Highway In The Sky Dine-Around: A Memorable Monorail Meal

Last week, Disney announced a new upscale special dining event modeled after the popular “monorail crawl” many Disney fans love, called the Highway In The Sky Dine-Around progressive dinner. Offered Tuesdays, Fridays, and Saturdays (with a short break for the holiday season), this event highlights dining offerings at Disney’s Contemporary, Polynesian Village, and Grand Floridian Resorts in a four hour experience priced at $150 plus tax per person (gratuity included, no discounts of any kind offered).

I was lucky enough to book a spot for the first night of this event last Friday on a whim. As it turns out, there really was a bit of luck involved here, as the event is already nearly sold out through the initial booking period currently running through March 2017 (sporadic parties of 1 and 2 are available on select dates as of the date of this article)! Here, I’ll walk you through the logistics and food/beverage I enjoyed during the event, which I’m sure will change over time as this event settles into permanent status, but it will give you a good idea of how it all works and whether it would fit your dining preferences.

Booking and Arrival

First, a few notes about booking: Many guests attending Friday’s dinner noted that some Cast Members assisting in booking by phone had no clue what the event was (which can sometimes happen with new events). I was able to book online directly through the Disney site without hassle (by searching for the Highway in the Sky event page). On Thursday, I received a call from a Cast Member confirming my attendance and checking if I had any food allergies or accessibility concerns, as the event includes a set menu and several sets of stairs and standing throughout. I was also reminded that valet parking was included at the Contemporary Resort. All of these items were touches I’d expect of any upscale dining experience, so I was happy to see they hadn’t been lost in the shuffle of it being a new event.

I was told to check in to the podium at The Wave… restaurant around 6:30 PM (event start times will vary based on the time of Magic Kingdom’s fireworks on any given night). Several Cast Members were around to welcome me, and once all the business was settled, I was led into the lounge area in The Wave’s lobby, where one of the blue alien-spaceshippy trippy rooms had been reserved for our group. If you’re acquainted with these lounge areas, you’ll know they aren’t particularly huge, so I was curious to see how big our dining party would actually be. As everyone filtered in, the group grew to about 25 guests – a reasonable size that seemed intimate but not so small that you couldn’t socialize with lots of different people.

Stop 1: The Wave… Of American Flavors

As soon as I found a seat next to some new friends, a server promptly handed me a Bay Lake Sunset, a drink you’ll be familiar with if you’ve ever gotten the chance to visit Bay Lake Tower’s Top of the World Lounge. The Bay Lake Sunset is, to be blunt, a bit too sweet for me, but it’s a fun and beautiful drink properly themed for an evening on the monorail loop. Vanilla vodka and rum form the liquor base of this drink, with pineapple juice and grenadine stratifying to create a “sunset” effect in the glass (perfect for photos, but to me, not terribly tasty when you get a sip just of sickly-sweet grenadine).

Shortly after everyone arrived, managers from The Wave welcome us and introduced the Convention Guest Services guides who would lead us around for the evening. Chef Baker then introduced the first bite of our dinner:

butternut squash bisque, topped with granny smith apple verjus and crispy salsify, with a truffle oil/pumpkin brittle garnish. For such a small bite, there was a lot involved here – the bisque was creamy and rich, a touch of salt offsetting the sweet squash flavor. Diced apples poached in vinegar introduced a slightly acidic and sweet counterpoint to the rich soup, with the crispy salsify (a root vegetable that looks like a white carrot) adding texture to the mix. The truffle oil along the rim overwhelmed a little of the natural sweetness in the soup, but the crunchy pumpkin brittle added an additional earthy note to cap off the bite. This was a seasonally appropriate and tasty start to our meal.

As would become the trend throughout the night, we were given a 5-10 minute warning before we needed to be in place to depart for our next location, at which point we could use the restrooms or finish up our food and drinks. This reminder was helpful, as I never felt like I had to pay attention to the time or feel like I’d be left behind if I needed to duck out quickly. As the night progressed, I never felt rushed by the pace of the event, but always had to be mindful that my time in each dining venue was limited, so as not to linger too long over one bite.

