Ashley O’Brien

Luxury Travel Coordinator

Ashley began her career as a financial advisor, quickly establishing herself as a top producer for nearly a decade. Her exceptional performance earned her the opportunity to experience incredible incentive trips with her branch and national colleagues.

After nearly 20 years in the financial services industry, most recently at Northern Trust, Ashley decided to pivot her career, combining her keen analytical skills and planning expertise with her lifelong passion for travel. Having enjoyed many business incentive trips and having accompanied her husband on luxurious law firm partner retreats, Ashley realized she wanted to create those same extraordinary experiences for others. For her, there is nothing more special than the joy and exclusivity of a luxurious company trip.

While Ashley is constantly envisioning her next travel adventure, she is also particularly obsessed with skiing in Vail, beach walks in Naples, visiting her Irish born husband’s entire family in Dublin, and throwing her arms around her 3 children as much as they will let her.

My Insider Travel Tip

Everyone has “their comfort thing” when they travel, and I always want to make sure that is thoughtfully included in my travel planning. Whether it’s making sure my husband has his ice-cold can of diet coke stocked in the refrigerator or having a yoga mat waiting for me our room, it’s that extra special touch of familiar comfort that helps us to relax in new surroundings.

My Travel Specialties

Every county in Ireland, luxury travel for young families, corporate incentive travel and partner retreats.

I worked with Ashley to plan our family’s spring break trip, and I could not have asked for a better experience. From our first conversation, Ashley took the time to understand our preferences, interests, and budget and then she tailored an itinerary perfect for each family member’s varied tastes. Ashley’s attention to detail and extensive knowledge of our destination really stood out. She provided insider tips and used her special connections to add a level of exclusivity that I didn’t know could exist on a family trip. Because of her efforts, our entire travel experience was smooth, stress-free and our family felt taken care of every step of the way. I would highly recommend Ashley O’Brien to anyone looking to plan their next adventure.

Jessica F. Winnetka, IL