We started working together in 2018. Kara was working as an independent agent back then and was looking for a company that knew Italy well enough to customize a large destination wedding and fate brought her to the company Claire was working for in Rome. It would be another year before we finally met on a train to Naples.
From sofas on opposite sides of the world, we spent lockdown planning to start a company together (as well as several road trips!) when travel became possible again.
It was easier in our dreams than in reality and life took us in other directions for a bit while tourism recovered. But after planning a vacation to give Kara’s family an authentic experience of central Italy while avoiding crushing crowds, we knew the moment had come.
We took all our experience of living and working in Italy, of travel and traveling, and of knowing how great together is and set up My Italy Itinerary one rainy (in Rome)/snowy (in Indiana) day.
and our favorite itineraries
I grew up in Northern NY state in the Thousand Islands very near to the Canadian border. I mostly traveled throughout the US and Canada as a child but was able to travel to England and France with a high school French class. From that point on, I knew that I needed more!
I was lucky to have the opportunity to move to Italy while in my 20s and spent over 3 years traveling throughout all of Italy and Europe. Every time I go back to Italy, I discover something new. My perfect itinerary changes with every visit. I love Northern Italy and the Dolomites. I adore Venice especially in the colder months after it rains and a fog hangs over the canals. It is hauntingly beautiful and romantic. One tip that I will give if you go to Venice during peak season- wake up very early in the morning and explore before everyone else is awake.
Naples is another city that I love. The food is amazing and the underground tour is a must. I feel like I’ve gone back in time when I visit Naples. It’s almost like I can hear Dean Martin singing “That’s Amore” as I drink wine and eat the best pizza in the world (sorry, Rome).
I dreamed of living in Rome ever since I decided to study ancient history at university. Back then, my favorite Italy itinerary -Rome, Naples, Vesuvius and Paestum- was all about being immersed in the classical world and eating lots of delicious vegetarian-friendly food.
Since moving to Rome, Naples has become an easy day trip any time I want pizza, and I prefer to head north for longer trips. I love Turin, surrounded by the Alps, Milan which everyone knows for fashion but I visit for the museums, and Venice, but only in winter when there are no crowds and the weather is dramatic and unpredictable.
I'm still amazed at the diversity of history, food and traditions in each region. I have such respect for everyone fighting to keep those differences alive in the face of mass tourism. Supporting ethical, local businesses is extremely important to us and we believe that the chance to meet locals and see Italy in her unfiltered complexity gives you a unique, meaningful experience that will stay with you, and one that you could never have on a cruise or as part of a tour group.
We put everything we’ve learned living and travelling in Italy into our itineraries. Working with us you instantly gain access to a wealth of experience and knowledge, along with these fundamental beliefs of how to keep travel enjoyable in a crazy world.
People make a place authentic. Every region of Italy has its own culture, food and history that you’ll only discover when you get in touch with locals. This isn’t hard to do. Stay in a hotel that employs locals, take tours with people from the place you want to discover, avoid chain restaurants and buy locally produced souvenirs.
There’s more to Italy than Instagrammable moments and there are plenty of ways for tourists to be a positive force. Visit one place you’ve never heard of, take a regional train somewhere that doesn’t see many tourists, stay longer in a single place. You’ll support the local economy and touch the real Italy.
We love spontaneity, but not when it comes to vacation planning. Making the most of your time in Italy and seeing the places that matter to you most requires serious research and careful planning. Find out what has to be booked in advance, the best days to visit particular towns and how long you should stay in a destination
Cram as many activities as humanly possible in a week or carefully pick and choose the places you visit? Our advice? Plan your vacation like you’re going to come back to Italy again. Enjoy seeing a few places really well and experiencing the Italian pace of life and trust that you will be able to come back and do the same in another part of Italy next time.