Italy Beyond the Obvious

Italy Beyond the Obvious started in August of 2008, when friends of friends told me they’d be happy to pay for a trip planning service. As soon as you work as a tour leader in Italy, everyone wants advice. So I’d been planning trips to Italy for friends and family since about the mid-1990′s , and until August of 2008 I wasn’t charging for them. But when I started spending time getting to know my travelers in order to make good recommendations, I realized that it was much more time-consuming compared to doing it for friends I already knew well. People said they’d be happy to pay for such a valuable service and thus Italy Beyond the Obvious was born. I have had more work than I can handle ever since.

From Owner Madeline Jhawar….

I grew up mainly in Edmonton, Canada, but spent about 5 years living in Italy.

I have also lived in Brussels, Stockholm, Milan, Vancouver, New York, Boston, Chicago, and San Francisco. (I define “lived” as having spent at least a year in the place.) I have a Linguistics degree from Queen’s University, Canada and spent 8 years at Arrow Electronics in international operations.  My husband is British-Indian and we have 2 kids (who describe themselves as “half British, half Indian, half Canadian and half American.”).

Italy and I go back a couple decades. I visited Italy for the first time as an exchange student for a year after high school. It was a tough year and it was a fantastic year. I learned to speak Italian so well that when I started University back in Canada, I finished all the Italian courses in my first year and then worked as an Italian teaching assistant at the University for the remaining 3 years of my degree.

Tour Guide in Italy

After graduation, I got a job with the hiking and biking company, Butterfield & Robinson, and led travelers on week-long biking and hiking tours in Tuscany, the Veneto, Parma, Italian Lakes, and the Cinque Terre. To them, my co-guide and I were the face of the company, their translators, van drivers, guides-on-a-bike, luggage haulers, and bike mechanics. I led wine tastings and castle tours and was, in general, problem-solver extraordinaire.

Expatriate Assignment in Milan

While biking in Tuscany, one of the B&R clients offered me a job in international operations at Arrow Electronics. I ended up working for her for over 8 years. After being trained in NY and doing an assignment in Stockholm, I moved back to Italy – to Milan this time. I found an apartment right near Piazza Duomo and worked as Southern European operations manager, for 2.5 years.

Founder of Italy Beyond the Obvious: 2008

After more than 15 years of helping family and friends create Italy vacations, in 2008 I gave some thought to my travel philosophy, my product, my business model, and my fees, and set up a website and business for Italy Beyond the Obvious.

Read our interview about experiential travel with TravelDew


About the Italy Beyond the Obvious Team

The beauty of Italy sells itself, but there is a lot of work involved in putting together an amazing trip! We have guides and drivers in Italy that make our trips amazing, but our team of trip planners make the magic happen, seamlessly and stress-free. Our team is completely remote, located across four different time zones. We use zoom and skype and slack and WhatsApp to communicate, and online planning tools to make sure that no detail falls through the cracks.

Claudia Marchesi, Milan

















Claudia helps with the behind-the-scenes planning and provides on-trip support. Originally from Milan, Claudia speaks perfect English and has a “how can I help you” customer service attitude. Platinum travelers sometimes meet Claudia: she’ll take them on a walking tour of Milan, act as an interpreter, or just be in touch via text, email, phone, or What’s App to help in any way that is needed.


Carolina Zuniga, Medellin

















Caro is the Project Manager at Italy Beyond the Obvious. She has a passion for travel and spent a year living in Italy learning Italian while being an AuPair. She is currently based in Colombia but daydreams about her time in Rome on a daily basis. She loves calendar, budgets, animals and dancing.


Francesca Terraccia, London

















Originally from Milan, Francesca moved to London with her husband and two teenagers several years ago. With a Ph.D in history and a specialization in women in the Italian church, Francesca is not only a great trip planner, but is a wizard at finding genealogical information buried in church documents!