In a world where everyone seems too busy to travel, Ross Alcorn is proving that adventure doesn’t require unlimited free time—it simply needs strategic planning and the right mindset. As founder of Itinerary Boss, Ross has transformed his decade of travel planning experience into a framework that helps busy professionals create unforgettable journeys without sacrificing their careers.
Photos Courtesy of Ross Alcorn
Ross’s travel journey began in childhood when his mother put him on skis at age four. These early adventures instilled a sense of curiosity and fearlessness that would shape his approach to life. However, it wasn’t until 2015 that Ross’s reputation as “the travel guy” truly began to take shape. When none of his friends wanted to plan their group trips, Ross stepped up, meticulously organizing snowboarding excursions to Colorado that eventually expanded into annual European adventures spanning multiple countries.
What sets Ross apart isn’t just where he’s traveled, but how he’s managed to do it while maintaining a demanding career in healthcare sales. After experiencing burnout from balancing work, travel, and attending nine weddings in a single year, Ross recognized a common challenge: most people struggle to prioritize personal adventures amid professional responsibilities. This realization became the foundation for Itinerary Boss, a travel company built specifically for busy professionals who want meaningful travel experiences without the stress of planning.
The heart of Ross’s approach combines financial strategy with practical efficiency. Rather than booking trips for clients as a traditional travel agent might, Ross equips travelers with frameworks for maximizing credit card rewards, strategically timing bookings, and avoiding the overwhelm that comes from endless internet research. His methods have helped travelers—including himself—save thousands on trips, including $18,000 on his upcoming honeymoon to Thailand and Bali.
Ross’s own travel stories highlight both the unexpected joys and challenges of adventure. From accidentally flying off the back of a boat in Croatia to unexpectedly encountering the Croatian president, his experiences demonstrate how stepping outside your comfort zone creates unforgettable memories. Even mishaps, like his friend forgetting Amsterdam “souvenirs” in his bag at airport security, become cherished stories that connect travelers to places and people.
For those looking to incorporate more adventure into busy schedules, Ross offers practical advice: be strategic with planning, giving yourself and friends plenty of lead time; don’t try to please everyone with dates and destinations; understand your budget constraints and plan accordingly; leverage credit card rewards to offset costs; and most importantly, recognize that saying yes to travel means creating memories that will outlast any material possession. 
The most valuable insight from Ross’s journey is perhaps the simplest: adventure isn’t something that happens when you have more time—it’s something you prioritize despite constraints. By approaching travel with curiosity, preparation, and flexibility, even the busiest professionals can create meaningful experiences that enhance rather than compete with their careers and responsibilities.
Whether you’re planning a snowboarding trip with friends, a romantic getaway with a partner, or a solo adventure, Ross’s framework offers a roadmap for turning travel dreams into realistic itineraries. After all, as he puts it, those who wait for the “perfect time” to travel may find themselves with regrets rather than memories.
