My journey to working on a cruise ship started years before I ever set foot onboard. In 2017, I spent a magical year at Walt Disney World as part of the Disney College Program — and I absolutely fell in love with it. When the program ended, I knew I had to find a way back to the world of Mickey Mouse.
Fast forward to 2019 — that dream came true when I was hired by Disney Cruise Line (DCL) and began my very first contract at sea!
CONTRACT Log
Contract: 1
Year: 2019
Ship: Disney Dream
Countries Visited: United States – Bahamas – Mexico
Applying to Work for Disney Cruise Line
The application process was faster than I expected. I found an opening for the Bibbidi Bobbidi Boutique position on the DCL careers page, applied online, and was quickly invited to an interview. Within a few weeks, I received the magical acceptance email — cue the happy tears!
💌 Receiving that email and realizing I’d be working for Mickey again was one of the happiest moments of my life.
Pre-Boarding & Visa Process
Before setting sail, there were some important steps to complete:
- A full medical examination
- A trip to the Australian Embassy in Sydney to get my seaman’s visa
It all felt surreal — one minute I was filling out paperwork, and the next, I was packing my bags and preparing for life at sea! (Here’s my guide on how to pack for a cruise ship contract!)
⚠️ Note: I applied in 2019. The process may differ now, especially depending on your home country. Always apply through official channels and check the Disney Careers website to avoid scams.
First Week Onboard the Disney Dream
Disney Traditions
Before joining the ship, all new hires go through a few days of training on land. This includes “Traditions,” the magical orientation class that introduces new Cast Members to the Disney legacy. It was my second time experiencing it (thanks, Disney College Program!) — and it was just as magical the second time around.
Wet Drill
One of the more intense (but fun!) pre-ship requirements was Wet Drill — officially known as Personal Survival Techniques Training. Think: life jackets, immersion suits, swimming in open water, and flipping life rafts. Yes, it’s called “Wet Drill” for a reason!
Embarkation Day
After land training, it was time to officially join the ship. I proudly wore my “Earning My Ears” red tag and stepped onboard the Disney Dream for my very first embarkation day. We toured the ship (and I got completely lost — multiple times!), sat through hours of safety and HR training, and attended Safety Familiarization — the first of many.
First Week Onboard
That first week was a blur of:
- Navigating the maze-like crew hallways
- Attending department trainings
- Getting lost (a lot)
- Starting my first real shift at the Bibbidi Bobbidi Boutique
Everyone was so kind — any time someone saw my red tag and confused expression, they jumped in to help. It made such a difference!
Working in the Bibbidi Bobbidi Boutique
I joined the magical world of the Bibbidi Bobbidi Boutique as a Fairy Godmother in Training (now called a Fairy Godmother’s Apprentice). My job? Transforming children into princesses and royal knights — complete with hairstyling, makeup, storytelling, and lots of pixie dust.
On Pirate Night, the boutique transformed into the Pirates League, where we gave guests fierce pirate makeovers — think black eyes, scars, and shouting “Walk the plank!”
This role was technically part of the Merchandise Department, so I also got to work in the onboard shops occasionally.
✨ By the end of each shift, I was coated in glitter — and I swear I’m still finding pixie dust in my socks years later!
Highlights From My First Contract
Once I found my rhythm, I absolutely fell in love with ship life. Here are a few of my favorite moments:
- 🌅 Watching the sunrise over the ocean — and seeing dolphins!
- 🧑🏫 Becoming a Disney Trainer
- 🏆 Competing in the DCL Games with my team (a fun, friendly crew competition)
- 🍫 Trying my first Palo chocolate soufflé (#iykyk)
- 🌪️ Experiencing a “hurricane cruise” — we had to reroute and ended up in Mexico!
- 👑 Reenacting The Princess Diaries while transforming a Guest named Mia
- 🤍 Wearing officer whites for the first time!!
My First Step-Up: Guest Communicator Role
Near the end of my contract, a dream opportunity popped up — a step-up to the Guest Communicator role, which involved managing all the onboard digital and print communication. I applied and got it!
This one-month role was the stepping stone to what would eventually become my full-time career with Disney Cruise Line.
End of Contract
Seven months later, my first contract came to a close. I had survived seasickness, safety drills, homesickness, and so many challenges — and I loved every minute of it.
This contract was the beginning of a brand new chapter in my life — and one I’ll always treasure.
Disclaimer: Disney Cruise Line is the only cruise line I’ve worked for, so I can’t speak of the experience with other cruise lines. All opinions in this post are my own and not affiliated with Disney in any way.
🚢 More Ship Life Posts
Check out more of my contracts from life at sea:
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Jess at Sea 
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