How We Create A Career: Experiential Travel Guide

Laura Frew hates traveling in tour groups. Which is ironic, because she is founder and director of Piccolina Adventures, a company specializing in designing and leading tour groups throughout Southern Italy. The difference, points out Laura, is that most tours turn you off to a place by shuttling you between sights. Piccolina Adventures, however, is focused on doing rather than just seeing. Says Laura, “we’re cooking and we’re tasting, we’re swimming in the ocean and biking, we’re laughing and we’re dancing and singing.” Whereas other tour groups put people to sleep, Laura aims to make them come alive.

Here she discusses the challenges of building a business on your own, the benefits of accepting the difficult and unexpected, and the value of following what you love – even if you’re not quite sure yet where it will lead.


When Laura graduated from college, she had no clue what she wanted to do next. She knew she had broad goals for herself–such as exploring her potential and gaining a greater understanding for how the world works–but had not aligned her coursework to prepare her for any career in particular. And, none of the traditional job options seemed like a good fit. Seeing as that she had studied Interdisciplinary Field Studies as an undergraduate at U.C. Berkeley (a major that allows students to design their own curriculum), it made sense that, after graduating, she would feel compelled to craft for herself a job that had previously never existed. The problem was envisioning what that job might look like.

Feeling like she had no other option, Laura decided to follow what she loved and see where it took her: “I didn’t have an end goal in college. I wasn’t necessarily trying to get from point A to point B. I felt that there was a point B somewhere, but I wasn’t sure what it was or whether I would find it. So the only things I could do were the things that I liked to do.” At that point, that meant traveling to Italy. She had studied abroad and fell in love during her Junior year in Siena and Bologna, and was itching to return. If she was smart, she thought, she could get someone to pay her to go. After an interview for a job leading tours for another company (a job that – finally – seemed so perfect for her that her mother declared that if it didn’t work out, it was fate) fell through, she decided “I don’t need you to do a bicycle tour through Italy. I’ll organize my own bike trip.” She succeeded.


She came home from 6 months of doing research and development in Italy after the trip, determined to plan another, and failed. Completely burnt out on academia, she spent a year working in construction, while learning about marketing. Then, while working in an Italian restaurant in San Francisco, she got the idea to design a trip for people like the patrons of the restaurant – people who loved Italy and food. Her tour of Puglia was born. She has now run several tours a year since 2008.

She describes the process of teaching herself how to build a business as incremental. “I had a product, and I was really excited about it. So I did a trip. And it worked. And then I came home. Then I did another trip. And then it worked. And then I came home. But there was no mechanism in place that worked consistently, so it was all case-by-case, crisis to crisis to crisis to crisis. That got tiring after a while, because the company was built on me and my energy and my passion – which is not sustainable. I realized I needed to get my software systems in place, and some sort of mechanism to make all this work. But I didn’t have any business skills, so I didn’t know what the hell that looked like! I didn’t have any money to pay a consultant to help me, so I limped by for another year or two. Finally, slowly, bit by bit, after talking to a lot of friends and figuring things out, I got a viable business model put together. I got a CRM and sales software and marketing automation. I’m finally coming out of this period where I was mired in my own growth. But it took a while.”


The end result, however, is a fulfilling career that is uniquely tailored to her skills and talents. “Piccolina Adventures was kind of a way to capitalize on all of the exploration and talking to people–finding out the best restaurants here, and asking people where their favorite place is there–that I do naturally, normally, and with so much joy and love.” It turns out the career is also the manifestation of a forgotten dream; while cleaning her attic recently, Laura stumbled upon the poster she had created for her senior project – she had worked with a travel agent to design bicycle tours throughout Italy.


Her favorite aspect of her work is the necessity of thinking creatively. “The thing that I like the most – even more than I like biking through Sicily and drinking wine with people–is building a company. It is so interesting to me, managing all the crazy challenges that come up, and figuring out how to creatively solve a problem when you have no resources.”

