Boots on the ground.

Insider Expeditions takes great pride in having one of the most experienced and talented teams in the industry. Together we speak over seven languages and include alumni from Yale, Harvard, Princeton, MIT, Stanford, Columbia, UC Berkeley and other top educational institutions in the country.


IMG_4198Carl Shephard, Founder and Chairman

Carl has developed and directed over 500 customized educational travel programs across six continents. He began his service in enrichment travel in South America with a local tour operator, leading cultural exchanges, service projects, and innovative travel itineraries throughout the region. Carl then moved to Japan and worked for Peace Boat, eventually serving as their Director of Program Development for international educational voyages.

Before co-founding Insider Expeditions, Carl designed the in-country academic field programs across 14 countries for The Scholar Ship, a semester abroad program that brings students from around the world to live and study together on a seafaring voyage.

Carl graduated Phi Beta Kappa from Yale University and earned a Masters in International Relations while serving as a World Peace Fellow in Tokyo.


Christopher+Shephard

Christopher Shephard, Co-Founder and President

Chris has developed extensive travel itineraries throughout Europe, South America, the Middle East and Central Asia. In addition to serving as a tour program leader, Chris has spent much of his international working life seeking to improve the conditions of developing countries. He has served the United States Agency for International Development in both Iraq and Afghanistan, focusing on education and health issues in those countries. Chris began his career as an experiential educator and tour leader, directing programs for the Princeton Blairstown Center.

Chris earned his BA from Princeton University and holds a Masters in International Development from the Johns Hopkins School of Advanced International Studies.  He is currently working on a Ph.D. in International Education at Columbia University.


IMG_5391Jordan Valdés, Chairwoman of the Board

As Chairwoman of Insider’s Board, Jordan’s involvement ranges from developing and maintaining Insider’s relationships in Cuba, to identifying strategic Insider partnerships and crafting new Insider adventures across the Cuban island. With unparalleled connections at home and abroad, and a unique ability to problem solve in even the trickiest scenarios, Jordan’s value to the Insider board is a linchpin for its success.

Jordan has lived around the world, with extensive professional and travel experience across Europe, the Middle East, Asia, and Latin America. She is also a passionate policy advisor, and served as President Obama as a senior advisor in the Office of International Trade in the Small Business Administration (SBA). Prior to her work at SBA, Jordan advised the US Agency for International Development (USAID), the Department of Energy (DOE) and the World Bank in various projects from Latin America to Africa to Bangladesh, on issues ranging from carbon finance to supply chain and logistics. Oh, and she has served as a Senior Advisor to the Prime Minister of Bahrain. Jordan is fluent in Spanish and French and conversational in Arabic and Italian.


Mary Bruce, Director, Special Projects

Mary has more than a decade of experience directing creative travel itineraries, major events, as well as strategic planning for national nonprofits. She’s traveled the globe, worked with media from Al Jazeera to NPR, and has specialized in customizing service-learning experiences domestically and abroad.  Mary’s first trip overseas was in high school, visiting Strasbourg, France, where she learned the benefits of living above a bakery, especially one just a short drive from the largest beer cask in the world.  She also lived in Morocco for two years while serving in the Peace Corps.

Before joining Insider Expeditions, Mary was the Co-Executive Director of AmeriCorps Alums, supporting 1 million alumni to plan their own life’s adventures and designing affinity experiences for an incredibly diverse membership base. She studied Arabic, Spanish, French, imiq Tamazergt, and ilan Tagalog. Mary graduated with highest distinction from the University of Virginia and also received her MPA from the Woodrow Wilson School of Public and International Affairs at Princeton University.


IE profile picDaniel Peterson, General Counsel

Dan serves as an outside general counsel for small businesses and non-profits. He specializes in assisting organizations with outsized legal needs, such as B2B companies and those in regulated industries (like travel companies operating in Cuba under exceptions to the U.S. embargo). His other clients include auction experts, biotech geniuses, and pinball wizards.

