Italy with Kids: Tips and Advice from the Family Travel Expert and Prontopia Founder Shannon Kenny

Traveling with kids is truly fun and rewarding for parents. It does not only give opportunities for endless bonding. It also gives way to learning. In Italy, there are a ton of museums, chapels, zoos, and other places that are great for children. Add the ancient ruins, parks, spooky places, and castles – there are bits and pieces of history that are worth exploring with your young travel companions.

But traveling with kids comes with some challenges too. While you are all excited to roam around and explore the best of the country, the fact remains that you are visiting strange places and most of the time, you will find yourself clueless about what to expect, where to go, where to stay, etc. Even the most basic things like prepping up for a tour, finding a place to eat, booking an appointment at a museum can all be daunting.

So, we asked Shannon Kenny, a travel expert and Founder & CEO of Prontopia, to give us some great tips to make family travels in Italy more fun and less stressful.

For you, what's the best thing about traveling?

“Human connection, of course! And deepening my own self-knowledge by understanding the diversity of the human condition, in the context of our common humanity on this planet.

To me, that is the most beautiful thing about traveling, and this also crosses time and space. If I am standing in front of a work of art (such as Michelangelo’s Pieta), or natural monument (such as Grand Canyon), such aesthetic experiences make me feel at the same time a deep sense of personal awareness of who I am, relative to the awe of beauty and emotion that such sites have inspired for so many others. Traveling makes me feel connected.”

What makes Italy a top family travel destination?

“The Italian culture, in general, is very kid-friendly, and so kids are welcomed almost everywhere. Secondly, the history, nature, and food in Italy all offer something for everyone, of all ages.”

How did you arrive at the idea of creating an app like Prontopia? What was your inspiration?

“During my 15 years as an entrepreneur in travel, I experienced the ripple effects of infamous disruptions in the industry, such as the rise of Airbnb and the use of smartphones. While these shifts have opened up many opportunities, they have also left gaps.  

Information is more widely available than ever, online or in-app but often you just need a real live person. While operating my previous companies and during my own travel as a solo female and as a mom traveling alone with young children, I increasingly observed how the rise of Airbnb and a DIY travel mentality have left a false sense that it is easy to find what you need once you arrive.

In reality, the customer experience today tells a different story as travelers face unforeseen challenges in foreign, walkable city centers getting where they need to go easily, and finding necessities.”

How did Prontopia start? What makes it different from other mobile travel solutions?

“Prontopia is a California travel tech company that launched in Venice in May 2018, and expanded to Florence and Rome later that year, in October 2018.

We provide immediate in-person help in the city when and where you need it, versus other digital solutions that just provide information. Other differentiators include:

What are the top 5 tips you can give for family travelers?

1. Involve your children in the trip planning process so that they have buy-in and high-level interest. Read books and view historical and cultural videos on YouTube together, and discuss which sites or experiences interest your child and why. Then be sure to incorporate some of your child’s choices into your final itinerary.
2.  Stay at least 3 nights in each place to minimize stressful transitions. Plan your itinerary around central locations that allow you to do day trips to the main sites you want to see, rather than changing locations more frequently than 3 nights. This will save you time and money, and minimize the errors that can often occur when transferring from one location to another while traveling in an unfamiliar country.
3. Whereas getting lost and wandering amid medieval streets is romantic for couples, young children tend to give excessive and random walking around two thumbs down! Without a firm plan to get where you need to go easily by foot in Italy’s carless city centers, you are likely to hear the equivalent of the familiar refrain “are we there yet”? Using Prontopia to connect with a friendly local in the city for help getting easily where you need to go will also reduce the stress of getting lost when you are en route to tours, activities, or meals that the kids are excited about. It also gives the whole family a chance to feel connected to the city by learning about it along the way from a locals’ viewpoint. This appeals to kids’ natural curiosity and exposes them to meaningful difference and cultural understanding.
4. Embrace slow travel, and do not over schedule your itinerary. It is easy to fall into the trap of trying to check many things off a list that you want to do or see as a family when visiting Italy. But packing too much can also mean the kids become overtired or overwhelmed, and do not, in the end, experience the full benefits of what parents intended. Plan a reasonable pace for your itinerary, that gives you time for surprising or serendipitous discoveries, and most of all, time for calm and mindful periods together as a family. Magic memories often happen in the in-between and un-scheduled times while traveling.
5. Pack light! Regardless of what type of itinerary you have, traveling in Italy will require navigating sections of walking or getting on and off trains in which excessive luggage would be difficult, if not impossible, to manage. Resist the temptation to overpack and stick to a strict packing list of just the necessities. Laundry facilities (especially the Fluff and Fold type) are easy to find in Italy’s city centers and are not expensive, and if you are staying in a vacation rental, chances are you will have a washing machine (but no dryer!).

More about Prontopia Founder Shannon Kenny

Shannon holds a Master's Degree in Medieval and Renaissance History. She worked as a published author, editor, and educator in the fields of history, French and Italian language, the social sciences, and educational and boutique travel for over 17 years. After many years of traveling to Italy for both work and pleasure, she founded the international children’s cultural program Arte al Sole in 2007 to serve the needs of families traveling and living abroad. To meet families’ demand for quality and trustworthy travel information, in 2008 she launched Italiakids.com, an online resource for family travel to Italy.  

As Italiakids.com grew, readers increasingly reached out to our company with requests for travel concierge trip planning for itineraries that included Italy as well as other destinations in Europe. Due to word-of-mouth referrals among this clientele, Shannon and her team expanded that company by request beyond family travel to design all manner of itineraries, and Elaia Travel was born. Her travel and lifestyle digital content company, ViaPapera also produced the popular Italy travel tip YouTube series, Uno Minuto with Shannon Kenny.

In 2017, she founded Prontopia, an app that gives travelers a way to request on-demand in-person help from locals with common everyday traveler problems, to make trips stress free and full of meaningful connections.