Jess at Sea

Welcome to Contract 2—a chapter of my Disney Cruise Line journey that had a little bit of everything: three ships, two job roles, a bunch of new Caribbean ports, and oh yeah… I got stuck onboard during the start of a global pandemic. Casual, right? 😅

Contract Log

Contract: 2
Year: 2020
Ships: Disney Dream → Disney Magic → Disney Fantasy → Disney Magic (again!)
Countries Visited: USA, Bahamas, Mexico, Cayman Islands, Jamaica, US Virgin Islands, British Virgin Islands, England

Back for Round 2!

After my magical first contract at sea, I couldn’t wait to dive into my next one. I knew there would be more adventures ahead—but I had no idea just how memorable this one would be. Spoiler alert: it involved transfers, transformations, and a global shutdown!

Returning to the Disney Dream

My journey began with a 30-hour flight from Australia (hello, jet lag), landing me in Orlando the night before embarkation. As a returning crew member, the process was a little different—straight to the hotel, pick up my welcome packet, and get ready for that 5 a.m. wake-up call. It was back to business the next day with Safety Fam, cabin assignments, costume pickups, and—bam—I was back in the Bibbidi Bobbidi Boutique, transforming little royals like I never left.

Honestly, I was nervous I’d forgotten how to do an enchanted bun. I hadn’t. It was all pixie dust and muscle memory. ✨

First Christmas at Sea

Spending the holiday season onboard was every bit as magical as you’d imagine. The atrium glittered with lights, and the giant Christmas tree made everything feel cozy and festive. Working in the BBB meant I was right in the middle of the magic.

Ship Transfer #1: Disney Magic

Early in the new year, I accepted an offer to transfer to the Disney Magic as a Merchandise Host. While I was excited for the opportunity, the transition was… rough. I missed my friends, my role in the Boutique, and navigating a new ship with new routines was overwhelming.

But! The silver lining? New itineraries! Unlike the Dream’s Bahamas loop, the Magic took me to:

• Key West (Key lime pie and giant chocolate chip cookies = yes please!)
• Cozumel, Mexico (my nacho obsession began here)
• Grand Cayman & Jamaica
• Parasailing in the Bahamas!

Still, I realized my heart still belonged in the Boutique, so I put in a transfer request…

Ship Transfer #2: Disney Fantasy

…and I got it! Back to the land of glitter and tiaras on the Disney Fantasy, sister ship to the Dream. This transfer felt like a homecoming. I knew the layout, I knew some of the crew, and I finally felt like myself again. Bonus: my new roommate became one of my best friends (we even traveled to Iceland together later!).

New ports included the Virgin Islands (St. Thomas by cable car = stunning) and more Caribbean goodness. Life was good. And then…

The Pandemic Hits

Cue dramatic music. Just weeks into my time on the Fantasy, the world flipped upside down. One minute I was sprinkling pixie dust, the next… global lockdown. What we thought would be a 2-week pause turned into an indefinite standstill.

I had reached the end of my contract, but I couldn’t fly home. So I stayed onboard in “Guest Mode.” A small group of us kept busy running our own activities, soaking up sunshine on the open decks, and doing our best to stay positive. Thankfully, our ship had zero COVID cases, so we lived in a bit of a floating bubble.

Ship Transfer #3: Back to the Magic (Again!)

Eventually, Disney arranged a massive crew shuffle to get us all home. I transferred back to the Magic (my third ship of the contract!) and we sailed across the Atlantic to England so I could catch a flight to Australia.

Crossing the Atlantic by cruise ship during a pandemic? That’s one for the memory books.

Contract Highlights

• First time working on three different ships in one contract
• First Christmas and New Year’s onboard
• Exploring new ports like Cozumel, Key West, and the Virgin Islands
• Going parasailing in the Bahamas
• Getting stuck at sea during the start of the pandemic
• Crossing the Atlantic by cruise ship
• Making lifelong friends along the way

The Journey Home

The trip home was… long. Add a two-week quarantine (with army escort!) once I landed, and it truly felt like a movie. Onboard, we had been in such a bubble that I didn’t grasp the gravity of the pandemic until I touched down in Australia.

And then came the waiting. Months turned into a year. All I wanted was to get back to my dream job. Every day, I checked for updates, hoping for the magic words: “Welcome back.”

And one day… I got them. 💌✨

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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.

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