Keegan Cross

Specialties

Fueled by a profound love for global exploration cultivated over a lifetime of immersive travel, Keegan crafts journeys with expert precision and a deeply personal touch that turns each trip into a lasting memory.

Originally from Denver, Keegan lived in Durham, North Carolina, and New York City before ultimately calling Atlanta home. His global mindset was shaped by transformative study abroad experiences in London and Greece and over twenty years of family travels to Mexico. For Keegan, travel is more than just visiting iconic landmarks or staying at world-class properties; it is a force that has shifted his perspective on the world. Experiencing diverse cultures and embracing the unfamiliar has brought him immense personal growth and joy—a gift he now strives to share with his clients.

Keegan’s corporate background at J.P. Morgan Chase and IBM honed his ability to manage high-stakes projects, navigate complex logistics, and deliver exceptional service—skills that now fuel his success in the travel industry. After thriving in a demanding corporate setting, Keegan deeply understands that his clients have limited time and mental bandwidth to dedicate to highly nuanced trip planning. He takes pride in taking the entire planning process off their plate, so his clients can focus on the best part: dreaming, anticipating, and savoring every moment of their journey. Rooted in the belief that travel should be as effortless as it is inspiring, Keegan takes immense pride in curating experiences that perfectly reflect his clients’ individual interests, lifestyles, and dreams—often sure to include a few unforgettable surprises along the way.

Having explored over forty-five countries and counting, Keegan possesses an intimate knowledge of destinations and their cultural nuances, in turn ensuring a trip’s success from conception to execution. A true people person, Keegan thrives on building relationships and surrounding himself with inspiring individuals from all walks of life—a skill that gives him a unique ability to tailor trips to every kind of traveler. Whether planning a luxury safari honeymoon in South Africa, a privately guided backpacking trip through Peru, or finding the perfect villa for an extended family in the French countryside, he settles for nothing less than bringing his clients’ exact vision to life. Keegan’s travel philosophy is rooted in precision, passion, and genuine connection.

Which destinations or hotels do you go back to again and again? Why?

Italy! What’s not to love? I’ve explored Italy on over six trips, yet each visit still feels like the first—filled with excitement and wonder. From playing in youth soccer tournaments to getting married in Capri, Italy holds a special place in my heart. There’s always something new to discover: a charming village, a hidden trattoria, or a piece of history waiting to be uncovered. The warmth of the people, the beauty of the language, the incredible food, and the depth of the culture keep drawing me back; it’s a place that never stops surprising me.

What does your perfect vacation day look like?

My perfect vacation day begins the moment the pressure is off—after the major sights have been seen. It’s that freedom-filled day that follows, when there’s no itinerary, no must-see checklist, just time to truly experience the destination. I love wandering aimlessly through side streets, letting curiosity—not Google Maps—guide the way. It’s about stumbling upon a quiet piazza, browsing a local shop, or discovering a hidden café that wasn’t in any guidebook. I’ll stop for a glass of wine, sit outside, and simply take it all in—the pace of local life, snippets of conversation in another language, the subtle rhythms of a place being itself. It’s unhurried, unscripted, and all about presence. For me, that’s when travel becomes more than sightseeing; it becomes a memory and a feeling.

Travel Tip

  • Focus on the overall experience or traveling, not just checking off a list of sites. If you love a destination, you can always return and explore further. Don’t let the pressure to ‘see everything’ turn your trip into a race. Build in time to explore, unwind, and simply enjoy. You’ve gifted yourself a break from the pace of daily life so make space to relax and take it all in.