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

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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.

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