Disney World Skyliner Opening Trip Report Part 1

Welcome to our trip report covering the opening of the Disney Skyliner in Walt Disney World! The primary purpose of trip reports is to supplement our existing content to let you know how our strategies are actually working at a given time! This post introduces the trip report and covers booking the trip, our arrival into Orlando, and our Pirate Room at Caribbean Beach!

disney world skyliner view 01.jpg

About This Trip Report

This trip report covers a short, three-night visit to Walt Disney World for the opening of the Disney Skyliner gondola system, along with some other highlights, including the end of IllumiNations and the start of Epcot Forever, the new nighttime show at Epcot. We’ll also be checking in on Extra Extra Magic Hours at Hollywood Studios.

This trip takes place during the daily Extra Magic Hours period at the resort, which has about a month to go, ending November 2. These posts cover the August 29 to November 2 highlights at Walt Disney World (new tabs):

After November 2, things will stabilize a bit at the resort, though holiday crowds promise to pose their usual challenges. And then December 5 will arrive and we’ll be faced with a new set of challenges—this time just at Hollywood Studios—posed by the opening of Rise of the Resistance.

Booking This Trip

While the Skyliner’s debut is certainly a gamechanger at Walt Disney World, it was the ending of IllumiNations on September 30 that motivated us to book this trip. As longtime fans of the show, we just couldn’t pass up the chance to give it a proper goodbye.

disney world skyliner trip report 01 illuminations.jpeg

As always, I emailed Lauren Quirk, our go-to travel agent for Disney trips. I can’t recall exactly what motivated me, but the best option wound up being a Pirate Room at Disney’s Caribbean Beach Resort. Caribbean Beach is the hub of the Skyliner, and we’d never stayed in the pirate rooms before, so this was a natural fit.

The room had an annual passholder rate available, so after 25% off we wound up paying $802.43 or $267.48 per night for the stay.

Originally when we booked this trip we had no plans for night one, though we later added Mickey’s Not So Scary Halloween Party. Our booked flight should work out fine for that, with a scheduled arrival of 11:44AM.

Our round-trip fare for two on Frontier came out to $193.92. As always, we’re happy to fly low-cost with each of us only having a personal item.

As we have Walt Disney World annual passes, we didn’t need ticket purchases. So the cost of this trip comes out to $996.35. We do have a guide to buying Discount Disney World tickets, for those of you interested. (The total cost doesn’t include party tickets, those were reassigned from when our last trip was cut short by Hurricane Dorian.)

Lessons About “Cheap” Flights

Most of the time I breeze through our travel days because they don’t contain much interesting. But today our travel morning actually has some interesting lessons.

disney world skyliner trip report 04 flying.jpeg

Let’s start with our “cheap” morning flight. Because we're fortunate to live in downtown Chicago, we can really fly out of O'Hare at any hour and take a bus and train to the airport for $2.50 each.

The trip takes about an hour, and with TSA PreCheck and never any checked baggage, even a 6AM flight isn’t the worst thing for us (it also gets us to our destination earlier, which is great).

As a result, I’ll book pretty much any early time at a low price. So I did that for this trip, booking a Frontier flight that had a “door close” (boarding ends) time of 7:45AM. Turns out this wouldn’t work out well.

First of all, Frontier now flies out of O’Hare Terminal 5, which requires an extra shuttle bus to get to (it’s usually a tram, but construction is ongoing at O’Hare). Second, the train to the airport was undergoing construction—so another shuttle bus required.

Since we didn’t know how much these shuttles would impact us, the safest option was just to take an Uber. At 6AM, this cost us $85. It basically means any savings I made booking the two of us on a cheaper flight were wiped by the cost of the inconvenient time.

disney world skyliner trip report 03 flying.jpeg

This is a good reminder that your “cheap” flight might not always be so cheap. Increased transit or parking costs, in particular, are a common issue in this regards. (While I could have foreseen the Terminal 5 issue, I didn’t know in advance the train to the airport would go down, to be fair.)

One other common issue—not present here—is whether you’re just paying for an extra hotel night. A flight that lands at 2AM might be cheap, but the hotel you have to check into for an extra 3 hours of sleep could negate those savings. Keep these things in mind when shopping for flights.

Luckily, our driver declined a cash tip (I always offer hefty cash tips to keep my Uber rating up) for the long, surge priced journey.

