Ann Becker: travel guide, business consultant, and loyal Chicagoan

On a chilly Friday evening in October, we met with Ann Becker, founder of Travel with Ann- a Costa Rican adventure travel series. Ann discussed her lifelong affinity for traveling, her love affair with Costa Rica, and how she took her skills as an organizational/event development consultant (with over 35 years of experience) and applied them to her very own travel guide business. 

Multilingual Connections: Tell me about your background, where did you grow up and what was your family’s outlook on travel and exploration like?

Ann Becker: I grew up in Milwaukee. We traveled as a family but never out of the country and when I was growing up, that was pretty exotic. When I was a sophomore or a junior in high school, I started working for my dad to earn my own money so I could travel. In 1969, I went to Sweden and the bulk of the time, we were living with local families and integrating as best as possible into their lives. Part of the time when we were there, the kids from the States traveled to three different parts of Switzerland with our group leaders but also with Swiss kids who were around our age group. That shaped much of my thoughts about travel. While in graduate school at George Washington University, I worked with another student on a case study for a project that gave way to us studying in The Philippines and Thailand. We were supposed to prepare our research in a guesthouse where the researchers were stationed. We actually said we felt too far removed and found a way to move into the local community. As a traveler, I’ve always been about the local people and being off the beaten path. When you allow yourself to learn even a little bit of another language it just helps you connect more to a different culture.

MC: What is it about Costa Rica that first attracted you?

AB: I’d like to tell you that we initially did all of this research but that would be a lie. When my younger son was in high school, he suggested we go on an outdoor adventure. I knew a lot of families who had been with teenagers to Costa Rica and raved about how much fun it was. I thought there must be something particularly special about it.

MC: And what did you discover? What makes you keep returning to Costa Rica and encouraging others to come with you to experience it?

AB: I just really fell in love with it. We went to three areas of Costa Rica and the third was the Corcovado Peninsula, and so we left the little town to go by boat and I literally turned to my husband and said, “You know, I’m really in love”. After that initial trip, I turned around and took my 78-year-old mom there and after that, I knew I had to find a way to come back. I just love the people, the place, and the spirit of pura vida. It’s a spirit of happiness—live more, worry less. Take risks you would not take. The people are incredibly open and easy to get to know. They have a strong sense of family and a real sense of pride and country. Costa Rica is the oldest democracy in Central America and the only country that hasn’t had a civil war. They are really proud of their freedom.

MC: You host two different travels to Costa Rica each year- a Spanish Cultural Immersion and the Wonderful Women Adventure Trip. What is some of the feedback you have received from those who attend your Travel with Ann trips?

AB: With both trips I offer, there is always a home stay and that gets extremely high marks from everyone. I start with those in both my trips and people have a positive reaction to the grounding of that. One of my friends once wrote that she liked that I was in charge so she just had to worry about getting dressed and showing up. There is a luxury of that. I’m a real connector and networker and I have some incredibly deep friendships and relationships in Costa Rica. I like to try to weave in very localized experiences and exchanges and keep everyone thinking in a spontaneous, explorative way. There are a number of people who have traveled with me who have decided to do so because there children have grown and for the first time, they have a little more time and money flexibility and so this is a wonderful gift to themselves. I have more than one person who has come to Costa Rica who has been thinking about some major changes in their professional life and returned home with more clarity about what they want to pursue in their life. I think in every instance, people return with some very deep friendships.



MC: What are your plans for your business in the next ten years? What legacy do you hope to leave behind?

AB: For both my husband and I, we are in a place where we love what we do. I love the consulting work I’m still doing and I love my Costa Rica trips. I’m on the advisory board for a foundation there called the Fundacion Corcovado. And I’m on the board for the Elliot School at George Washington University. We are also at a time in our lives where we are both healthy and the idea of what we are doing in 5-10 years is not really in our brains right now! I think we will always have a strong foot in Chicago as we love it here. Traveling is important to us and we try to do it when we can but we still feel connected to the community. I spent so many years building strategic plans for my business and now it’s just me by design. I’m in charge now!


Ann will be leading two upcoming trips to Costa Rica and is currently still accepting applications for both including the ninth annual Wonder Women Adventure Trip which is scheduled for February 19th-March 2nd, 2014. For more information, visit Ann on the web at: