Dead Rooms Tell No Tales: Caribbean Beach Pirate Retirement

Dead men tell no tales. If ye be brave or fool enough to face a DVC curse, proceed.

Walt Disney World has released 2023 vacation packages and resort reservations, and one room category was absent from the resort roster: Pirate Rooms at Disney’s Caribbean Beach Resort. Nothing was available from January through October 2023, and the rooms weren’t even listed as unavailable. Vanished as if they never even existed.

The company followed up with a statement during the Walt Disney World travel agents webcast indicating that the Pirate Rooms at Caribbean Beach Resort were being discontinued. Disney also announced that the no new theme is planned to replace the Pirate Rooms “at this time.”

To some extent, this is totally unsurprising. The Pirate Rooms are more controversial among Walt Disney World fans than Captain Jack Sparrow. The beds are among the most uncomfortable we’ve ever slept in, although if I’ve learned anything recently about beds, it’s that they can always be made more unpleasantIn retrospect, I guess I’ve gotta commend Disney for not getting too authentic with these ships and giving them a poop deck. That definitely would’ve made them worse!

Joking aside, the Pirate Rooms are actually infamous. Our original Caribbean Beach Resort Pirate Room Review called them the worst at Walt Disney World. This was for a number of reasons–they’re location far from everything else at Caribbean Beach Resort, the small size of beds, and thin mattresses that literally felt like sleeping on an uneven pile of plastic.

Over the years, we cautioned readers against accepting an “upgrade” to the Pirate Rooms. Even though these rooms had a higher rack rate, they would be a functional downgrade for most guests due to the aforementioned location and comfort level.

In fact, that’s why Walt Disney World converted this section of Caribbean Beach to Pirate Rooms in the first place: to make this remote area of the hotel more appealing, and convince guests to book it. When that didn’t work, Disney would overbook the rest of the resort and hand out free “upgrades” to the Pirate Rooms. It’s the equivalent of getting a free copy of the Cats DVD–sometimes nothing is better than something.

If that was the entirety of this saga, Walt Disney World’s decision to retire the Pirate Rooms at Caribbean Beach would make perfect sense. It would be an open and closed case of guest satisfaction. (And maybe it still is.)

However, in the time since the Pirate Rooms debuted, so too have the Skyliner and Spyglass Grill. The hub gondola station is directly across the water from the Trinidad section of Caribbean Beach where the Pirate Rooms are located, and they now have a convenient dining option in Spyglass Grill. These are excellent enhancements that truly elevate the Pirate Rooms.

On top of that, a soft goods refurbishment that wrapped up early last year brought thicker new mattresses to the rooms, and also refreshed other furnishings to improve the functionality of the rooms. We still heard complaints even after this refresh, but the rooms were much improved–to the point that I’d no longer decline the upgrade.

Now, it’s entirely possible that guest satisfaction was still too low for the Pirate Rooms. Maybe Walt Disney World is going back to the drawing board, and plans to come up with a new TBD themed concept for this area of CBR. Or, perhaps they’re just going to renovate these into regular rooms, realizing the other improvements mean the “crutch” of themed rooms is no longer necessary.

I’m going to put on my tinfoil hat and bet against all of that. Instead, my guess is that an entirely new hotel is coming to this plot of land. I have zero information, insight, or even rumors to support my theory. Rather, this is entirely out of left field speculation, based on…pretty much nothing at all. Let’s just call it a hunch.

This is largely predicated upon how Walt Disney World handled the announcement. There’s no banner up on the Caribbean Beach Resort page that mentions a refurbishment, which would necessarily be required if the Pirate Rooms are going to be discontinued (unless the plan is to let them sit empty).

Moreover, there’s not really any information at all–just a brief statement during a travel agent webcast meant to preemptively quell questions about why the Pirate Rooms are no longer bookable. And although that call indicated the Pirate Rooms would be discontinued in 2023, they are already unavailable to book for the remainder of this year, too.

It’s not just that they’re sold out for select dates with the message: “This room type is unavailable for the dates, party size or offer selected.” The Pirate Rooms are gone completely, no longer bookable even though they very much still exist (for now).