Stop 2: Trader Sam’s Tiki Terrace

We exited The Wave lounge around 7:15 PM and made our way through a few back doors and stairwells up to the Contemporary’s monorail platform, where we walked straight onto an empty car in a waiting monorail. This was, to put it plainly, a little awkward, considering a rather large crowd of guests waiting to board the monorail watched this happen – this would become a theme of the night. Personally, I felt a bit uncomfortable with the reserved monorail car and that everyone was waiting on us, but I also understand that logistically, that was what I’d signed up for.

In talking to a few of the Cast Members involved in leading us around, this was the best possible solution to reduce the awkwardness for all in each of the scenarios they’d tested in weeks leading up to the event.

By 7:30 PM, we’d reached the Polynesian Village Resort, where we were greeted by another manager and led down to the outdoor patio area known as Trader Sam’s Tiki Terrace. Our group occupied the “surfboard table” area against the building nearest the bar’s service window, with a few standing tables already set with silverware and chopsticks for our incoming appetizers. But first, libations! I was pretty surprised that our first stop included a full size cocktail, but even more surprised when this stop at Trader Sam’s included a full size HippopotoMai-Tai, one of the bar’s strongest drinks, packing a punch with two kinds of rum, curacao, orgeat, and fresh lime. Skippers from Trader Sam’s introduced the popular drink to us, though it seemed like many of the dinner guests were well acquainted (and happy to partake).

I’m a fan of this drink generally, and out of all of Sam’s drinks, this seems like the best choice when it comes to pairing alongside food, as it isn’t overly sweet or strong in any one flavor.

Our first two bites here arrived together – a piece of seared ahi tuna served on cucumber alongside a roasted beet “salad” with goat cheese and pistachio crumble. Even the seafood-averse diners in the crowd enjoyed the ahi, a lightly-seared selection with nutty sesame seeds grounding its fattiness, sweet cucumber providing a bit of crunch. The “salad” was one slice of golden beet, which came with a slightly-too-small dollop of goat cheese and a few bits of crunchy pistachio. Neither of these selections was more than one bite (or particularly revolutionary), which, at the time, felt a bit too small, but understanding we had to pace ourselves, I forgave.

Chefs delivered our final bite for this stop – a togarashi-dusted pork belly slice served with pickled vegetables. The veggies were nothing you couldn’t find on Trader Sam’s bahn mi, but the pork belly was divine – slightly spicy from the togarashi seasoning, sweet and rich from the natural flavors. Topped with a bit of aioli, it was even more over-the-top than I could’ve expected. We even stopped the chef who had prepared the dish to find out where we could try a larger portion (answer: the recently updated menu for the concierge lounge at Polynesian Village Resort features this bite on a rotating basis!).

Stop 3: Citricos

Shortly after 8:00 PM, we made our way up to the Polynesian’s monorail platform, where we encountered our only transportation delay of the evening. Even “VIP status” can’t avoid monorail delays at one of the busiest transfer times of the day (especially as this happened to be a Mickey’s Very Merry Christmas Party evening). Our chariot eventually arrived, and we were whisked off to the Grand Floridian, arriving at Citricos restaurant around 8:30 PM. Here, unlike our previous stops, our group was split into smaller tables and seated throughout the restaurant. One large group of 10 sat together, while the rest of us were grouped into parties of 4 or 5 and placed at smaller tables. I’m sure that party sizes will vary by evening and what is available at Citricos, but this was a nice opportunity to swap dining companions if you so chose, or get away from the larger group if that was more your speed.

