Ashley Courington
Blending luxury, wellness, and sustainability, Ashley Courington creates transformative travel experiences that connect her clients with nature — and with themselves.
Oxford, Maine • 1 Year as a Travel Advisor
The Spark Behind the Journey
My love of travel started early, passed down from my mother and grandparents. Even though many of our trips were domestic, every new place we visited sparked curiosity and excitement. That early exposure created a lifelong passion for exploring new destinations, cultures, and experiences. Over the years, that love never faded—it just waited for the right time to become my career focus.
Finding Her Path
I studied Tourism Management in college, but my career path initially led me into event planning and later into technology sales. While those roles were rewarding, they didn’t feed my passion, and eventually I found myself feeling unfulfilled. During conversations with my best friend, who’s also a life coach, we kept coming back to the same thing: travel was always what lit me up. She had recently interviewed Haley on her podcast and encouraged me to reach out. I did, and that connection reignited everything I loved about the industry. From there, my career in travel truly began.
Overcoming Challenges
The biggest challenges I faced starting out were self-doubt and learning to adjust to being my own boss after spending 20 years in very structured corporate environments. I constantly questioned whether I had made the right decision and if I could really make this work. The fear was valid and very real, but it ultimately proved my resilience. For two decades, I poured my energy into someone else’s success and now I’m doing it for my own. While that comes with risk, it also brings incredible reward.
Proudest Moment
My proudest “wow, I did that!” moment was taking the leap into destination weddings. With a background in event and wedding coordination, it felt like a natural fit—but it also pushed me into an entirely new realm of planning. Instead of managing timelines and day-of logistics, I found myself negotiating room blocks, coordinating group transfers and excursions, and serving as the main point of contact for dozens of travelers. It was a brave step that combined my organizational strengths with my passion for travel, and seeing everything come together seamlessly for couples and their guests has been incredibly rewarding.
Training That Made a Difference
The week-by-week training videos have made the biggest difference. It’s incredibly helpful to be able to go back and watch them in real time while working through my first few bookings. Having that step-by-step guidance and reassurance has been such a confidence booster.
Life Today
It has changed in the best way! I now have the freedom to create my own schedule and design my days around what works for me. If I want to take a day off, I can. If I didn’t sleep well, I can start my day later. If it’s sunny and I want to take the dogs for a long midday walk, I can shift my work to the evening or another day. The beauty is that I get to choose. It’s on my terms for the first time ever, and that feels amazing. The only challenge is learning when to stop, so I don’t burn myself out.
Advice for New Advisors
The beginning is hard! Those first few proposals can take a lot of time, but have faith in yourself and trust your training. Within 3 to 6 months, you’ll start to find your rhythm as you learn which booking engines you prefer, which vendors fit your style, and what types of clients you enjoy working with most. Each new client is an opportunity to grow and refine your process. Most importantly, be patient with yourself in the beginning. It can feel overwhelming at times, but stick with it. It gets easier, and it’s absolutely worth it!
What’s one travel destination that completely stole your heart?
Every destination I visit completely steals my heart! I’m that person who looks at real estate listings while on vacation, imagining what it would be like to move there someday. My travel wish list grows with every trip I take and with every itinerary I plan for my clients. It’s both a blessing and a curse, but I wouldn’t have it any other way!