Traveling with a toddler can seem daunting at first, but let me assure you—it’s an adventure worth embarking on. Recently, my family and I decided to explore the beautiful country of Italy with our soon-to-be 2-year-old, and it turned out to be an incredibly rewarding experience. From bustling cities to serene lakeside towns, Italy offered something for every member of our family, including our little one. Be sure to make it to the very end for some family travel tips!
Milan
Our journey kicked off in Milan, where we enjoyed a three-night stay at the luxurious Excelsior Hotel Gallia. Situated right in the heart of the city, this hotel served as our perfect launching pad for immersing ourselves in Milan’s vibrant culture and attractions. Despite the city’s lively atmosphere, we discovered that Milan is incredibly family-friendly. We wasted no time marveling at the stunning Duomo di Milano, leisurely strolling through the iconic Galleria Vittorio Emanuele II, and treating ourselves to some delicious gelato along the way. And let’s not overlook the playgrounds—Milan’s parks provided an ideal spot for our little one to let loose and burn off some energy.
Now, let’s talk Duomo rooftop. We opted for the elevator entrance ticket because, let’s face it, lugging a stroller up all those stairs is a workout even for a seasoned gym-goer. Pro tip: leave the stroller behind and save yourself the hassle of collapsing and carrying it around. Trust me, those rooftop alcoves are a labyrinth of stairs—great for a cardio session, not so great for stroller maneuvers. And speaking of stairs, once we reached the other end of the rooftop, our tired legs yearned for a shortcut. Luckily, security officer nearby lead us to a hidden elevator exit.
In addition to our Duomo escapade, we treated ourselves to some high-end retail therapy at the Galleria, where even our little companion received the royal treatment. Refreshments were abundant, with water and “ACE” juice readily available at every turn. From there, we wandered through the city streets to Sforzesco Castle, our energy waning by the journey’s end. Opting for convenience, we hopped on the subway to reach the nearby station, eager to return to our hotel for some rest before dinner.
After our Duomo adventure, it was time for a snack. We walked back into the Galleria and made a beeline for Venchi Cioccolato e Gelato. A short wait for a table gave us ample time to admire the bustling scene below and strategize our next move over delectable sweets and, of course, gelato.
Before bidding farewell to Milan, we spent another day near the Duomo, watching our daughter delight in chasing pigeons amidst the pure opulence and grandeur of the surroundings. Although we had hoped to catch a glimpse of “The Last Supper” painting, we were disappointed to find tickets sold out. Lesson learned: book those tickets in advance if da Vinci’s masterpiece is at the top of your must-see list!
Lake Como
Next, we headed to Lecco for three nights, using it as a base for day trips to Varenna and Bellagio. The scenic beauty of Lake Como took our breath away, and our toddler was mesmerized by the shimmering waters, blooming flowers and quaint villages. Varenna and Bellagio were particularly charming, with their colorful buildings, cobbled streets, and panoramic views of the lake. We spent our days leisurely exploring and enjoying delicious meals overlooking the water.
Lecco
Lecco is a charming city that serves as an excellent base for exploring the Lake Como region. Slightly off the beaten path compared to the more popular towns of Como and Bellagio, Lecco offers a refreshing change of pace. Despite its tranquil ambiance, Lecco is bustling with local life, making it feel authentic and vibrant.
Situated on the shores of Lake Como, Lecco boasts a picturesque promenade that invites leisurely strolls and moments of relaxation by the water. While many tourists flock to restaurants with panoramic lake views or prime locations in the main squares, we discovered that some of the best culinary experiences in Lecco are found off the beaten path.
We found Lecco to be an ideal home base for our family adventures. With a grocery store conveniently located nearby, we stocked up on snacks like fresh fruit and cheese, perfect for impromptu picnics by the lake. Additionally, Lecco’s central location made it incredibly convenient for our day trips to Varenna and Bellagio, both just a short 30-minute drive away.
Embarking on separate day trips to Varenna and Bellagio allowed us to fully immerse ourselves in the charm and beauty of each destination without feeling rushed. And returning to the serene ambiance of Lecco at the end of each day was the perfect way to unwind and recharge for the next adventure.
Bellagio
During our excursion to Bellagio, we encountered the usual challenges that come with traveling with a toddler—some days are smoother than others. This particular day started a bit sluggishly, with the usual morning routine of breakfast and preparation taking longer than anticipated. Despite the city being only about 30 minutes away, the winding roads extended our travel time. By the time we reached Bellagio, it was nearing lunchtime, and finding parking proved to be a bit of a task. We eventually secured a spot at the top of the city, where one of the spots I had researched, La Terrazza Lake Como, had just opened its doors. We snagged a table on the terrace, offering breathtaking views of the lake and mountains, and treated ourselves to some delicious pasta.
