Our recent trip to Italy was nothing short of a dream come true. From the ancient ruins of Rome to the rolling vineyards of Tuscany, every moment was filled with wonder, learning, and just the right amount of flexibility—a newfound travel trait I didn’t realize I had until this trip! Traveling with a young child can sometimes mean letting go of the rules, and this adventure taught me that a little flexibility can go a long way in making the experience truly magical.
Annabelle, our little explorer, was absolutely thrilled by Gladiator School in Rome. Imagine her wide-eyed excitement as she donned armor and learned the ancient techniques of battle. It was an immersive history lesson turned thrilling adventure, and she cherished every moment. It was a reminder of how hands-on activities like these can make history come alive for children.
One of the biggest lessons learned on this trip was the importance of incorporating downtime into our itinerary. With so much to see and do, it’s tempting to pack the days full, but having some free time to relax by the pool at our hotel or simply wander through the streets made a world of difference. In fact, staying at a hotel with a pool, which I used to dismiss as unnecessary, proved to be a brilliant choice. Annabelle loved it, and it became our go-to reward after long days of exploration.
We spent a relaxing day at the Castel Monastero Resort & Spa in Tuscany, nestled in the serene countryside. The former medieval village turned luxury resort was the perfect place to unwind after our flight, setting the tone for the rest of our adventure.
Cooking classes are always a hit with my travelers, and our time in Italy was no exception. The whole family enjoyed getting hands-on with authentic Italian cuisine during our cooking class in Florence. We started early, meeting our guide at the Grand Hotel Minerva, and walked to the Towns of Italy Cooking School. Here, we explored local markets, selecting fresh ingredients, and then learned how to make homemade pasta under the guidance of a Tuscan chef. It was a delightful way to connect with the culture beyond just dining out.
Speaking of dining, Maito and Alfredo were our favorite meals during the trip, though we often found ourselves at more touristy spots that opened early due to Annabelle’s bedtime. However, we learned to be flexible with the rules—bedtime included—because, after all, when in Rome (or anywhere in Italy), you can have gelato for dinner!
Florence was a treasure trove of art, history, and culture. We started our day with a drive from Tuscany, arriving at the Grand Hotel Minerva, a hotel rich in history dating back to 1850. Despite the Bank Holiday festivities along the riverbanks, we managed to explore the city’s iconic sites, including the Cattedrale di Santa Maria del Fiore, the Uffizi Gallery, and the Galleria dell’Accademia, home to Michelangelo’s David. The day ended with a breathtaking view of Florence from La Loggia, where we enjoyed a family dinner at the top of Piazzale Michelangelo.
One of the highlights of our trip was our full-day tour of Siena and the Brunello di Montalcino region. The rolling hills, the rich history, and of course, the wine were spectacular. My dad declared the Chef’s tasting menu at Contrada at Hotel Monastero one of the best meals he’s ever had—a high compliment from a seasoned traveler!
One of the most memorable keepsakes from our trip was our Flytographer session at the Trevi Fountain. The early morning photoshoot not only helped us avoid the crowds but also captured our family against the stunning backdrop of one of Rome’s most iconic landmarks. These photos are more than just pictures; they’re memories we’ll cherish forever.
Guides are worth their weight in gold, especially when traveling with children. Our guide, Samantha, in Cinque Terre, was absolutely fantastic. She brought the history and culture of the area to life in a way that kept Annabelle engaged and eager to learn more. It’s these personal connections and knowledgeable insights that transform a good trip into an unforgettable one.
Traveling with extended family can be incredibly rewarding. We were fortunate to have Annabelle’s grandparents join us for part of the trip, and it added a special layer of joy to our journey. Having extra hands and different perspectives enriched our experience and created memories that will last a lifetime.
Though I wouldn’t usually describe myself as a flexible person, this trip reminded me of the importance of being adaptable, especially when traveling with kids. From bringing our own car seats to being prepared with exciting activities like a puzzle book for the Colosseum and Uffizi, we learned to roll with the punches and make the most of every moment. While everyone says you don’t need a lot of time in Rome, I found myself wishing we had more. We tried to save a little by booking a non-private tour at the Vatican, but if we could do it again, I’d definitely invest in a private guide to avoid the overwhelming crowds.
Our trip to Italy was everything I hoped it would be and more. It was a learning experience, not just in terms of history and culture, but in understanding how to make family travel work for us. Flexibility, a bit of planning, and a willingness to embrace the unexpected were key. Whether it was the joy of watching Annabelle learn to wield a sword like a gladiator, the peace of a quiet moment by the pool, or the delight of savoring fresh pasta together, every part of our journey contributed to an unforgettable adventure.
Italy has a way of leaving its mark on your heart, and I know this trip will be one we talk about for years to come. And as for me, I’ve realized that rules are meant to be bent—at least when you’re on vacation!ily through these historic wonders, creating memories that will both educate and enchant.
Meet Christina Vieira, a Traveler, a Planner, and a Mom. She is also the owner of Showcase the World Travel, a modern travel agency that helps busy Moms take the vacation they deserve without adding “planning it all” to their to-do lists. After all, Mom should get to enjoy their vacation too.
She specializes in Disney, Caribbean, Europe and has helped dozens of families have magical vacations that they will always remember. She loves traveling with her four-year-old daughter, Annabelle. Her favorite destinations include Walt Disney World, Wyoming, and Prague.
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