Highway in the Sky Dine Around at Walt Disney World: A Review

Highway in the Sky Dine Around

A Review of the Highway in the Sky Dine Around at Walt Disney World

Disney’s Highway In The Sky Dine Around is intended to be an upscale Walt Disney World version of a pub crawl (my description, not theirs). This VIP Signature Dining experience takes you on a whirlwind journey around the Deluxe Resorts serviced by the Walt Disney World Resort Monorail on Seven Seas Lagoon in the Magic Kingdom Resort area.

Your journey covers three Deluxe Disney resort hotels and takes place over roughly four hours — culminating with a viewing of the the Happily Ever Fireworks that take place in Disney’s Magic Kingdom Park (although you watch the show from Disney’s Contemporary Resort).

Each stop on the Dine Around is roughly 30 minutes in length and some resorts have more than one stop (so two different locations within the hotel).

As a lifetime luxury Disney traveler, I always try to take a glass-half-full approach to Disney experiences. In this case, however, while the concept of the Dine Around is great, the implementation is unfortunately not quite up to par at this time.

The Four Monorail Stops of the Highway in the Sky Dine Around

Here is how the Highway In The Sky Dine Around unfolded for us, along with my thoughts on this VIP Signature experience.

Spicy Tequila cocktail at The Wave

Your first cocktail of the evening is a spicy tequila infused concoction served in the waiting area (the Blue Room) at The Wave in Disney’s Contemporary Resort.


First Stop: The Wave at Disney’s Contemporary Resort

Our journey began at The Wave in Disney’s Contemporary Resort. The Wave is located on the main floor, right next to the hotel’s front desk check-in area. This is where all Dine Around guests will meet at 5:30 p.m. to check in with your hosts for the evening. You will be given a name tag and a VIP pass, which is important because that is what allows you to take advantage of express access to the monorail for the length of the event (bypassing security at most stations).

Guests meet in the lounge to the right of the main reception desk at The Wave (look for the signage). This is sometimes called The Blue Room. At this first stop you will be welcomed, given your instructions for the evening (you’ll supposedly be given five minutes notice at each stop before moving on to the next — more on that later), and then you begin with your first round of food and drink.

We were treated to a spicy tequila cocktail, which was good and tasty and enjoyed by most guests (tequila is not my thing, so I passed on this one after trying a sip of it). Following the cocktail you are then treated to a small shooter of a tomatillo-based soup — which is excellent. The soup was a big hit with all 25 guests in our group.

From there we were given our five minutes’ notice and then whisked off to the monorail to make our way to our next stop.

Polynesian Resort Dine Around

Your high-top table at Disney’s Polynesian Village Resort.


Second Stop: Disney’s Polynesian Village Resort

The second stop is at Disney’s Polynesian Village Resort.

Here you basically gather in a makeshift location just inside the main lobby to the right of the monorail access doors. There are two lounges at this resort, so this choice is rather puzzling and it was a letdown for me. They do a decent job of making it look nice, but it’s really just a group of tables set up in the lobby, in the spot that previously held a Disney Pins kiosk and some other retail gift racks. It is not very impressive at all. The area is mainly high-top tables and standing-room-only.

You will get a Hawaiian lei and be treated to some live ukulele music while you sip on a mai tai and dine on a small trio of food prepared at Kona Cafe. There is a beef dish, a fish dish and a ceviche. Once again, the food and drink (and the entertainment) is good (although we couldn’t really hear the ukulele player from the back table). They even supplied our young daughter with a virgin pina colada. However, the stop is overshadowed by the poor choice of location. The area is hastily constructed and is basically a hallway cordoned off with some rope. Not very special at all and you will get no sense of this resort if you have never visited before. So bear that in mind.

After our five minute warning and a very hurried restroom break for some, we boarded the monorail (the group has one reserved car at the front of the train) and headed off to our next stop on the tour.

Dine Around Dinner at Citricos

Your dinner plate at Citricos.


Third Stop: Disney’s Grand Floridian Resort and Spa

The third stop takes place at Disney’s Grand Floridian Resort and Spa and there are actually two locations (two stops) on the tour here. This is where the wheels really fell off the wagon for our group. I didn’t think it was possible to make the Grand Floridian (my favourite Disney Resort) experience seem average, but the Highway In The Sky Dine Around managed to do just that.

The first stop is Citricos, one of the three Signature Dining Restaurants at Disney’s Grand Floridian Resort. You will have a light and quick dinner here, accompanied by a glass of red or white wine. Dinner is a sampler plate with fish and beef, along with bread on the table. Once again the food and drink is pretty good, however, not all went smoothly. This is where our group ran into some problems and where we noticed that the Highway in the Sky Dine Around could be much better organized.

Our group of guests was divided into three tables in the restaurant (assigned by our hosts). The problem arose when, after finishing our meal, we noticed that the other two tables were no longer in the restaurant. They had left without us. None of the three Dine Around hosts had approached our table to give any warning (as they had at the previous two stops). We called our Citricos server over and he seemed as confused as we were. We were not given any notice by anyone and the rest of the Dine Around group (including all three Disney hosts) had moved on without us. I have been on most Disney VIP experiences and the Cast Members are usually excellent at taking head counts when moving from place to place. This is not the case with the Highway in the Sky Dine Around.

Charcuterie, Garden View Tea Room, Disney's Grand Floridian

The charcuterie plate to be shared by three guests at the Garden View Tea Room, Disney’s Grand Floridian Resort.