With satisfied stomachs, we embarked on a leisurely stroll downhill towards the lake, making a mandatory pit stop for gelato along the way. Our walk took us all the way down to Punta Spartivento, where we marveled at the beauty of the lake and surrounding mountains. We meandered back through the city, exploring its charming narrow streets and watching the bustling ferry activity at the waterfront. Before heading back to the car, we let our little one burn off some energy at Parco Giochi, a delightful park nearby. Unfortunately, our return journey was marred by our daughter falling ill due to the winding roads, but she bounced back by the time we reached our hotel and was ready to venture out for dinner.
Varenna
On our final day before heading to Lake Maggiore, we explored the picturesque town of Varenna. Parking proved to be a challenge once again, so arriving early is advisable. Opting for a simple yet satisfying lunch of pizza slices in the town square shaded by trees, we soaked in the serene atmosphere. Post-lunch, we wandered through Villa Monastero, admiring its enchanting gardens and basking in the sunshine. Adjacent to Villa Monastero, we explored the centuries-old terraced gardens of Villa Cipressi, capturing precious family moments amidst the ancient cypress trees and stunning lake views.
After our garden escapades, we navigated the labyrinth of small streets back to the town center, passing by countless charming shops, cafes, and, of course, gelaterias. We couldn’t resist picking up a few souvenirs and enjoying more gelato by the water before bidding farewell to Varenna and embarking on the scenic drive back to Lecco.
Lake Majorie
Our journey continued to our final destination: Lake Maggiore, where we indulged in a three-night stay at the magnificent Grand Hotel Des Iles Borromées in the charming city of Stresa. The highlight of our time here undoubtedly revolved around our visit to Isola Bella, one of the Borromean Islands. Our toddler was captivated by the opulent palace and verdant gardens, while we savored leisurely strolls amidst the breathtaking scenery and relished in the lakeside playground.
Stresa
Stresa, Situated on Lake Maggiore, Italy’s second-largest lake, greeted us with panoramic vistas at every turn. A delightful promenade traced the coastline to the main town center, where we discovered charming restaurants for evening dining and a Carrefour for stocking up on snacks. A exciting find in Stresa was the lakeside playground, providing endless entertainment for our little one, despite the chilly May waters. The playground became a pre-dinner ritual, offering moments of joy and laughter against the picturesque backdrop of the lake.
Our second day in Stresa was filled with even more adventures as we embarked on a ferry journey to Isola Bella to explore the majestic Palazzo Borromeo. Convenient stroller storage at the palace eased our exploration of its stunning interiors and sprawling gardens. By the end of our visit, exhaustion had caught up with us, with our daughter nodding off in her stroller as we cruised back to the hotel.
We dedicated our last afternoon to relaxation, basking in the sunshine at the hotel pool before one final rendezvous at the lakeside playground. As evening descended, we decided to savor the culinary delights of Lo Stornello, a Michelin restaurant. The restaurant provided a wonderful dining experience, and the staff went above and beyond to accommodate us, especially considering we had a tired toddler nearing bedtime. Their kindness and understanding made our evening truly memorable. With satisfied bellies and fond memories, we returned to our hotel room to pack for our journey home the next day. Though bidding farewell to Italy was bittersweet, the memories we created will be cherished for years to come.
Overall Thoughts & Tips
Throughout our journey, we discovered that traveling with a child doesn’t have to be frightening. In fact, it can be incredibly rewarding. We didn’t have a complete plan of what we wanted to do each day, and that was okay. We embraced spontaneity and let ourselves be guided by our toddler’s interests and energy levels.
One thing we noticed was how much Italians love kids. Everywhere we went, we were greeted with smiles and warmth. Restaurants were incredibly accommodating, offering high chairs and children’s menus. And of course, there was pasta—our daughter’s favorite dish, which she happily devoured at every meal.
Though this marked our daughter’s third European adventure, Italy undoubtedly stands out as a top destination for families with young children. From dedicated family lines at airports and attractions to a plethora of outdoor activities, Italy offers endless opportunities for family fun. We discovered that the most precious moments often arose from the simplest experiences—strolling leisurely along the lakeshore, indulging in picnics amidst verdant parks, and relishing the sunset as a family.
While this marked my first time exploring Northern Italy, my wife and I had previously ventured to Italy twice before. Our past adventures took us to Rome, Florence, Venice, and a memorable trip to the Amalfi coast. Additionally, many years ago, I had the pleasure of skiing in Cortina, home to the 1956 Winter Olympics and the upcoming 2026 Winter Olympics..
Traveling to Italy with our toddler was an unforgettable experience that we’ll cherish forever. It taught us to embrace the unexpected, savor the little moments, and most importantly, to never underestimate the joy of exploring the world through a child’s eyes. So if you’re thinking about taking your little one on an adventure, don’t hesitate—Italy awaits, ready to enchant and inspire both young and old alike. Buon viaggio!
And remember, whether you’re planning your Italian adventure as a family, couple, or solo traveler, I’m here to turn your dreams into reality. Don’t hesitate to reach out to me at Luke@worldclasswonderers.com and let’s make it the trip of a lifetime together!