Boomer Road Trip to Northern Italy on a 9-Day Itinerary

This article may contain referral links. Read our DISCLOSURE

Is an Italy road trip calling your name? If you’ve visited the biggies like Rome, Venice and Florence, it’s time to travel on a boomer road trip to Northern Italy that’s slightly off-the-beaten-path. Fly into Milan, then come along with us on a road trip to Italy that included delightful stops in unexpected Italian destinations.

Rather than drive ourselves, we contracted with Claudio Fontana of Italy A La Carte for a 9-day driving tour of Northern Italy before Claudio delivered us to a cruise ship in  Civitavechhia. If you’re the do-it-yourself type, use this itinerary to create an independent driving tour of the region.

Large white limestone building with a dome
There’s more to Pisa than the Leaning Tower.

Our nine-day boomer road trip began in Milan and ended at Civitavecchia where we boarded Seabourn Sojourn for an Atlantic Crossing, Rome to Ft. Lauderdale. We shared the cost of a private van and guide (Claudia Fontana of A La Carte Italy Tours) with our boomer friends, Jack and Sue.

Claudio hauled our cruise luggage in the van, which saved us the cost of shipping luggage (enough for 21 days including numerous formal nights) to the ship. Alan and I had such a great time that we returned to road trip Southern Italy with Claudio.

Tips for Planning Your Italy Road Trip

Using a guide has its advantages. Alan and I discussed destinations we’d like to visit for this Northern Italian road trip. Claudio offered his opinion, sometimes gently steering us to a better choice.

Once the itinerary was set, Claudio emailed a list of lodging choices for each destination in the category that we had selected (we chose the 4 star option). After checking reviews at TripAdvisor, we notified Claudio of our choices and he made the arrangements, including the hotel price in the cost of his services. If you’re on a do-it-yourself road trip in Northern Italy, start your search for hotels in Italy with us.

When it came time to purchase our flights to Italy (we rode a ship home), we searched for the best rates in flights with Skyscanner. Their apps are especially handy for researching flights while you’re on the road: Skyscanner iOS App Download or Skyscanner Android App Download.

I think it’s essential to purchase travel insurance for international trips. Comparing prices at Insure My Trip is very helpful. And joining an evacuation program like Medjet is also a must in today’s travel climate.

Boomer Travel Tip

We’ll be adding more great road trip ideas for Northern Italy so be sure to bookmark this page. Or subscribe to our weekly broadcast so you’ll be the first to know!

Northern Italy Road Trip Itinerary

From our headquarters at Lake Como, we explored Orta San Giulio and Bergamo. Then we moved on to castle accommodations at La Tavola Rotonda and a day in Italy’s Motor Valley. You do want to drive a Ferrari, right? We spent a day on the coast at Cinque de Terre before peeking behind Lucca’s walls. Are you curious about where Michelangelo found all that marble for his statues? You’ll find exploring a Carrara marble mine. And the grand finale? Spending a night in Southern Tuscany at the Sovana Hotel and Resort. Now that’s a road trip Northern Italy style.

Milan's Duomo

Three Hours in Milan

Although Alan and I are happiest when we’re traveling slow, occasionally we find ourselves cramming as much as we can into a travel experience. That was the case when we stopped in Milan at the beginning of a Northern Italian road trip. Arriving at Malpensa Airport in the late afternoon, we opted for a good […]

Read More >
Charming Orta San Giulio, Italy

Orta San Giulio: Northern Italy At Its Best

Cobblestone streets, a 1580’s era town hall with a frescoed facade, outdoor cafes on a plaza bordering a mountain lake, a fairy tale looking island in the middle of that lake—atmosphere, atmosphere, atmosphere. This is exactly what Alan and I hoped to find on our road trip in Northern Italy. When we told Claudio Fontana […]

Read More >
Medieval Bergamo

Medieval Italy is Alive in Bergamo

On a walking tour of Bergamo, Italy, Alan and I marvel at the stone walls surrounding Città Alta, the upper town of Bergamo, Italy—a medieval city that’s still thriving. In the 17th century, Venetians built the walls to protect the town from Milan. Today, residents and university students live and shop here, dine at local restaurants […]

Read More >
Ferrari test drive in Maranello, Italy

Boomer Adventure in Ferrari Land

Have you dreamed of a Ferrari test drive in Italy? On a road trip in Northern Italy, Alan did just that—while I watched. How did that happen? When it comes to our adventure in Italy’s Motor Valley, there’s no better person to describe it than Alan. After all, he’s the one who actually drove the […]

Read More >
Touring Lamborghini museum

Drooling Over Lamborghinis

If you’re planning a boomer trip to Italy’s motor valley, be sure your itinerary includes the Lamborghini Museum. During our road trip through Northern Italy, Alan may have gotten his kicks test driving a Ferrari, but I’m the one who drooled over the Lamborghini sports cars. The museum’s gleaming concept cars, vintage production models and […]

Read More >
Boomer travel - Italy - stay at La Tavola Rotonda on your boomer vacation in Italy.

