The fact that the Disney Skyliner provides alternate transportation to Epcot and Hollywood Studios is only the second-best thing about it. Even better is that it connects four fun-to-explore Disney resorts, accessible via a semi-fast-moving gondola with lovely (if not a little scary) views and enough airflow that it’s not stifling.

On one of our days off, we kinda, sorta did a Disney Skyliner bar crawl — we hit up bars at 3 of the 4 stops but spent time at each resort nonetheless. We loved it, and it made for an excellent Disney date night.

P.S. Here’s the Disney Skyliner map if you want to see exactly where it goes.

First Stop: Disney Springs

We weren’t staying on property, so the first thing we did was drive to Disney Springs. (A bit later, I’ll explain why we didn’t drive right to a resort.)

Since we didn’t know how much food would be available at the Skyliner hotel bars or if we wanted to eat along the way, we had lunch at City Works.

A Quick Word About City Works at Disney Springs

We’ve eaten at City Works a number of times — we even have a pint glass that we bought as a souvenir.

Ironically, we don’t recommend this restaurant.

The reasons we’ve opted for it at times are:

• There’s almost always walk-up availability.
• They’re very flexible when it comes to reservations.
• The menu has a lot of items, so there’s probably a dish we’re in the mood for.
• It’s excellent if you want beer or cider flights.

In general, though, the mixed drinks taste cheap and the food’s just OK.

Exception: If what you’re after is a huge selection of beers and ciders, especially tasting flights you customize yourself, this place is where you want to go. We just suggest sharing an appetizer or skipping food here altogether and eating somewhere else.

Kicking Off the Disney Skyliner Bar Crawl at the Caribbean Beach Resort

We found our way to the bus depot at Disney Springs and stood on the Caribbean Beach line.

You don’t need to be staying on property to take the internal Disney busses. They don’t ask for proof of where you’re staying or anything like that. Plus, Disney wants you to explore the hotels so you get interested enough to stay there in the future.

Here’s Why We Didn’t Drive Straight to a Resort for the Disney Bar Crawl

Unless you’re a guest or have a restaurant reservation (and the security guard will check), most Disney resorts don’t let you park in the regular lot.

The one exception to this that we know of is the Polynesian. And we only know that because a security guard at another hotel, one we weren’t allowed to park at, told us. He suggested we try the Polynesian and say we’re going shopping.

It’s worked the two times we’ve tried it, once at Christmastime and once around Halloween.

(In case you’re wondering, we usually stop at the Kona Cafe coffee bar and get drinks and appetizers at the outdoor section of Trader Sam’s Grog Grotto. The Kalua Pork Tacos are so good we usually order a second dish, and I love the Tiki Tiki Tiki Tiki Tiki Rum. Mike’s a Zombie guy.)

Banana Cabana at Disney’s Caribbean Beach Resort

The Banana Cabana was as chill as they come. Our server was cool and relaxed, the vibe was colorful and island-y, and the drinks were good. I can’t remember what I ordered, but if I know myself, it was the Caribbean Mai Tai. We were off to a great start.

We popped into Calypso Trading Post, the hotel gift shop, and bought … something. No idea what it was. A keychain? Maybe a keychain.

Next, we walked around. A lot. Caribbean Beach is a huge resort. Walking from one end to the other is no joke, and we didn’t know where we were going, so we got turned around once or twice on our way to the Skyliner boarding.

It’s adorable though. So, so cute. You really feel your shoulders relax — you’re on a real vacation here. I’m also partial to this hotel because it’s where I stayed with my family a few times as a kid.

Skyliner to Pop Century

Eventually, we found our way to the Skyliner and hopped on. This was our first time on it, and we loved it.

For anyone who remembers the Skyway at Walt Disney World, this feels like a nod to it. It’s a different design and you’re not traveling over a park, but it’s still sprinkled with Disney magic. I was happy to be up in the air again.

We walked around Pop Century quite a bit, because everywhere we went, I stopped to screech, “That is so cute!” over and over.

I’m not a fan of staying at the more budget-friendly resorts, but boy are they themed out in the best way.

Everything at Pop Century is clever. It reminds me of being at Toy Story Land in Hollywood Studios — you can look and look and look, but you’re going to miss some creative design detail, even if it’s 3 stories tall and right in front of you.

We went to Petals Pool Bar and ordered Sunshine Margaritas. They weren’t great. This feels like a place where you should be walking around with a colorful cocktail in your hand, but it didn’t taste so good.

Short Walk to Art of Animation

For the next stage of the Disney resort bar crawl, we walked over to Art of Animation, which is right next to Pop Century. At one point, they either were or had planned to be one big hotel, and they’re still situated conveniently to one another.

We had just downed our strong cocktails by the pool bar, so we skipped having a drink here. Instead, I oohed and aahed at the Finding Nemo theme, and then we went to the Ink and Paint gift shop and bought a puzzle.

Ending the Disney Skyliner Bar Crawl at the Riviera Resort

We boarded the Skyliner and rode it to the Riviera. We saved this one for last because it’s the most sophisticated, and we thought capping off the evening here once the sun had gone down would be a nice ending.

We learned we’re not big fans of the Riviera.

It’s a lovely hotel — the look of it is undeniably nice. And every time I see it on a YouTube video, I go, “Where is that?!” and then have to remind myself that I’ve been there. Also, the Peter Pan mosaic in the entryway is heavenly.

That said, this just isn’t the place for us.

That’s not that rare. I’ve stayed at a number of Disney hotels, and sometimes you simply don’t click with one. In my experience, that has to do with personal preference more than the hotel being “wrong” in some way.

Mike isn’t crazy about the Contemporary; I have a soft spot in my heart for it. I stayed at Port Orleans Riverside and wasn’t impressed, but I have a friend who loves it.

We may also not be Riviera fans because we had quite a crummy experience at Bar Riva. It took forever for our server to come over, and then we waited twice as long for our food, which was, like, one appetizer.

Bus to Disney Springs

We were ready to be back at Disney Springs by this point. The Skyliner pub crawl was over, and it’s surprisingly tiring to do that much hotel hopping in one day.

Back at Disney Springs, we did a bit of shopping in the stores we don’t usually go into, in the Town Center section. Lovepop completely won me over, and we bought a tiny vase at Sugarboo and Co. (not a candy store, believe it or not).

Then we went to Goofy’s Candy Company (we rarely leave Disney Springs without a stop here), followed by the Marketplace Co-op (souvenirs you won’t find anywhere else) and had dinner at The Boathouse.

Disney Skyliner Bar Crawl: Worth It?

Was the Disney resort bar crawl via the Skyliner worth the half a day it took to go to all four resorts? I think so. More for the experience than the drinks, though.

The Skyliner is fun to ride, period, Disney bar crawl or no Disney bar crawl. And since it’s free, if you have a spare day, why not?

Caribbean Beach’s Banana Cabana was the highlight of our day as far as ambience and drinks went — thumbs up for both. Pop Century and Art of Animation are full of pageantry, but the margarita we had was hard to get down. And we didn’t love Riviera, but it has a solid reputation, so our experience may have been a one-off.

If you’ve never been to these resorts, do the Disney Skyliner bar crawl — actual bars and drinking optional

If you’re after a true Disney World bar crawl experience, yummy drinks included, maybe stick to Disney Springs or save it for a World Showcase day. You’ll have more options and the drinks will be better.

Make your trip to Walt Disney World way more convenient by packing these items — they made our Airbnb feel more like home during our month-long WDW vacation.