One of the greatest benefits of living in Germany is the drive-ability to some of the world’s most beautiful places. This Summer, we decided to take advantage of our unique location, pack up the car, and head south to Tuscany. Since traveling with little ones can throw a kink into plans for a long road-trip, we decided to break up the long stretches and stay overnight in fun cities along the way. What started out as a Tuscan vacation turned into an Italian road-trip adventure, and I’m sharing our itinerary and stops we enjoyed (and wished we could have seen!) along the way.

Stuttgart to Milan

Milan is just about the halfway point between Stuttgart and Tuscany (more specifically, San Gimangio where we stayed during our trip). Although we had planned to arrive in Milan early afternoon and enjoy our first stop for an extended day trip, traffic had other plans and we ended up arriving at almost 8PM. *Now imagine two parents, and two children, driving for 9.5 hours when we’d planned on 5…*

Nonetheless, traffic and ornery babies definitely lend themselves to more frequent stops to stretch and shake out the crazies. Just past Zurich, there is a roadside stop with the most amazing view of a crystal blue lake surrounded by towering Swiss Alps. We discovered this stop en route to Lake Maggiore for our babymoon before Olivia was born, and I was happy to find out it was along the same route this time around. As a bonus, this road side heavenly view also has restrooms and benches wide enough for baby changes, so everyone can freshen up!

Related Post: Family Friendly Tuscany

Milan

So maybe we weren’t our best selves upon arrival, but I wanted to make the most of it and explore this Northern Italian city. With only 18 hours (including sleep time!) to spend, we experienced a crash course and dropped our bags at our apartment (more on this later!) and headed to the Arco Della Pace. From New York City to Paris, I love a good arc, and this one did not disappoint. We grabbed a few beers from a park vendor and watched Olivia run and play in the open space in front of the structure.

Arco Della Pace

Once we figured she had blown off enough steam to sit through dinner, we headed to Corso Sempione (the street opposite Piazza Sempione where the Arc is built). Restaurants with outdoor seating line this street, and there are so many options to choose from. We really liked the hustle and bustle of the street and felt relaxed dining with the girls here, not having to worry that they would be fussy. We chose dinner at Pizza Ok (and true to it’s name, the pizza was just OK.) Nonetheless, it did the trick and provided a stress free meal-something that cannot be taken for granted when traveling with toddlers!

Another must-see Milan stop is a great two-for as they’re both within eye shot of each other! The Duomo di Milano is an absolutely spectacular piece of architecture that is now seated among the most amazing I’ve ever seen. This Milan Cathedral took nearly six centuries to complete, and is the largest church in Italy, the third largest in Europe and the fourth largest in the world. [source] We were not prepared for the beautiful detail and craftsmanship of this cathedral, and I highly recommend a stop here while in Milan. If you’re looking to pop by avoiding crowds, I recommend before 8AM when it opens to visitors, as this is a hot tourist spot.

Duomo di Milano

While you’re in the area, hop over to Italy’s oldest active shopping mall, the Galleria Vittorio Emanuele II, designed in 1861. Certainly the most beautiful shopping mall I’ve ever seen (and a great spot if you’ve been saving your coins to buy a designer souvenir!)

Galleria Vittorio Emanuele II

To Stay:

We chose to stay in an Airbnb during our stay in Milan, and I cannot say enough good things about this apartment! The gated and private (and free!) parking directly next to the apartment was SO convenient, the elevator fit our double Bob stroller, it had Air Conditioning (which is a rare gem in European flats!), and the host was absolutely wonderful with local info and communication. I loved that we had two full bedrooms and bathrooms on two floors, and since I made sure to pack both girls’ sound machines, everyone got a wonderful night’s sleep (mostly me, because I drove the entire way and the bed was SUPER comfy!). The location was amazing and perfectly walkable, and I would absolutely stay here again on another visit to Milan.

Also Recommended:

2BR/2BA Apartment, Parking + Top Rated by Families!

2BR/2BA Apartment, Elevator + Top Rated by Families!

Whether you prefer apartments, hotels, or B&B’s always check out Booking.com for the most comprehensive list of available accommodations at your destination! Get $15 off your next booking (anywhere in the world!) HERE

More to See:

Starbucks Reserve Roastery // If you’re a coffee nut be sure to check out the Starbucks Reserve Roastery here in Milan. Completely unlike your neighborhood coffee shop, here you can admire the craftsmanship of coffee or even a cocktail at the Aperitivo bar!

“Milan is the third Starbucks Reserve Roastery in the world (the Seattle Roastery opened in 2014, and Shanghai in 2017) but the first where customers can move all the way around the bright green Scolari roaster (made in Italy, by the way) and watch every step of the coffee roasting process from bean to cup. ”

10 Things to Know About The Milan Roastery

Tuscany

Although the weather could have been better for our time in Tuscany, the ambiance, the wine, and the time with family was spectacular. Read about our experience HERE.

Related Post: Family Friendly Tuscany

Pisa

Our first stop on the way back from Tuscany was to visit the Leaning Tower of Pisa. Tyler and I were both impressed as to just how much the tower is actually leaning! There is no charge for admission to the park, and Pisa has many restaurants near the tower, so this is a great 1 hour or so pop-over (or more if you want to catch lunch!). Middle School Alex would have totally geeked out over getting to see this 😊

Cinque Terre

Our next stop was about a 2 hour drive from Pisa, Riomaggiore -one of the 5 towns that make up Cinque Terre. Tyler had included Cinque Terre on his bucket list years ago, and I wanted to surprise him for his birthday by rerouting us through at least one of the towns on our way home. I had considered an overnight here, or even a few days in one town, but after reading some reviews of the hike with kids, and the hotel arrangements, it didn’t seem like it would be a good fit to include as a bigger part of our trip. With that being said, the drive up the mountain was gorgeous, the city was adorable, parking was easy (in a structure on the outskirts of Riomaggiore, as they don’t allow traffic), and the scenery was gorgeous. The contrast from rolling hills, vineyards, and walled cities, to a sea breezy village was so lovely. I am SO glad we made this part of our route, and Tyler and I both agreed it was a great “fact finding mission” for a future trip of just the two of us to hike the trail.

Lake Como

The last stop (and overnight) on our roadtrip, was the northern Italian lake town of Como. In my world, Lake Como is synonymous with George Clooney’s Italian oasis, and it’s where my girl Chrissy Teigen *obsessed* and John Legend got married. When I was researching accommodations for the area, it made the most sense to stay in Como rather than one of the other lake towns (like Bellagio), only because Como was almost exactly on our existing route home. This way, we’d get to see the sights and also not steer too far off course (as Como is still about 4 hours or so from home).

We hit the jackpot again with our apartment, having an amazing location in town and only a 10 minute or so walk from the lake. Just around the corner from the cathedral, there were plenty of things to see, places to shop ($$$), and cafes to enjoy some good old fashioned people watching. We had an amazing dinner (pizza and wine, of course #dietstartstomorrow) and enjoyed a quick, but fun preview of Como. Another successful fact finding trip, to plan for future mom and dad only travels 😉

To Stay:

2 Bedroom, 1 Bathroom Como Apartment

Also recommended:

2 Bedroom Apartment with Lake View

To Eat:

Napule E’ Lago