Holly Hueston Reinvents Greek Travel with The Living Greece Project

By the end of every trip to Greece, Holly Hueston and her husband, Vasilis, heard the same sentence from the friends and family traveling with them: “We never would have experienced this on our own.” They were not talking about famous landmarks. They meant the long lunches in tiny villages, the conversations with local people, and the olive groves that never appear in a guidebook. The sentence, repeated trip after trip, became the seed of a business.

Holly Hueston is the co-founder of The Living Greece Project, the small-group travel company she runs with Vasilis, who was born and raised on the island of Crete. Together they create immersive journeys that invite travelers to experience Greece as a friend rather than a tourist. A member of the Entreprenista League, Holly spent more than 3 decades in nonprofit finance and still serves as chief financial officer for a national nonprofit.

She never dreamed of becoming a founder. "Entrepreneurship isn’t really only about starting a business. It’s about solving a problem you care deeply about."

Here's how a recurring compliment from friends grew into a different way to travel:

A business that started accidentally

For most of her career, Holly built other people’s missions as a nonprofit CFO, work she genuinely loved. The idea for The Living Greece Project arrived quietly, through years of hosting friends and family in Greece and watching how differently they experienced the country with Vasilis as their guide.

Eventually, the couple asked themselves a simple question: What if they could create that experience for others? The company grew from there, a natural extension of who they already were.

Two founders, two sets of strengths

Holly and Vasilis divide the work along their strengths. He brings lifelong local knowledge, relationships, and cultural perspective from growing up in Crete, builds the website and customer systems, writes the weekly emails, and runs Facebook and Instagram. Holly brings strategic planning, operations, finance, and organizational leadership, sets up the systems and processes, and posts on LinkedIn and YouTube.

Their partnership tip is simple. “Respect each other’s expertise,” Holly says. “We don’t have to be equally good at everything. Trust grows when each person is empowered to lead in the areas where they bring the most value.” Both still work full-time while building the business.

Travel that feels like friendship

The Living Greece Project keeps its groups small on purpose, usually 6 to 8 guests, so every traveler feels welcome and known. Instead of rushing between landmarks, guests share meals, connect with local people, learn traditions, and discover the everyday life that makes Greece so special.

Holly’s travelers are curious, thoughtful people who value meaningful experiences over checking destinations off a list. Some have Greek heritage, some have traveled widely, and some have never left America. What they share is a desire to slow down and return home feeling like they truly experienced a place.

The win that matters most

Ask Holly about her proudest accomplishment and she doesn't reach for a metric. “It’s hearing guests tell us they arrived as strangers and left feeling like family,” she says.

Watching friendships form around a shared table, seeing guests grow confident in a new culture, and hearing them describe Crete as a place they will carry forever means more to her than any business number could.

Building slowly, on purpose

Holly and Vasilis have grown the company without outside investment, and they intend to keep growing thoughtfully rather than quickly. Building sustainably lets them make decisions based on the experience they want to create.

Her advice for aspiring founders comes from that same patience. “Don’t wait until you feel completely ready,” she says. “Start before everything is perfect. Listen carefully to your customers. Build relationships before transactions.” As a mother of 3 daughters and now a grandmother, she has learned there is never a perfect time to pursue a goal.

What’s next

The couple plans to keep offering intimate retreats in Crete while expanding their storytelling through videos, articles, and community presentations that help people experience Greece before they ever arrive. Over time, they hope to become known less as a travel company and more as a trusted bridge between visitors and the people, traditions, and everyday life of Greece, eventually reaching beyond Crete to other lesser-known corners of the country.

You can follow Holly on LinkedIn and explore the retreats at thelivinggreeceproject.com.

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If Holly’s approach to relationship-first travel resonates, the Entreprenista League is a community of women founders who value connection, shared experience, and practical business insight as they grow. Learn more about the Entreprenista League right here.