Case in point: In 2010, Laura received a contract from 21 cyclists in San Francisco and San Diego, asking for a tour. At that point, Laura did not own a bike. She enjoyed cycling, but did not feel prepared to propose the types of serious routes in Sicily that the group wanted. So she contacted local cycling groups in Sicily. The result: The cyclists became honored guests. “We arrived in Palermo and this guy who works for the Sicily cycle tour association met us. He helped me do the initial orientation, he chose the route for the next day, drove us with his car. He connected us with the mayor of Monreale, and we had the most amazing reception in the piazza of Monreale, with the most exquisite pastries I’ve ever eaten in my life. I eat a lot of pastries. These were hands down the most exquisite cannoli I’ve ever had. So we got this crazy reception in one of the most beautiful towns in Sicily. And that’s where we started the bicycle tour. He guided us on this amazing route, and then dropped us off at the hotel. And that was it. That was the last we saw of him. The next day we were friends with the Alcamo cycle touring team, which lived close by. They came and they hosted us and they took us on this amazing ride and it finished in a farmhouse, with these women who were making cheese. We tasted cheese. And then we had lunch all together. It was very much a peer-to-peer bonding experience – both for the Italians and for the Americans. 20 new friendships started.”


Not surprisingly, many of the participants on her trips describe the experience as life changing. For example, Laura recounts the experience of an owner of a San Francisco Italian restaurant: ” ‘The second day, the guide took us to his mom’s house–a mansion in the hills, near the sea. And she cooked us lunch – this amazing huge Sunday meal with the guide and his entire family.’ To be able to be welcomed like friends and family in an area that you are totally unfamiliar with is a really really special experience for everybody. It’s the kind of experience that everybody tries to sell, but you can’t mass produce an experience like that.”


Laura’s travel philosophy is three-fold:

1. Personal Connection: I like things that are personal and real and not standardized. All the places we stay at have a lot of character and really sweet owners, who are very happy to host us.”

2. Participation: “I hate tours. I hate traveling with my family. And I hate traveling in groups. They just make me really bored. Following people around, I totally turn off to the place I’m in. And sitting in a bus sucks. So I wanted to put together a trip that people would be excited to take. That would engage people, that would make people want to participate in where they were. On our tours, nothing is being shown to you. You’re participating in everything.”


3. Spontanaeity: “What creates memories and what creates favorite moments isn’t necessarily what’s smooth and easy. If there’s a guy in a black jacket that meets you at the airport and takes you into his cushy Mercedes and drives you there, you’re not engaging in anything . If I come home, and I felt comfortable, and I never felt not at ease, my trip doesn’t have that much flavor somehow, is how I feel. So I don’t mind a little bit if people are a little uncomfortable. I don’t mind if things get a little crunchy. Because, it’s tough, but it makes people really open up. The place enters into you more.”


For example, she recounts how one of her fondest memories from a trip stemmed from a 3am wake up call. “One night when we were near Gallipoli, we stayed in these ancient conical structures that were built in the prehistoric age. The farm that had these structures had a big party that night, and they invited us to join their party, so we were dancing with everybody and it was really fun. I had met their son, who was a wine maker. And I had brought him three white wines from California, and he was really happy. We all had a wonderful party and went to sleep. And then at 3 in the morning, outside of our door, I hear ‘boom boom boom boom.’ We said to each other: ‘what’s going on?’ I stumbled out of the room, and there is Glauco and 5 other of his friends, with three tamborines, two guitars, everybody’s singing. They came and they were singing all these traditional songs for us and the ‘boom boom boom’ was the tamborine. They were singing us a serenade. We all went back to their house and played music and sang and drank wine until 4 in the morning.That was pretty memorable.”


Her career advice in general? “Do what you love. What you love to do, you also generally are good at, because you’re passionate about it. And what you’re talented at, you can develop into a very special skill. Because you love it, and you’re good at it, that’s something that nobody else has.”


Thank you, Laura, for offering insight into the process of constructing Piccolina Adventures! I am in awe of how you built your dream from scratch, how you brought into existence a job for yourself that encompasses your skills and passions. It is clear that your love for your work shines through your trips, and touches the people who take them. Here’s to the continuing evolution of Piccolina Adventures!

For more interviews with women who are forging their own paths, career and otherwise: Follow me on twitter @shespoised or like She’s Poised on Facebook (and select Get Notifications from the drop down menu).

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