Italy with kids in the peak of summer during a jubilee year? What sounded like a recipe for disaster instead turned out to be the adventure of a lifetime. The trip started as just the four of us exploring Florence, Tuscany, Cinque Terre and Bologna, then expanded into a full-blown family reunion in Rome with my parents, brother, and his crew. What followed was 2+ weeks of Renaissance art, Tuscan vineyards, colorful Oceanside hill towns, Bolognese culinary delights, ancient Roman ruins, and more gelato than we could ever imagine. Here are the top 10 highlights from our Italian summer travels:

1. Walking through Florence’s art, architecture, and history
2. Making pasta from scratch near the Duomo
3. Spending a day wine tasting in the Tuscan countryside
4. Exploring Cinque Terre’s cliffside villages and coastal views
5. Eating our way through Bologna
6. Visiting the Ferrari museums in Modena
7. Taking the perfect day trip to San Marino
8. Seeing Rome’s ancient landmarks by golf cart
9. Visiting Vatican City’s museums, basilica, and papal audience
10. Indulging in a lotta Gelato

1. Walking through Florence’s art, architecture, and history

Florence was the first stop on our Italian adventures – a compact living museum of Renaissance art and architecture. Our AirBnB was right along the Arno River by the Ponte Vecchio, the old bridge still lined with jewelry shops. The covered walkway above was built by the Medici to connect the Uffizi to their residence.

We started where everyone does – Michelangelo’s David at the Galleria dell’Accademia – a massive statue hewn by the famed artist from a single piece of marble in 1504. Standing beneath the deceptively large sculpture, we were amazed by the lifelike minute details of every muscle and vein captured in stone. We also wandered through Piazza della Signoria, an open-air museum lined with statues including a replica of David, Neptune’s fountain, and Cellini’s bronze Perseus.

Of all the architectural wonders in Florence, The Duomo designed by Brunelleschi dominates the skyline with one of the largest masonry domes in the world. The frescoes covering the dome’s ceiling are stunning – it was hard to fathom how artists created such intricate work at those heights with only medieval tools. Our other highlights included catching sunset views of the city and Duomo from Piazzale Michelangelo, and a peaceful sunset cruise along the Arno watching the monuments bathed in the soft dusk light.

2. Making pasta from scratch near the Duomo

We traded sightseeing for pasta making one day, in a small underground room beneath the Brunelleschi restaurant, just steps from the Duomo. Chef Niccolò began with the basics — flour, eggs, and a drizzle of oil. The kiddos quickly hit it off with him, gathering around the table with quiet focus and eagerly volunteering for demonstrations, while the free-flowing wine kept Shelly and me in good spirits.

We started by making the dough, then shaped it into slightly misshapen ravioli, tagliatelle, and tortellini as Chef Niccolò got a bolognese going. The meal tasted even better since it was our own hand made creation. The whole experience was relaxed and casual — a simple, satisfying way to savor a slow-cooked, authentic Italian meal.

3. Spending a day wine tasting in the Tuscan countryside

During our Florence stay, we rented a car and drove south for a tour of the Chianti wine region in Tuscany. We followed narrow, winding roads past vineyards, stone farmhouses, and rows of cypress trees. The slow and scenic nature of our morning drive set the tone for the day. Our first stop was Santo Stefano, a small, family-run winery where we experienced an intimate private tasting with the owner. She poured us some tasty Chiantis, then gave us a tour of the property. The kiddos found the resident winery cat and that thankfully kept them occupied while we continued the tastings.

From there, we continued through the rolling Tuscan countryside to Castello di Verrazzano, a winery set inside a 15th century medieval castle overlooking the hills. The winery is named after Giovanni da Verrazzano, the first European explorer to explore the east coast of America on a voyage in 1524. We began with a short tour of the castles, where the kiddos found the customary feline resident, then stepped into the cool stone cellars. Next on the agenda was the main event – a lengthy and indulgent seven-course lunch paired with estate wines, served in a cozy tasting room with wide views of the surrounding vineyards. Well fed and unhurried, we drove back toward Florence, even stopping briefly in Siena before ending a satisfying day.

4. Exploring Cinque Terre’s cliffside villages and coastal views

Cinque Terre – meaning “five lands” in Italian – is a series of five scenic villages perched on steep cliffs along the Mediterranean coast. Pastel colored houses cling to the hillsides above turquoise waters, with green vineyards braiding the hilltops. This is the birthplace of pesto, famous throughout Italy for its fried anchovies, and home to excellent white wines.

We explored all five towns using the Cinque Terre pass for unlimited train rides between villages. Of the five, Monterosso had the best family beach, with wide shallow waters perfect for cooling off in the blazing August heat. Our grand finale was watching the spectacular sunset over the Mediterranean from our Airbnb terrace in Riomaggiore – witnessing the sun’s soft rays light up the pastel houses in ethereal shades as it dipped below the horizon.

