Diana Tombolillo


Diana Tombolillo

Disney Vacation Planner Trainee - Vaughan, MT Canada

Hi, my name is Diana and I live near Toronto, Canada with my husband and two sons. My Disney addiction began when I was 14-years-old: my parents brought our family to Walt Disney World for the first time and we were all so impressed that we returned two years later. At 16-years-old, I was assigned the task of planning this vacation which included members of our extended family and I was beyond thrilled! Planning Disney vacations has been my passion ever since!

Living in Canada, it wasn’t always easy (or affordable) for my family to travel to Florida, but I was equally thrilled to plan vacations for other families and friends! I found joy living vicariously through the vacations of others when I wasn’t able to personally. Not much has changed since my teenage years, only that my passion and expertise for planning Disney vacations has grown stronger and ever more exciting!

My keen interest in peoples’ travel experiences never faltered, it actually led me to obtain a master’s degree in urban planning, (specifically, tourism development planning and urban design). I wholeheartedly want guests to love their travel experiences, whether at Disney or beyond. This all begins with a good plan!

Disney vacation planning can be overwhelming, especially for those who have never been, but that’s when an agent such as myself can be helpful! I am knowledgeable, organized, detail-oriented, and I am always eager to create itineraries for every vacation and budget (complete with “what if” scenarios). Although I strive for plans to be practically perfect in every way, there are sometimes unforeseen circumstances that can be easily managed if well-prepared. I am dedicated to making every dream (vacation) come true!

What exactly is it that makes Disney so special to Diana?

From the moment I visited Walt Disney World when I was 14-years-old, I was completely captivated by everything Disney.

Seeing Cinderella’s Castle for the first time left me awestruck: I was reminded of every Disney movie introduction I enjoyed as a child and it all came to fruition in that moment (you know, the movie intros featuring the castle and the instrumental “Wish Upon a Star” music?). To this day, every time I come face-to-face with the castle, I get teary-eyed and have that feeling of my childhood coming full circle! It’s so special!

In addition to the castle, the entire Walt Disney World Resort leaves me completely captivated. To me, it’s a well-functioning city built to dazzle and delight! The level of detail and theming is nothing short of amazing. I found it to be so impressive that I decided to pursue a degree in urban planning with the dream of someday working for the Walt Disney Company as an Imagineer. I yearned to be part of the magic somehow, someday I may get there!

Just when I thought that Disney couldn’t possibly be more impressive, I became a mother and now looking at Disney through a whole new lens. Traveling with children raised a lot of concerns for me, I was anxious about my son’s health, safety, and overall well-being when abroad. Being a Disney fan, we decided that my son’s first trip (at 5-months-old) would have to be to Walt Disney World. It not only provided everything I wanted: a safe and fun environment for the whole family, but it actually exceeded my expectations in terms of how Disney strives to make things so easy and convenient for guests of all ages. After all, Walt Disney’s original idea for a Magic Kingdom was to create a place where parents and children could have fun together…he definitely succeeded!

Traveling to Disney with children proved to be such a wonderful experience that my husband and I made the decision to invest in the Disney Vacation Club. For us, this was a means to enjoy a Disney vacation every year and create a lifetime of memories….our way of living happily ever after!