Servers at Citricos gave us the option of a 5oz pour of a pre-selected red or white wine (or a flight of both), to pair with our incoming entrée, a duo of some of Citricos’ greatest hits: short ribs over mashed potatoes topped with a bordelaise sauce, and pan-seared scallops with roasted cauliflower topped with a parmesan nage (broth). This was really one of the only times during the night that I had to make a decision; even then, I hedged my bets and went with the flight of both wines. This turned out to be a smart decision, as both complimented each aspect of the duo entrée pretty well.

The scallops were perfectly seared with simple roasted cauliflower on the side (though I felt they could’ve used a bit more punch in flavor), and a spinach-tinted parmesan broth added a touch of salt to an otherwise light and mild dish. In contrast, the short ribs were decadent and rich, braised for hours and served over silky mashed potatoes (that again, I wish had been a bit more enhanced by another flavor). The star of both sides of the dish, to me, though, was the bordelaise sauce – red wine and bone marrow married with aromatics like shallots and a rich demi-glace stock base to enrich all the savoriness at the core of the beef and offer a bit of sweetness to the palate. In previous visits to Citricos, their ability to transform pedestrian plates to memorable meals has come with the swipe of a single sauce, and this dish was no different – it really elevated everything on the plate.

Stop 4: Garden View Champagne & Wine Lounge

We departed Citricos by 9:15 PM to head downstairs to the newly-crowned Champagne & Wine Lounge occupying the Garden View Tea Room during evening hours. Here, we enjoyed an after-dinner cheese and champagne course, featuring the ever-popular Iron Horse Fairy Tale Cuvee and a cheese board. By this point, many in the group had slowed down on eating, but I can’t say no to a few bites of cheese, so I had to take one for the team here and give it all a shot.

Each table split a few cheese boards during this course (the only sharing we had to do all evening), featuring goat, brie, cheddar, and blue selections paired with fresh honey, figs, and a black pepper sweet bread. This board is comparable to any you’d find on menus at signature restaurants like Citricos, Artist Point, or Flying Fish, and alongside the bubbly sparkling wine, was a welcome sight at the end of our meal. Servers gladly refilled our champagne glasses upon request, and also offered alternatives, just as we’d had at previous stops.

Stop 5: Disney’s Contemporary Resort

After we finished our last sips of champagne and taken a group photo in front of the Grand Floridian’s Christmas tree, we were whisked back upstairs to the monorail platform around 9:45 PM to depart for our final stop back at the Contemporary Resort for dessert and fireworks viewing. Once again taking advantage of a few stairwells, we walked directly from our final private monorail car of the evening straight to the fourth floor observation deck, where a small dessert buffet awaited, alongside coffee, hot tea, hot chocolate, and several cordials. The observation deck, a typically popular spot for free fireworks viewing, especially on event party nights during Halloween and Holiday seasons, had been roped off in one corner just for us, another awkward sight as onlookers watched us gather drinks and desserts just before the show began.

Because of the time of year and day that I attended the event, I was treated to a viewing of Holiday Wishes during our desserts. Most events will feature the regular Wishes show, but I will say, if you have the chance to book on a party night, it’s worth a shot. The view from this deck has always been one of my favorites for special party fireworks, and having a warm cup of coffee or hot chocolate (with a shot of whiskey or peppermint schnapps in it) while watching is really a treat. Going forward, the event’s start time varies based on when Wishes occurs that particular day, but keep in mind that weather and transportation are out of their control, so it may happen that viewing a full fireworks show isn’t in the cards for you – don’t plan this as your only fireworks viewing of a trip, but certainly enjoy it if it is!

The small assortment of desserts seemed fitting after the large meal we’d had – many guests didn’t sample anything or only tried one bite. Mini versions of the popular seasonal fruit tarts (complete with cream filling) and a few varieties of macarons were on offer, but the flourless chocolate cake and blood orange cake were unique treats I had to taste. Both desserts were rich but small enough that I wasn’t overwhelmed. The chocolate cake was dense and deep in flavor, but my favorite was the blood orange – light vanilla sponge and tart orange cream layers alternated in a pretty and delicious final bite of the evening. Cast Members allowed us to finish our desserts and say our goodbyes to fellow diners; by 11:00 PM, I was on my way home after a great meal (with a parting gift of artisan chocolate truffles in hand).

