rest of the day at leisure to visit Umbria’s grand hill town and church.

Day 14: Orvieto – Free day to discover South Umbria by car.

* Travel times and distances are approximate only, may take into consideration scenic and non-direct driving routes, and don’t include time for stops along the way.

Week 3

Day 15: Orvieto – Free day to discover East and North Umbria (incl. Assisi, Spello, Perugia) by car.

Day 16: Orvieto to Pienza, Tuscany. Sleep Pienza 1 night. (Drive: 80 km, 1 hr 14 min). Optional self-drive the scenic loop around Tuscany’s Val D’Orcia region and Brunello wine country.

Day 17: Pienza to Certaldo, Tuscany. Sleep Certaldo 4 nights. (Drive: 98 km 1 hr 31 min)

Day 18: Certaldo – Free day to drive the Chianto Classico region.

Day 19: Certaldo – Free day to explore Etruscan villages by car.

Day 20: Certaldo – Free day to day trip around Siena and surrounds.

Day 21: Certaldo to Florence, Tuscany. Sleep Florence 3 nights. (Drive: 54 km, 52 min) Take a self-guided walk around Florence including the Duomo, its Bapistry and sights in the Oltrarno (south of the Arno River).

Italy Itinerary - Part 2

Week 4

Day 22: Florence – Free day to either take a food tour, go shopping or visit the street markets.

Day 23: Florence – Free day to explore all the Renaissance art galleries, museums and churches.

Day 24: Florence to Venice via Bologna. Sleep in Venice 3 nights (Drive: 262 km, 3 hr 23 min). Afternoon for Venice orientation and an evening on a Jewish Ghetto food and wine tour or go on a Chicchetti bar crawl.

Day 25: Venice – Cruise the Grand Canal, go on a gondola ride, take a self-guided walk around Venice including St Mark’s Basilica and Doge’s Palace, and have an evening in St Mark’s Square listening to orchestral music.

Day 26: Venice – Free day to take the local vaporetto to see the four Lagoon islands: San Michele, Murano (glassmaking), Burano (lacemaking), and Torcello.

Day 27: Venice to Kastelruth/Castelrotto, the Dolomites via Bolzano. Sleep Castelrotto 3 nights. (Drive: 294 km, 3 hr 21 min)

Day 28: Hike to the wildflower-speckled meadows of the Alpe di Siusi, the Dolomites.

Week 5

Day 29: The Dolomites – Free day to discover the many hiking trails in the area.

Day 30: Kastelruth/Castelrotto to Varenna, Lake Como via Verona. Sleep in Varenna 2 nights. (Drive: 351 km, 4 hr 33 min). Rest of the afternoon to relax and explore the romantic village of Varenna.

Day 31: Varenna – Free day to explore Lake Como. Optional take the battello navetta (mid-lake ferry) on its entire 50-minute Varenna-Bellagio-Villa Carlotta-Tremezzo-Lenno route, and hop on-and-off to any of these lakeside towns.

Day 32:  Varenna to Stresa, Lake Maggiorre via Lugano (Switzerland). Sleep Stresa 1 night (Drive/Car Ferry: Varenna to Menaggio 5.4 km, 38 min + Drive: 144 km, 2 hr 18 min). Stresa orientation and optional tour of Borromean Islands.

Day 33:  Stresa to Milan. Sleep in Milan 2 nights. (91 km, 1 hr 25 min). Explore the fashion capital Milan and take a tram ride to the Navigli District for apertivo and dinner.

Day 34: Milan – Free day to go shopping and tour Milan including a visit to Da Vinci’s Last Supper and Santa Maria delle Grazie Church.

Day 35: Milan to Santa Margheria Ligure, The Italian Riviera. Sleep in Santa Margheria Ligure 1 night. (168 km, 2 hr 7 min). In the afternoon take a short ferry ride to visit nearby Portofino and take a scenic hike or bus ride back to home-base.

Week 6

Day 36: Santa Margherita Ligure, Genoa to Monterosso al Mare, Cinque Terre. Sleep in Monterosso 3 nights (Drive: 87 km, 1hr  43 min). Local orientation of Monterosso harbour and town centre.

Day 37: Cinque Terre – Free day to explore either by train or via the hiking trails connecting Manarola and Riomaggiore.

Day 38: Cinque Terre – Free day to explore either by train or via the hiking trails connecting Vernazza and Corniglia.

Day 39:  Monterosso, Cinque Terre to Lucca. Sleep in Lucca 1 night. (Drive: 110 km, 1 hr 49 min). Take a self-guided walking tour of Lucca, cycle around Lucca’s citadel walls and spend an evening listening to a Puccini Opera performance.

Day 40:  Lucca to Rome via Pisa. Visit the Leaning Tower of Pisa. Drop-off leased car near Rome’s Fiumicino airport before taking international flight home (Drive: 361 km, 4 hr 10 min).

* Travel times and distances are approximate only, may take into consideration scenic and non-direct driving routes, and don’t include time for stops along the way.

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