We timed our arrival perfectly and, after a slow TSA PreCheck experience (yuck Terminal 5), we walked right onto the Frontier flight. I love Frontier, but their move to O’Hare Terminal 5 is a problem for me.

The only thing I’ll say about the flight is that Frontier claims to be “America’s Greenest Airline” but serves their coffee with two coffee cups and a lid, and their creamer comes in a packet in a plastic cup with a stir stick. If nothing else, it’s a poor display given the state of “green” culture.

disney world skyliner trip report 02 flying.jpeg

Magical Express and Crowds

Landing at MCO on time, we arrived at Disney Magical Express Check in at 11:39AM. It was there we found crowds.

I’d seen on social media that this weekend had been crowded at Walt Disney World. Lots of people seemed to think this was just the end of the ongoing “low” crowds. Well, by the end of the weekend things were back to “low,” so why the crowds this weekend?

I think it was mostly Rosh Hashanah. The holiday was Sunday/Monday, and many schools had the Monday off. Multiple followers from New York (not sure where) reported schools having Monday off, for example.

What’s notable is most crowd calendars didn’t account for the holiday. We discuss this is our post discussing Disney crowd calendars, but there are just so many blindspots in crowd calendars.

disney world skyliner trip report 05 dme crowds.jpeg

With changes happening frequently at Walt Disney World, and with guests more able than ever to research and plan a quick visit on short notice, I’m growing less and less confident crowds will be predictable outside of major holidays going forward. Always plan for high crowds and bask in the greatness of low crowds when you get them.

After a decent wait, we boarded the Magical Express bus at 12:20PM and were at the hotel at 12:57PM (we were the only stop). I had checked in via the app, and our room was available, so we walked right there, arriving at 1:07PM.

I’ll cover the room quickly below, but I want to jump ahead and say that after a 20 minute break to change (and photograph the room), we caught the next bus to Animal Kingdom, arriving at 1:59PM. That’s 2 hours, 20 minutes from Magical Express check in to our first park.

Our Pirate Room at Caribbean Beach

Having checked in via the app after landing at MCO, I got a text while we were on the way that our room was ready. This meant we could skip the front desk and go straight to the room.

This section isn’t a full review of the room, but I’m going to give a quick gallery of photos and then briefly discuss my impressions:

Like the Royal Rooms at Port Orleans Riverside (which seem the most natural comparison), the Pirate Rooms are themed at pretty much every corner. This means the fixtures, drawers, bed frames, and mostly everything else are themed.

While I think the Royal Rooms have more of a “wow” factor, I was also surprised at how much they’ve worn. Part of the reason the pirate rooms work is because while they might be worn around the edges, the wear fits the theming (in an aesthetic sense—obviously poor functionality is never okay).

Coming In Part 2…Goodbyes at Animal Kingdom and Magic Kingdom

All Your Other Disney World Planning Questions Answered

Don't be overwhelmed by Disney World planning! Take a second to check out our most important content and you'll not only be an expert, but you'll save big $$$ along the way.

Just starting out? Check out our Walt Disney World planning guide! If you're still picking dates, we've got everything you need to know about Disney crowd calendars. For picking your hotel, check out our Walt Disney World hotels guide.

When it comes time to book we’ll help you find discount Disney World tickets. Decide whether you need a dining plan in our Complete Guide to Disney World Dining Plans! And at 180 days out it's time to book those Disney World Advance Dining Reservations!

Don't forget to master your Disney World FastPass+ strategy a few months in advance. We'll keep you out of long lines so you can maximize the magical time in the parks! We've got park-specific guides as well: Magic Kingdom FastPass, Epcot FastPass, Animal Kingdom FastPass, and Hollywood Studios FastPass.

Know what to ride with our guides to: Magic Kingdom rides, Hollywood Studios rides, Epcot rides, and Animal Kingdom rides! Plus learn about the water parks with our guide to Blizzard Beach and our guide to Typhoon Lagoon! And for some some fun prep, check out our Ranking of Every Ride at Walt Disney World.

Finally, before you head out, be sure to check out our to-the-point packing list, 10 essentials you forget to pack for every Disney trip. And if you're interested in saving, there's no better list than our 53 Ways to Save on your Disney trip from start to finish.