Cultural Italy Blog: Art, Coffee & Love

Meet Our Travel Designers: Roberta Riddle


Roberta Riddle

I was born and raised in Milan, in the north in Lombardy. I started studying foreign languages and came to the United States to San Diego, CA as an au pair. My plan was to stay for six months and really study English and I ended up staying. I really loved it, I loved the ocean and being by the water. It’s hard for me to compare Italy to San Diego because I love both and my family is still in Milan and some in Tuscany. When I go back I get a chance to go back to both Milan and Tuscany, and I try to go back as much as I can.

What started you in the travel industry?

When I came to San Diego, I went to San Diego State University and studied anthropology there. Then life took different turns and after I had my son, I wanted to change things and the opportunity came up with Cultural Italy. That was about nine years ago and it was a perfect fit for me. At the time it was just Elena, Valentina and Alessia. And now we’ve grown so much. Of course I was new to the business at that time and I had a lot to learn. But I knew my country and I had that advantage. I have a passion to teach people and what I’ve experienced, and I know what I liked and what’s possible. So it was a good transition.

How do you ensure people have the best experience possible?

When I’m planning a trip, sometimes I have to take myself out of the equation. I put myself in other people’s shoes on how they would want to do things. This allows me to really custom tailor travel experiences based on their desires and that’s more important.

What is your most popular request?

If it’s a first trip to Italy, whether that’s a family trip, honeymoon, wedding, or trip with a group of friends, it’s usually the traditional Venice, Florence, Tuscany, Rome and the Almafi Coast. We have lots of honeymooners.

When it’s the second trip, people start asking for more suggestions and customizations. They’ll ask if they should do Lake Como or Almafi Coast, depending on type of year, Sicily or Calabria or what else they can see?

What are things that people are surprised about when traveling to Italy?

There’s a lot of things that people are surprised about. Like a private tour of the Vatican, yes it’s possible, it costs a lot. But even the simple things, like a balloon trip in Tuscany, they’ve seen it in the magazines but they think it’s out of their means.

What is one of your success stories?

There was a wedding that was really special. It was Jacqueline and Ray Leloup and we pretty much planned and arranged everything in Tuscany. The accommodations for the family, it was really beautiful and hearing they all had such a great experience, it was really, really special for me.

What is a tip you have for people when trying to plan their holiday?

Use an Italy travel expert. Whether it’s Cultural Italy or someone else, use an expert. When you’re trying to do it on your own it’s too overwhelming. People think they can do it and they just get overwhelmed and you really need an expert guiding you.

Is there a special tour or place that you would recommend?

I recommend Puglia and Calabria, really those are the places that I’ve been taking more trips too, but the southern part of Italy is really wonderful.

Interviewed by our blogger, Jennie Olson Six