After-Dinner Musings

Ultimately, I left the meal quite satiated and happy I’d attended, which I’d say is a mark of a successful event. Though I’d visited each stop on the tour previously in my own dining adventures, I felt like every attempt was made to highlight the best parts of every location we visited. If you’ve never visited Top of the World Lounge, Trader Sam’s, or Citricos, the offerings we sampled were fairly representative of items you can order at each of them. Nothing was downsized or drastically reduced in quality just because we were a part of a special event, which I think is the best way to honestly represent the dining options available on the monorail loop.

In some respects, this progressive dinner reminded me of the now-sadly-defunct (or at least far less frequent) Tables In Wonderland monthly dinners, where you often come to the event with one friend and leave with several more, with socialization encouraged through different table arrangements. Though not advertised or planned, chef-guest interaction was also a highlight at several of the early stops during the progressive dinner, with each chef very willing to stop and chat about their dish with any and all guests. I hope that on future Highway In The Sky events, this continues; perhaps it could even expand to include Citricos, where a chef did not greet us, though that is complicated by the restaurant being very busy for normal operations by the time the tour arrives.

Meal Math

So, is this event for you? Well, the price tag is definitely high, and will be a deterrent for most. Before attending the dinner, I tallied up whether I felt the offerings listed in the initial released information would be worth the hefty price for me, and I didn’t feel they quite met the final bill, but I was still curious enough to book it. After attending and seeing what was on offer, I have a bit of a better idea how to quantify each aspect based on what we actually got to try. Here’s my best estimation of the value of each sip/bite, based on current prices:

1. The Wave: Bay Lake Sunset (varies, but around $11), butternut squash bisque (small appetizer, $6)
2. Trader Sam’s: HippopotoMai-Tai ($11), appetizer sampler (large appetizer, $13)
3. Citricos: standard glass of wine ($10), duo entrée ($42, average of both entrée components)
4. Garden View: Iron Horse Fairy Tale Cuvee ($15), cheese board ($16)
5. Dessert: cordial & coffee ($10), dessert assortment ($8)

Total: $142

Assuming you’ve made an attempt to finish everything served at the event by the end of the night, then, the $150 price tag no longer seems all that unreasonable. That being said, it would’ve been nearly impossible to do so unless you’d been training for a meal that filling, complete with five full-size-and-strength alcoholic beverages. It’s rare that I’d ever partake in a meal this extensive or expensive on my own, so having the planning aspects taken care of really felt like a treat – it wasn’t all that dissimilar from sitting down to a chef’s prix fixe menu at any upscale dining establishment, except that between each course, you took a flight of stairs, monorail ride, or both.

Parting Thoughts

A few things to keep in mind: you do not get to pick any of the food or drinks you sample (except water/sodas available at every stop). As stated earlier, I imagine as the seasons change and as feedback begins to roll in regarding the current menu offerings, food and beverages offered in later events may change slightly (just as menus do at all of these restaurants regularly). Additionally, many portions of the event take place outdoors and standing up. These factors could impact your enjoyment of the experience – I was lucky enough to attend on a beautifully cool evening, and had no issues with the stairs/standing (to me, no more taxing than a regular day at the park).

Overall, the Highway in the Sky progressive dinner made for a fun night – I’d recommend it if you are celebrating a special occasion and have an entire evening to spend doing so. If you’ve never dined at some of these establishments, this dinner is a great introduction to some of their signature offerings. If you’re well-versed in the dining venues on the Magic Kingdom monorail loop, this dinner still has a place for you; Disney takes care of all of the logistics, offering a unique and dynamic change of pace to a standard static meal, a new way to try all of your favorites in one whirlwind evening.