La Tavola Rotonda: My Italian Castle

When you think of places to stay in Italy, does a castle come to mind? It does if you’re staying at La Tavola Rotonda.  My idea of castle lodging is a fairytale building perched in the Bavarian hills of Germany, perhaps with snow-capped mountains in the background. I never expected to be sleeping in an […]

Read More >
Cinque Terre

Spend a Day in Cinque Terre

If you only have one day in Cinque Terre, what should boomer travelers see and do? That was the question Alan and I asked ourselves as we planned a road trip in northern Italy. Our guide, Claudio Fontana of A La Carte Italy Tours, came up with the perfect idea. We’d spend a day in Cinque Terre […]

Read More >
Lucca, Italy

Behind The Walls In Lucca

Did you know that Lucca is the only town in Italy to be totally surrounded by walls? Behind those medieval ramparts, Renaissance architecture in the form of churches, elegant shops and picturesque piazzas beckon to be explored.  When Alan and I were planning a road trip to northern Italy with our friends, Jack and Sue, we […]

Read More >
Marble Mountain Lucca Italy

Exploring Inside a Marble Mountain

When you think of visiting Italy, is a Carrara marble mine tour on your boomer itinerary? On a guided road trip in northern Italy, we told Claudio of A La Carte Italy Tours, “the more off-the-beaten-path, the better.” That’s why during our stay in Lucca, Alan and I found ourselves inside a mountain with white […]

Read More >
romantic-sovana-italy

Romantic Relaxation in Tuscany

The end of a long-anticipated trip should leave travelers wanting more, don’t you agree? When Alan and I stepped through the nondescript entry to Sovana Hotel and Resort in southern Tuscany, we discovered a lobby that felt as if we were in an ancient Etruscan wine cellar.  The first words out of our mouths — […]

Read More >
Subiaco, Italy

Italy Travel Planner

Boomers love traveling to Italy, especially when they use our Italy Travel Planner Planning a trip to Italy is both exciting and frustrating. With so many incredible things to see and to do, narrowing your trip down can be a bit overwhelming. To help you with the planning, and hopefully add a bit of inspiration […]

Read More >
Leaning Tower of Pisa

The Best Apps For Italy Travel

Did you know that the best Italy travel app can improve upon your Italian adventure? Whether you’re trying to communicate, checking a train schedule or contemplating which delicious pasta to try, there’s a travel app for that!  I’ve curated the best apps for Italy travel, no matter how you intend to explore this beautiful country. […]

Read More >

Cities to Add to Your Road Trip in Northern Italy

There are so many places to explore in Northern Italy. Here are more cities to add to the itinerary to make the trip uniquely yours. And of course I can’t leave out Rome, Florence or Venice if you haven’t already visited these iconic Italian destinations.

Prato della Valle, Padua, Italy

Strolling through the Top Sights in Padua

As is obvious from our many trips to the country, our love of Italy is pretty much boundless. Fun road trips through the north and south of the country have proved that the country is full of fascinating sites at virtually every corner. Today’s guest contributor, Naomi Elster, is taking us on a history-filled tour […]

Read More >
Bologna travel tips for the first time visitor

Bologna Travel Tips from a First-time Visitor

Italy is undoubtedly one of the world’s most beloved travel destinations. Bustling tourist hotspots like Rome and Florence have dazzled tourists for centuries. But today, we’re taking you to a lesser-known Italian gem that should really be on everyone’s travel bucket list—Bologna. Kris Bordessa from Attainable Sustainable, recently shared her travel tips for Venice with us. […]

Read More >
italy-cortina

Baby Boomer Adventure in Cortina, Italy

Just in time for our trip to Northern Italy. In today’s guest post, Andrew Dunkle advises baby boomers on an active adventure to Cortina, Italy. Hello baby boomer travelers! I am here to take you on an adventure to Northern Italy; Cortina D’Ampezzo to be exact. Located in the heart of the Dolomites, this destination […]

Read More >
Sunset glow over ancient Rome

Baby Boomer Adventures in Rome

If you’re looking for tips on baby boomer adventures in Rome, Italy, you’ve come to the right place. Read on! After covering Italy quite extensively over the years, including writing our Italy Travel Planner, it’s clear that we love to get off the beaten path in this incredible country. However, its capital city is, without […]

Read More >
View from Bell Tower

Exploring Florence

They say that you haven’t really seen Italy until you’ve seen Florence. This gorgeous town is where the Renaissance period began and today, Florence is very much a work of art in itself. Sure, it’s an incredibly popular tourist area, but its full-on Italian splendor and sophistication will leave you breathless nonetheless. Today’s guest contributor, […]

Read More >
man steering a gondola with passengers inside

Travel Tips for Venice from a First-time Visitor

Venice has been a top Italian destination for well, forever. Recently, the city has made headlines for its efforts to crack down on rampant tourism that has overrun the iconic city for decades. However, that doesn’t mean you can’t enjoy a responsible trip to Venice these days. Today’s guest contributor, Kris Bordessa from Attainable Sustainable, […]

Read More >