It was a bit of hassle to fend for ourselves to find out where they had gone. We knew that there were two stops here and when our server told us that he thought they may have gone downstairs, I had a pretty good idea that the next stop was the Garden View room. Turns out that they had indeed moved on to the second location at the Grand Floridian, which is the Garden View Tea Room on the main floor. We made our way there on our own and expressed our dissatisfaction to our hosts about being forgotten and left behind. We received no apologies of any kind, which was a surprise and a disappointment. For a Signature event such as this that has been running for many months now, I would have expected much more. There are three hosts on the Dine Around, so there’s not much of an excuse to forget an entire table of guests and then offer no apology or commentary at all. So this was a big detractor for me and is very un-Disney-like in my 47+ years of Walt Disney World experience.

In the Garden View Tea Room we joined the rest of our group, already well into their course. Here you are treated to a plate of cheese and charcuterie, accompanied by a glass of sparkling wine, champagne style. The Garden View room was half empty and this part of the tour was not a very magical experience because it felt a little like we were eating in an area that was an after thought (yet again). It was dark and our group was shoved over on one side of the room, with a large dark and barren space beside us. After a short time (for our table) we were given our five minute notice and then we headed back upstairs to the monorail to make our way to our final stop.

Highway in The Sky Fireworks

Closing out the night with fireworks from the viewing deck at Disney’s Contemporary Resort.


Fourth Stop: Disney’s Contemporary Resort

The final stop on the tour is desserts, liqueurs and coffee at Disney’s Contemporary Resort. This takes place in an outdoor reserved seating area on the fourth floor of the hotel to watch the Happily Ever After Fireworks in Disney’s Magic Kingdom Park.

This is a nice stop where you are given a hot coffee and a choice of three liqueurs (Bailey’s, Khalua or Frangelico). Plus there are three small dessert options from which you can choose to enjoy while watching the fireworks on the outdoor patio. There is some seating (it’s the permanent seating in that area, but not enough for all) along with a few high top tables that they set up for the event.

After the fireworks, the Dine Around ends and you are given a small box with two truffles as a parting gift when you leave the event.

Even though the recommended age is 12 years old, our nine-year-old daughter was allowed to take part with us. Just be sure that your kids are well behaved as this is primarily an adult-oriented event (our daughter was the only young person in our group).

My Thoughts on the Highway In The Sky Dine Around

It has potential…with a few adjustments

If you read my blog on a regular basis, you know that I am a big fan of luxury Disney experiences and I always try to find the best in them. The truth is that most of the VIP experiences are things that I really enjoy and I have not found one that I would not highly recommend…until now.

Unfortunately, The Highway in the Sky Dine Around is not on my list of recommended Disney experiences in its current format. However, the issues that we experienced are fixable, in my opinion.

Here are the areas that I would recommend need to be addressed to make the Highway In The Sky Dine Around a better event:

  • Hosts should always ensure that everyone is accounted for and it should be less rushed. Dropping the second stop at Disney’s Grand Floridian Resort might be one way to gain back some time. The way that the Garden View room is used on the Dine Around is not flattering to the room itself, nor is it comfortable for the guests. The charcuterie could easily be served in Citricos after the meal portion.
  • Most of the tour feels like it takes place in temporary or makeshift locations. With the exception of the dinner portion of the Dine Around at Citricos, the rest of the Dine Around takes place in what feels like nooks and crannies of the resorts where they could squeeze in a group of people. Even the portion in the Garden View Tea Room at Disney’s Grand Floridian Resort left something to be desired. The room was dark and half empty — only a shell of what it can be at excellent events such as Disney’s Perfectly Princess Tea, which also takes place there. Moving guests to a darkened half empty room felt exceedingly underwhelming. For the price you pay for this event, guests deserve much better. The Dine Around would be much more enjoyable if it were held in the Outer Rim at Disney’s Contemporary Resort, Trader Sam’s Grog Grotto at Disney’s Polynesian Village Resort and Mizner’s Lounge at Disney’s Grand Floridian Resort and Spa.
  • Since the event is so rushed, there is barely enough time for bathroom breaks for some guests. For an event that revolves around cocktails, this is not a good thing. Longer stops will allow for more time.
  • Finally, the fact that an entire table was forgotten and left to fend for ourselves was also not a good sign and soured the evening for our entire table. Again, not very well organized as none of our guides (three of them) nor the servers at Citricos thought to alert us that the rest of our group had departed to their next station. Headcounts of guests should be a standard operating procedure at each stop.
Highway In The Sky Dine Around, Polynesian Monorail Stop.

Our monorail prepares to depart Disney’s Polynesian Village Resort as the sun sets on the Highway In The Sky Dine Around.


The Good Things about the Highway In The Sky Dine Around

On a positive note, the food and drinks were excellent at all stops, so that is a big plus. Also, the hotel hosts who speak at each stop on the tour are very gracious and do an excellent job providing information on the properties and the food and drink (although you can tell that they are pressed for time, which is an overriding problem with this event).

My general view on the Highway In The Sky Dine Around is that if you are new to Walt Disney World Resort, this could be a good way to take a whirlwind tour of these three amazing Deluxe Disney Resorts and enjoy some top notch food and drink along the way. Plus, you’ll meet some very nice people within your group as you mix and mingle your way around the monorail line. However, I would not recommend this VIP experience unless the issues are addressed to make the Highway In The Sky Dine Around into the premium experience that it really deserves to be.

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As a Luxury Travel Blogger and author of The Very Best of Walt Disney World Resort, I blog regularly about Disney vacations of all shapes and sizes.

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Mike Belobradic: The Finer Side of Disney Travel
Luxury Travel Blogger – Deluxe Disney Travel Specialist
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