Dan graduated from Yale University and the Georgetown University Law Center. In between, he taught scuba diving on the Great Barrier Reef and sailing in the Caribbean and Hong Kong. Dan is currently on hiatus from international travel until his two daughters are old enough to carry their own stuff.


CherineHeadShot3Cherine Badawi, Trip Director

In search a wild and well-lived life, Cherine has lived extensively in six countries and traveled to more than 50. Her work has ranged from strumming guitar on street corners to working as an international journalist to serving in the United Nations. She especially enjoys planning exceptional travel and cultural programs for younger groups.

Highlights of Cherine’s past professional experience include writing Footprint’s Travel Guide to Egypt and serving as a senior trainer for Challenge Day, an innovative peace program featured on the Oprah Winfrey show and MTV. Cherine also served as the Curriculum and Training Director of The Mosaic Project and worked as the Experiential Education Specialist of a transnational floating university, The Scholar Ship. Most recently Cherine had the privilege to speak at a UN High Level Forum on The Culture of Peace.


Nate 2Nate Hodson, Trip Director

Nate is a PhD candidate in Near Eastern Studies at Princeton University,  and has spent a great deal of the past decade on the road. His first trip to the Middle East was to Morocco in 2003, and he’s since been to nearly every Arabic speaking country (highlights include Oman, Saudi Arabia, Syria and Yemen). He’s also traveled widely outside the region and has collected a story or two from Pakistan, India, Laos, Colombia, Brazil, the Galápagos Islands, among other places. Nate appreciates fixed prices, but in a haggling situation he has a pretty keen sense for when a merchant has accepted his “final offer.” He speaks Arabic well and occasionally takes steel wool to his rusty German, French and Persian.


Miranda GaleMiranda Gale, Trip Director

Miranda has over seven years of travel and event management experience, including three years at the Freer Gallery of Art and Arthur M. Sackler Gallery, the Smithsonian’s museums of Asian art. From glamorous gala dinners to after hours art evenings to exclusive behind-the-scenes tours, Miranda is no stranger to planning and executing complex logistics.

Originally from Golden, Colorado and an alumna of American University’s Kogod School of Business, Miranda’s interests include yoga, mountain hiking and skiing, the performing and fine arts, photography, and naturally, international travel. 


IMG_0204Joanna Strange, Trip Director

Joanna is a person with intense wanderlust. She grew up traveling regularly to the Middle East and she has lived in London, Edinburgh, Berlin and Dublin. This year, her one-year-old, Leo, took his first international trip to Milan.

Joanna’s creative mind has not just directed travel itineraries – she has directed film, television and theatre productions as well – all of which though have happily required extensive abroad.  Additionally, Joanna is an expert in perhaps the most international city in the world.  As a licensed New York City tour guide, she can take anyone to the hottest and most little known spots across all five boroughs.


1345df64-82e8-4f40-b091-5ee1c05cf69dDara Goldberg, Logistical Mastermind

Dara has over five years of sales and marketing experience with an international hotel chain with luxury and boutique and funky hotels across six continents. She thus can help our clients choose the very best of places to stay, no matter where we are traveling. Dara is also an active volunteer with several charities that assist the homeless and the blind and she is passionate about animals. She is currently an avid student of improv comedy and a lifestyle blogger to boot.


Alex Boxer, Creative Genius 

Alex is a physicist by day and a travel guru by night. As an expert in oceans and ocean technologies, he has traveled extensively both above and below the waves throughout the Pacific, the Middle East, and Europe. Alex has a passion for technology from all eras, from modern neural networks to medieval astrolabes.

Alex holds a Ph.D. from MIT in plasma physics, an M.Sc. in the history of science from Oxford, and a bachelor’s degree in classical languages from Yale. He is pretty much the smartest person we know, which helps to put unparalleled, unexpected surprises via his creative genius into every single program.


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