Wendy
Simmons

I've traveled to over 100 countries across all seven continents — from the North Pole to the South Pole to the Pole of Inaccessibility. I took my first solo international trip at 12 to visit a girl I barely knew in Mexico City. Remarkably, my mother let me go. That summer changed my life and set me on a path of insatiable curiosity for the unknown. I’ve long been drawn to the edges of the map — the places rarely seen or easily reached — but decades of travel have filled in everything between, too. My journeys span the world’s wildest outposts and its most beloved destinations, offering a full picture of what makes travel transformative.

This depth of firsthand experience — from months-long stays to making the most of extended layovers — shapes how I guide others. I’ve traversed the Sahara Desert in Chad and the Salar de Uyuni in Bolivia, trekked through the remote jungles of the Congo to track elusive mountain gorillas and across the icy expanses of Antarctica to visit penguins in Queen Maud Land, spent time with some of the world’s most isolated tribes, and traveled to breakaway regions not even recognized as countries. Whether sleeping under the stars in the Danakil Depression, one of the most extreme places on Earth, or welcoming the New Year under the watchful gaze of the ancient Moai statues of Easter Island, I've long found joy in adventures that ask us to be awake, alive, and engaged. This firsthand knowledge of both the spectacular and the logistical makes me uniquely equipped to help clients experience the world in ways that are extraordinary and deeply enriching.

Before becoming a travel advisor, I built a 25+ year career as a CEO, brand strategist, and communications executive, leading global campaigns and building cult-favorite brands. My background has trained me to listen deeply, solve problems quickly, and communicate clearly. These skills now help me create exceptional travel experiences that are thoughtful, organized, intuitive, and seamless.

As a bestselling author (My Holiday in North Korea: The Funniest/Worst Place on Earth — named one of the "19 Travel Books That Will Change the Way You See the World" with over 25,000 copies sold), travel writer for Travel + Leisure and Huffington Post, and award-winning photographer, I know how to craft stories — and journeys — that resonate. My photography is defined by honesty, empathy, and restraint, capturing unposed moments that reveal what's genuine and human. I approach travel itineraries with that same eye for authentic, meaningful experiences.

I don't just plan trips — I create experiences that allow people to feel more alive, more connected, and more themselves in the world. Whether I'm curating a solo retreat in the Japanese Alps, crafting a multi-country African safari, or helping someone fall in love with the art of travel for the first time, I bring rigor, imagination, and joy to the process. I am meticulous with details and generous with care, knowing that the smallest moments — the unexpected conversation, the hidden courtyard, the extra day you didn't plan for — often become the most lasting.

Travel is not just what I do. It's how I see. It's how I move through the world. It's the lens through which everything else in my life makes sense.

Let's plan something extraordinary.