This Is How We Planned Our 6-Day Tuscany Road Trip

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Why We Chose Italy

As I mentioned in my Tromsø article, my friends and I try to plan one girls’ trip somewhere in the world every year.

I had been to Italy before, specifically Rome, but that was many, many years ago. In fact, it’s been so long that I don’t think I’ll write about Rome until I visit it again. They do say that all roads lead to Rome, and somehow I feel like that’s true.

This time, however, we wanted to experience a completely different side of Italy.

Instead of returning to the busy streets of Rome, we decided to explore the north of the country, focusing on Tuscany, its famous hill towns, vineyards, and beautiful countryside roads.

And of course, let’s be honest… the pizza definitely played a part in the decision.

Our plan was simple: rent a car, spend six days driving through some of Tuscany’s most iconic destinations, eat as much Italian food as possible, and enjoy a mix of historic cities, stunning landscapes, and plenty of spontaneous stops along the way.

Our 6-Day Italy Road Trip Route

We started and ended our road trip in Milan, which made it easy to pick up and return our rental car directly at the airport.

I flew from Oslo via Copenhagen to Milan, while my friends from Athens found a great deal on a direct flight to Bergamo. They spent a night there before driving to Milan Airport to pick me up, and from that moment, our Tuscany adventure officially began.

The plan was simple: use Florence as our base and spend the following days exploring Tuscany’s famous cities, charming villages, and scenic countryside roads.

Our itinerary looked like this:

Day 1: Milan → Piacenza → Parma → Florence

Day 2: Florence

Day 3: Siena → San Gimignano → Florence

Day 4: Pienza→ Florence

Day 5: Pisa → Milan

Day 6: Explore Milan & Fly home from Bergamo Airport

We deliberately chose not to spend time in Milan at the beginning of the trip. Since our flights home were departing from there anyway, we thought it made more sense to dedicate our first days to Tuscany and save Milan for the end.

Looking back, that decision had both advantages and disadvantages.

I’ll explain why later in the article, but overall, I still think it was the right choice for this itinerary.

In the next sections, I’ll walk you through each day of the trip, share what we loved, what we would do differently, and whether I would recommend this exact route if you’re planning your own Tuscany road trip.

Day 1: Milan to Florence (with a Stop in Parma)

After landing in Milan and picking up our rental car, we immediately started our drive towards Florence.

Along the way, we passed through Piacenza, Parma, and Bologna, getting our first glimpse of the Italian countryside.

By the time we arrived in Florence, it was already evening, so we decided to keep things simple. We went out for dinner, enjoyed our first Italian meal of the trip, and then headed back to the hotel to get some rest before the days ahead.

One thing we made sure of when booking our accommodation was choosing a hotel with parking.

We did the same in our road trip in Costa Rica. If you’re planning a similar road trip, I highly recommend doing the same because it will save you both time and stress.

Italy is famous for its strict driving regulations and expensive traffic fines. Rather than making this article too long, I will write a separate guide covering everything we learned about driving in Italy, including ZTL zones, parking, toll roads, and the mistakes you’ll definitely want to avoid.

Day 2: Exploring Florence

We started the day with breakfast at our hotel before heading into Florence’s historic centre.

Although we had a rental car, we deliberately left it parked.

Florence is one of those cities that’s best explored on foot, and you can’t drive or park in many parts of the historic centre anyway.We spent the entire day wandering through the beautiful streets, admiring the architecture, crossing historic squares, and stopping every few minutes to take photos.

Honestly, every corner looked like something out of a movie.Florence has a unique charm. It feels like an open-air museum, yet at the same time it’s lively, authentic, and full of local life.

Whether you’re sitting in a piazza with a coffee or simply getting lost in the narrow streets, the city has a way of making you slow down and enjoy the moment.

By the end of the day, we completely understood why Florence is considered one of the most beautiful cities in Italy.

Day 3: Siena & San Gimignano

On our third day, we visited Siena and San Gimignano.

Siena quickly became one of my favourite places of the entire trip.

The architecture, the narrow streets, the rolling hills, the colourful balconies filled with flowers and hanging laundry, everything felt like a movie set.

We spent a few hours wandering through the city, taking countless photos, and enjoying a delicious pizza while overlooking the historic centre. Honestly, I could have spent an entire day just getting lost in its streets.

Later, we continued to San Gimignano, a small medieval town famous for its towers and incredible atmosphere.

Our main mission?

Trying the world-famous, award-winning gelato from Gelateria Dondoli.

Was it worth the hype?

Absolutely.

The ice cream was fantastic, but honestly, the town itself completely stole the show. Walking through the stone streets, browsing the small local shops, and admiring the medieval towers felt like stepping back in time.If you’re planning a Tuscany road trip, I genuinely wouldn’t skip either of these places.

They ended up being two of the biggest highlights of our journey.

Day 4: Florence & Pienza

We spent another day based in Florence, with a short trip to Pienza during the day.After exploring the area, we returned to Florence for one last evening walk through the city.

Since it was our final night in Tuscany, we wanted to enjoy it as much as possible before heading back to Milan the next day.

There is something magical about Florence after sunset.

The crowds become smaller, the streets feel calmer, and the whole city has a completely different atmosphere. It almost feels like a different place compared to the busy daytime.

We grabbed one last dinner, enjoyed one last gelato (because… when in Italy, right?), and simply wandered around without any plan.

It was the perfect way to say goodbye to Tuscany before beginning our journey back north.

Day 5: Pisa & Return to Milan

On our way back to Milan, we made a stop in Pisa.

