January 25âFebruary 2, 2020
We called the Disney Fantasy our home for seven daysâand honestly, that still feels accurate.
This was our very first cruise. We went big. Balcony room. Extra experiences. Full commitment. We booked a Star Wars Day at Sea sailing, which meant we were sharing a ship with stormtroopers, Jawas, and a whole lot of adults pretending they werenât deeply thrilled about that.
No internet. No constant updates. Just ocean, schedules printed on paper, and being fully unplugged (except our cameras, of course).
Iâm piecing this together mostly from Facebook posts made after we got homeâbecause while we were on board, we were completely disconnected. Which, looking back, feels both luxurious and eerie.
âď¸ A Curveball Before We Even Left
A couple days before departure, Disney announced there was a mechanical issue with the ship. Tortolaâone of our planned stopsâwas officially off the table.
Instead, our itinerary shifted to include San Juan, along with the already planned St. Thomas and Disneyâs Castaway Cay.
We were bummed. Tortola was a big reason we booked the cruise in the first place. But there wasnât much to be done, and Disney offered onboard credit for the inconvenienceâso we accepted the trade and adjusted our expectations.
Sometimes magic comes with fine print.
⨠Boarding Day: Main Character Energy Activated
We flew into Orlando and took a bus to Port Canaveral, where everything immediately feltâŚelevated.
Upon boarding, our family was formally greeted and announced. Actual names. Actual fanfare. Immediate âoh, this is that kind of vacationâ realization.
Our stateroom was decked out in Star Wars dĂŠcor (an additional cost, but zero regrets). Weâd splurged on a balcony so we could sit and watch the open sea whenever we wantedâand we used it. A lot.
It felt indulgent in the best way.
đ˝ď¸ Life Onboard (and the People You Meet Along the Way)
We filled our days with presentations, workshops, live performances (Frozen, Pirates of the Caribbean, Star Wars), character meet-and-greets, wandering the ship like people who had nowhere else to beâand our weight in banana ice cream. Fully obsessed.
Disney cruise dining is rotational, meaning youâre assigned a dining time and sit with the same people every nightâso you actually get to know your tablemates.
We were seated with two other couples:
- An adventurous young couple from Indiana
- A young couple from Georgia who were veteran Disney cruisers and knew everything
It made dinners feel familiar. Like summer camp, but with better food and fewer trust falls.
đ´ Port One: San Juan, Puerto Rico
San Juan was our first stop.
My ex-husband and I stepped off the ship and immediately started melting. The heat was relentless. We wandered into town for a bus tour weâd booked, which helpedâbut aside from that, the one thing I really wanted to see was just too far to walk in that kind of heat.
So we pivoted.
We explored the market, grabbed something to eat, and headed back to the ship. It was actually nice returning when a majority of the guests were still out exploringâareas that had previously been overrun with families were suddenly easy to access, quiet, and almost peaceful.
đż Port Two: St. Thomas (with a Detour)
At St. Thomas, I thought it would be a good idea to take a boat over to St. John instead of exploring the island we were actually docked at.
On paper? Great idea.
In reality? Our tour turned into a half-hearted jungle exploration. Beautiful sceneryâabsolutely. But underwhelming overall. I think staying on St. Thomas wouldâve been the better call.
Travel lesson logged.
â Ashley Eckstein (A Very Specific Kind of Magic)
One of the absolute highlights of the cruise was Ashley Eckstein, the voice of Ahsoka Tano from Star Wars: The Clone Wars, being onboard.
We got to meet herâand we got to watch her take photos with the onboard Ahsoka, which felt wildly surreal in the best way. My boss at the time was obsessed with Ahsoka, so that was one of the very first photos I sent as soon as we had cell signal again.
For a Star Wars sailing, that kind of moment felt intentional. Like Disney knew exactly what they were doing.
đď¸ Port Three: Castaway Cay
Castaway CayâDisneyâs private islandâwas our final stop, and it delivered exactly what you hope it will.
We took a glass-bottom boat ride and saw a ton of fish, then made our way to the far side of the island to relax on the beach. No rushing. No schedule pressure. Just salt air and the feeling that this was exactly where we were supposed to be that day.
đŚ The Thing We Didnât Know Yet
Looking back, we think my ex-husband may have caught an early round of COVID while we were on the cruise. He was very sickâbut kept pushing through.
There were a handful of people wearing masks onboard, but at the time it didnât register as alarming. We were all still very much in the âoh, itâll be fineâ phase of collective denial.
A month later, the world shut down.
The timing is impossible to ignore now.
đ The Cruise That Almost Was
We had actually booked a second Disney cruise for October 2020. That one would have departed from New York City, ended in San Juan, and hit Bermuda, Tortola, and Castaway Cay along the way.
It was canceled.
COVID had other plans.
So Tortola remains the destination that keeps slipping through my fingers. Maybe someday Iâll get there. Maybe thatâs part of the story.
All I know is that the Disney Fantasy gave us seven days of escape, connection, and magicâright before everything changed.
And Iâll always remember it as the moment we were fully at sea, in every sense of the phrase.
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