So something is up. Again, the most realistic possibility is that it’s time for Caribbean Beach to get another room reimagining. The last one was several years ago, and we’ve noticed many rooms are looking tired and a bit worse for wear. Maybe Walt Disney World is simply going to start with the Pirate Rooms and move on to other buildings from there. That’s probably a better theory–and with 99% less tin foil–than what I think is going to happen.

Another possibility is that Disney will continue to place guests in the Pirate Rooms, but without them booking the category. Given the complaints about Pirate Rooms over the years, that may not go well from a guest satisfaction standpoint.

My theory is that Walt Disney World has earmarked this site for its next resort expansion. That an announcement will come in the not-too-distant future, possibly at the D23 Expo in September. Shortly after that, the buildings of Trinidad will be razed.

Just think about it. This plot of land is conveniently located across from the main Skyliner station, could share infrastructure with an existing resort, and wouldn’t require a tremendous amount of redevelopment. It basically checks all of the boxes for Disney’s ideal expansion.

There’s also the reality that exactly this has been rumored before. Back between 2014 and 2016, credible sources indicated that a Disney Vacation Club add-on to Caribbean Beach Resort was in development, and likely to occupy either the Trinidad location or area across the water from it.

Of course, that project did end up coming to fruition, albeit on the other side of Caribbean Beach. In part of the area where the DVC add-on was originally rumored, the Skyliner hub station was built. Nevertheless, if DVC expansion was viable in this area back then, that would be just as true today.

It doesn’t even require rumors or a vivid imagination to envision this. Caribbean Beach is only a few years removed from exactly this happening with Disney’s Riviera Resort. That DVC resort replaced several guest room buildings at Caribbean Beach Resort, providing a cost-effective way of expanding Disney Vacation Club and consolidating CBR.

Pretty much the exact same scenario played out over at Disney’s Coronado Springs Resort. Gran Destino Tower was added there rather than on a standalone parcel to utilize existing infrastructure, keep costs manageable, and help “fix” that sprawling resort. The recent past is filled with examples of Disney adding on to existing resorts rather than building in fresh locations.

In fact, those examples are part of what gives me pause about the viability of this theory. Right now, Disney Vacation Club is in the process of expanding its portfolio at the Grand Floridian and Polynesian, and there are still a ton of unsold points at Disney’s Riviera Resort.

Even after those “low hanging fruit” projects are finished, it probably makes more sense to revisit the abandoned Reflections site, as prep work was already completed there. While that would be a standalone resort, its proximity to Magic Kingdom gives it a lot of appeal, especially with Wilderness Lodge seeing a spike in its popularity. All of that casts doubt on the timing for another DVC addition at Caribbean Beach.

Rather than more DVC, this could be another tower hotel a la Gran Destino.

This makes sense for similar reasons, minus the need to sell more points. Those who have followed the saga of unavailable resorts at Walt Disney World over the last year-plus might think this is a no-brainer. However, that lack of availability has come while not all hotels were open, and even those that were operating weren’t filling 100% of their rooms. Once occupancy rates normalize, it’s hard to say what the balance of supply and demand would be.

Ultimately, it’ll be interesting to see what happens with the Pirate Rooms at Disney’s Caribbean Beach Resort. As should be patently obvious from the rambling commentary, I have no clue whether there are bigger plans…or it’s just going to be a simple refurbishment to remove the swashbuckling soft goods.

Basically, this is just my way of going on record to guess that Walt Disney World has ambitious plans for this parcel. Maybe not this year or in 2023, but eventually my tinfoil theories will be vindicated. It might not be until 2055, but it will happen someday. With the monorail loop only able to sustain so much development, more will be built around the Skyliner in due time. Replacing the Trinidad buildings at Caribbean Beach with a tower makes too much sense for it to never happen.

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Are you disappointed that the Pirate Rooms at Disney’s Caribbean Beach Resort are being discontinued? Think this will be a garden variety room refurbishment, or something more? Does the nearby Skyliner hub change your perspective on the Trinidad section of CBR? Do you agree or disagree with my assessment that this real estate is too ‘prime’ to remain part of Caribbean Beach forever? Any questions we can help you answer? Hearing your feedback–even when you disagree with us–is both interesting to us and helpful to other readers, so please share your thoughts below in the comments!

47 Responses to “Dead Rooms Tell No Tales: Caribbean Beach Pirate Retirement”
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