PETROGNANO, TUSCANY— It all starts with a lady named Annagloria. In 2009 I started planning a long trip that would take my family through 17 countries and 72 cities on two continents. We left the United States in August 2011, but a trip such as that takes a lot of planning.
For the two years prior, I spent most nights from 10 PM until midnight with my laptop researching destinations, restaurants to visit, villas and apartments to rent, and things to do and see. I set up a folder for each country, and within that country, I set up subfolders related to cities and regions. My Italy folder included Venice, Milan, Bologna, Rome, Ostuni, Sicily— along with several cities within that island— and of course, Tuscany. I probably spent the most time researching Tuscany because we would be there the longest.
I kept coming back to one particular Villa in the Tuscan countryside. It was a 1000-year old tower and a 1000-year old barn that had been completely renovated that year. The lady who owned the Villa that I was communicating with spoke English well, seemed to be a foodie, and really “got” what my family and I were doing. So I booked her place, Villa Il Santo.
The Villa, the adjoining two towns, and the family who owned the Villa were the perfect choices. The Villa lies at the end of a remote gravel road in the Tuscan countryside; nothing around but a 30-mile view to the west of grapes and olives. No tourists hang out in the town or at the restaurants. It’s all locals. Exactly what I was looking for, but the bonus was that within 30 minutes, we could be in the city center of either Florence or Siena. It was the best of both worlds; perfect.
Though the bonus was Annagloria, her husband Enzo, and their family, they were the perfect hosts and helped guide us through those early days in Tuscany when I was just learning the ropes. Later, when I started hosting tours in this part of the world, Annagloria and her family became vital components in the process. She introduced me to a guide for Siena and Florence named Marina Mengelberg. She is Dutch but has lived in Tuscany for the past 20 years. She also introduced me to Ricardo, another guide we use in Florence. In turn, Marina introduced me to Jesse, who helps with our tours in Rome and Amalfi and just spent ten days with us helping lead my tour through Spain.
All of these people have introduced us to other people and other places. I tell the guests I host on these tours that one of the great surprises leading people through Tuscany, Northern Italy, or Southern Italy— or Spain, for that matter— that I knew I would have fun doing it. Still, I never knew I would make such good friendships with the people who travel with me. That has been the case, but also, it’s the same with the original trip; I knew I would have fun traveling with my family for six months traversing Europe. But I never knew I would make lifetime friends overseas in the process.
The key to my business success over the years (to the extent that I have had any business success over the years) is that I have surrounded myself with more talented people than myself. If I’m good at anything in business, it’s picking talented people and surrounding myself with them. I choose the path, point the ship in the right direction, and get out of the way so that those people can use their talents to help us reach the destination. The same goes for international travel. I am blessed that I have surrounded myself with talented people who help put these trips together and create once-in-a-lifetime experiences for Americans who travel to Europe.
It’s a career I never chose and almost fell backwards into. I never intended to be a host for European travel. I planned on doing this once and then moving on. But that first group had a waiting list, and then the waiting list grew a waiting list, and then the first people we took to Tuscany asked, “Where are we going next?“ And so we hit Northern Italy a few times. And then people asked, “Where are we going next?“ And so we hit Southern Italy with a few groups. A few weeks ago, when we finished traversing Spain from the north to the south, we had people on their fourth or fifth journey with me.
That is special. But I hesitate to take any credit for it because of the wonderful people I have met through the years, those who work with me, and those with whom I have surrounded myself. They are hard-working, talented, and extraordinary people who know the area and love hosting Americans.
Annagloria and Enzo know how to host Americans in their villas. Their children work hard to make guests happy and comfortable. Enzo has lived in the area his entire life, and Annagloria grew up in Florence, so they know the area well, which was huge on my initial visits. Marina is a licensed tour guide who has undergone a lot of intense studying and training in Florence and Siena. Ricardo grew up in Florence, and he knows the city well, as does his American-born wife, Cynthia.
There are countless restaurant and shop owners that we have come to know and love over the years to the point that when we arrive here, it feels like we’ve come home in a way. That doesn’t just happen without special places and special people. I am grateful for each and every one of them.