The Leaning Tower is definitely the main attraction, and yes, we took the classic tourist photos like everyone else. I don’t think anyone leaves Pisa without at least one picture pretending to hold the tower!

Unfortunately, it rained heavily during our visit. At that point, I was starting to think I might actually be cursed when it comes to the weather. The exact same thing happened during our trip to Lisbon later on.

Apparently, rain just likes to follow me around.Still, no regrets.Even with the rain, Pisa was a fun stop and a great addition to our itinerary.

We explored the area, laughed our way through the photos, and then continued our drive towards Milan, enjoying the beautiful scenery and reflecting on everything we had experienced over the previous days.

Day 6: Exploring Milan

For our final day, we stayed in Milan.

We left the car in a parking garage and used public transportation to explore the city centre. It made getting around much easier and saved us from dealing with Milan’s traffic.

The highlight of the day was undoubtedly the magnificent Duomo di Milano.

Seeing it in person is one of those moments that photos simply can’t prepare you for. No matter how many pictures you’ve seen online, it’s even more impressive in real life.

We spent the rest of the day wandering through the city, enjoying our final Italian meals, doing a little souvenir shopping, and making the most of our last few hours in Italy.

The following morning, we drove to Bergamo Airport and flew back home.

As always, before the trip had even officially ended, we were already talking about where our next girls’ trip would take us. Next station Lisbon.

Tips for Planning a Tuscany Road Trip

Here are a few things we learned during our trip that I think are worth keeping in mind if you’re planning a similar itinerary:

Rent a car. If you want to explore beyond Florence, having your own car gives you the freedom to discover Tuscany at your own pace.
Book accommodation with parking. Parking can be expensive and difficult to find, especially near historic city centres.
Avoid driving into historic centres. Many Italian cities have ZTL (Limited Traffic Zone) areas, and entering them without permission can result in hefty fines.
Stay at least two nights in Florence. This gives you enough time to explore the city without feeling rushed while still using it as a convenient base for day trips.

Driving in Italy

Driving through Tuscany was honestly one of the highlights of the trip.

Having the freedom to stop whenever we wanted, enjoy the scenery, and explore small villages made the experience even more memorable.That said, driving in Italy isn’t always as straightforward as you might expect.

Between ZTL zones, motorway tolls, parking rules, and some surprisingly expensive fines, we definitely learned a few lessons along the way.

Instead of making this article even longer, I put together a complete guide to driving in Italy, where I share everything we learned, including the mistakes to avoid before renting a car.

What We Loved Most

If I had to choose the highlights of this trip, Siena would probably be at the top of the list.

The city felt authentic, less crowded than Florence, and incredibly photogenic. Honestly, every street looked like a postcard.

San Gimignano was another favourite. We originally went there just to try the famous gelato from Gelateria Dondoli, but the town itself completely won us over. The medieval towers, charming little shops, and relaxed atmosphere made it one of the most memorable stops of the entire trip.

Of course, Florence deserves a mention too. The city is beautiful, vibrant, and full of history. Spending several days there allowed us to experience it at a slower pace instead of rushing from one attraction to the next.

Finally, one of the best parts of the trip was simply driving through Tuscany. The rolling hills, vineyards, tiny villages, and scenic roads often became attractions of their own. Some of our favourite moments weren’t planned at all, they happened somewhere between one destination and the next.

What We Would Do Differently

Looking back, there are a few things we would change if we did this road trip again.

First, we would probably spend less time in Florence and dedicate an extra day to exploring smaller Tuscan villages. Some of our favourite moments actually happened outside the major cities.

We would also make a few more unplanned countryside stops instead of focusing mostly on the larger towns. Tuscany is one of those places where the drive itself is just as beautiful as the destinations.

As for Milan, I’m still not entirely convinced that one day was enough. We managed to see the main highlights, but another night would have given us more time to explore the city without feeling rushed.

Finally, I would leave a little more room for spontaneity. Sometimes the best travel memories come from places you never planned to visit in the first place.

Would We Do This Road Trip Again?

Absolutely.

Tuscany is one of those destinations that feels impossible to fully explore in a single trip.

Even after six days, we left with a list of places we still wanted to visit.

The combination of historic cities, charming villages, incredible food, scenic drives, and the relaxed Italian lifestyle made this one of my favourite girls’ trips so far.

If you have around six days and are looking for a road trip that combines culture, amazing food, beautiful landscapes, and plenty of photo opportunities, I genuinely think this itinerary is a great place to start.

Would I go back?
Without a second thought.

Mostly for the gelato… but let’s just say it’s for the culture.

Is 6 Days Enough for Tuscany?

In our opinion, six days is enough to experience Tuscany’s highlights, especially if you’re travelling by car.

We managed to explore Florence, Siena, San Gimignano, Pisa, and several smaller stops while still having time to enjoy the journey itself.

That said, if you’d like to visit more villages, spend time at wineries, or simply slow down and enjoy the countryside, I would recommend staying for 8–10 days.

Final Thoughts

Tuscany surprised me more than I expected.

I thought I would remember the famous landmarks the most, but what has stayed with me are the quiet countryside roads, the small villages, the evening walks through Florence, and the simple moments shared with my friends.

That’s exactly the kind of trip I would happily do all over again.

Planning Your Own Tuscany Road Trip?

I hope this itinerary helps you plan your own adventure through Tuscany.

If you have any questions, feel free to leave a comment below. And if you’re looking for more inspiration, don’t forget to check out my other Italy travel guides.

I have plenty more coming soon!

The Ultimate 6-Day Tuscany Road Trip Itinerary: Florence, Siena, San Gimignano & Pisa