5. Eating our way through Bologna

Bologna sits in the heart of Emilia-Romagna, widely considered the culinary center of Italy. The region is known for producing some of the country’s most celebrated foods: prosciutto and mortadella, fresh pastas like tortellini and lasagna, Parmigiano-Reggiano, and traditional balsamic vinegar. Bologna itself is best known for its namesake sauce, ragù alla bolognese. Of all the places we visited in Italy, it felt the least touristy, with a more local, day-to-day rhythm. Of all the places we visited in Italy, Bologna felt the least touristy, with a more local, everyday rhythm. Rather than famous landmarks, the city’s reputation comes from its food.

A few highlights of the meals we dug into in Bologna were the generous charcuterie spread at Simoni, a long-standing Bologna culinary institution, and hearty tagliatelle al ragù at Osteria dell’Orsa

6. Visiting the Ferrari museums in Modena

A short train ride from Bologna took us to Maranello, the heart of Ferrari, where all their Formula 1 cars are designed and built. Walking through the Museo Ferrari Maranello felt like a journey through automotive history – from Enzo’s earliest creations in the 1940s to the latest 2025 models fresh off the factory floors. After watching Michael Schumacher dominate F1 in that distinctive Ferrari red livery for years, it was surreal to actually be in Maranello. The kids were equally fascinated seeing the designs evolve over the decades, and couldn’t get enough of posing next to all the “cool red race cars.”

The Hall of Champions was packed with trophies from decades of F1 dominance, with Schumacher’s victories leading the way. Everywhere we looked there was red – the iconic ‘Cavellino’ prancing horse and Scuderia Ferrari logo marking Enzo’s lasting legacy throughout the museum. There’s also the Enzo Ferrari Museum in Modena focusing on the man himself, though we didn’t make it there this trip. By the end of our visit, we were all still buzzing about the speed and history on display.

7. Taking the perfect day trip to San Marino

While in Bologna, we took a day trip to San Marino, the world’s oldest sovereign republic, entirely surrounded by Italy. Visiting San Marino felt like stepping into a fairytale, with breathtaking castles perched high on Monte Titano. We wandered cobbled streets, explored the medieval Three Towers, climbed to the top for stunning views, and visited the basilica and parliament. We capped our San Marino adventure with an amazing meal that rivaled anything we’d had in Italy so far.

8. Seeing Rome’s ancient landmarks by golf cart

Rome was our final stop for a week long family reunion with my parents, brother, and his crew. We began our explorations of the ancient city of seven hills with a golf cart tour to get oriented around the main sights. In a single afternoon, we covered Piazza Navona, the Pantheon, Trevi Fountain, the Colosseum, Palatine Hill, and Circus Maximus. With blazing August heat and kids in tow, starting by golf cart was definitely the right call!

The next day we embarked on a guided tour of the Roman Forum and Colosseum on foot. Among the still standing stone monuments of the Forum, we wandered past the Temple of Saturn, stood in the ancient Senate House where Rome’s republic was born, and explored the House of the Vestal Virgins where sacred flames once burned for centuries. The Colosseum tour brought it all to life – the kids were mesmerized during the arena visit, imagining 50,000 roaring Romans as gladiators fought to their ghastly end.

We then wrapped up our Roman holiday one morning with photographer Roberta capturing memorable photos at these ancient landmarks – a perfect way to freeze our Roman adventure in time.

9. Visiting Vatican City’s museums, basilica, and papal audience

While in Rome, we carved out a full day to explore Vatican City, another sovereign state that is fully enclosed within Italy. Despite being the world’s smallest nation – the Vatican is yet home to one of the most expansive collections of art and history in Europe. We spent hours wandering the galleries of Vatican Museums, marveling at centuries of masterpieces, and took our time in the Sistine Chapel and St Peter’s Basilica. The following morning, we returned to St. Peter’s Square for the papal audience – an unforgettable moment seeing our very own ‘Chicago’ Pope in person.

10. Indulging in a lotta Gelato

Gelato was our constant indulgence in every city we visited – a daily ritual that was the perfect relief from the sweltering Italian summer heat. All over Italy each scoop we tasted was creamy, refreshing, and bursting with natural flavors – unlike anything from back home. The kiddos especially couldn’t get enough, and we still have fond memories our daily gelato breaks.

 

Italy delivered everything we had hoped for – the art lived up to the hype, the history immersive, the food was amazing, and the kids surprised us by actually paying attention in the museums. But the best part was having three generations together – fulfilling my parent’s long held desire to see the eternal city and Vatican together as a family. Arrivederci, Italia – we’ll be back!