Disney World has a progressive dinner around the monorail resorts called the Highway in the Sky Dine Around. I booked this dinner experience for my birthday in March and it formed the crux of my birthday week in Florida. Now I’m here to tell you what an amazing experience it is and everything to expect if you go.
Highway in the Sky
First, the basics–what’s this “Highway in the Sky” business? I don’t feel like I hear it referred to much this way anymore, but the Disney Monorail–those trains on concrete beams that circle Seven Seas Lagoon in front of the Magic Kingdom–was pitched as the “Highway in the Sky” in the ’70s when Walt Disney World opened in Florida. It feels like a very ’60s progressive term when highways were a new and exciting thing. And here we have one in the sky! It’s Disney magic.
When I hear the term now, it makes me think of the original Jack Wagner voiceover that used to play in the monorails back then. I’m not even sure if I heard that version as a kid, but it sure makes me feel nostalgic now!
The monorail connects the Magic Kingdom to the three Magic Kingdom resort hotels and the Transportation and Ticket Center. An express monorail travels in the opposite direction stopping at just the Magic Kingdom and the TTC. Pro tip: at the end of the night in the Magic Kingdom when everyone is getting on the express monorail, the resort monorail may actually be quicker, even though it makes more stops.
Dine Around
Are we all familiar with the idea of a progressive dinner? It’s where you break down a meal into separate courses (appetizer, main, and dessert, at least) and have each course in a different location. I tend to associate progressive dinners with the Christmas holidays when different families would host one course at their home and a crowd of folks would travel from house to house. It’s also a fun way to explore several restaurants in your own home town, with three or more different stops in a night. I did this once with a group of friends and it was super fun! We still talk about it, years later.
In England, I’ve heard they call it “safari suppers” which I absolutely LOVE.
Highway in the Sky Dine Around
Therefore, the Highway in the Sky Dine Around is a progressive meal around the monorail resorts, using the monorail to travel between each stop. At the start of our evening, we were given lanyards indicating we were with the group and a name tag. Between stops, we always had one entire monorail rail car reserved just for our group.
General Atmosphere
I travel solo all the time, and I didn’t think a thing about booking this dinner as a party of one. It wasn’t until I was driving to the Contemporary that it even occurred to me that it might be awkward, that I might be the only solo person there. After I checked in, one of the Disney ladies assured me that this is a GREAT event for a solo person, that by the end of the night we would all be friends and I found that to be absolutely true!
I never was at a loss for someone to talk to or sit with, and they kind of notice who you gravitate towards and arrange things accordingly along the way. I didn’t meet everyone in the group, but I had a really fantastic time with the 4-6 folks that I tended to hang around. Plus, everyone is drinking alcohol at each stop, so that really ups the friendliness factor.
First Stop–Contemporary Resort
If you are driving yourself to the Highway in the Sky Dine Around, you get complimentary valet parking at the Contemporary Resort. This was kinda fun for me since I would never spring for anything so expensive myself. It’s a little funny too, to get valet service on my 13-year old car on which the bumpers sometimes fall off.
You check into The Wave on the ground floor of the resort, not up in the Grand Canyon Concourse. It’s straight ahead from valet parking past the check-in desk. Inside The Wave, they seat all attendees in a very blue lounge near the bar.
You wait here until everyone arrives and they hand out the lanyards and name tags. The general manager of The Wave gave a little speech about the restaurant (almost a pitch to come back) and about the food they were going to serve. This turned out be a pattern–at every stop, we’d get a little informative speech about the restaurant or hotel and what we’d be eating before we were seated and served.
The Food
At The Wave, we received one full-sized drink and one tiny appetizer/amuse-bouche. The drink was a gin cocktail with elderflower liquor garnished with cucumbers and strawberries. (Sadly, I ate the garnish out before I took a pic, my apologies.)
The amuse-bouche was a small espresso-sized mug of pea soup topped with mushrooms and truffle oil. Both of these items were my least favorite of the night and I didn’t finish either one. In fact, the general consensus of the group was that pea soup was a bad move–no one seemed to like it.
Stop Two–Polynesian Village Resort
From The Wave, we were led together through bag check and up the escalators to the monorail. The monorail runs right through the middle of the Contemporary Resort, so you board it upstairs in the open Grand Canyon Concourse (which never stops being cool.)
The next stop on the monorail is the Polynesian Village Resort, where we were led to a spot just to the right of the doors. Two long tables were set up for us and we were greeted with plastic leis and a ukulele player!
The Food
A fruity Mai Tai was our drink for this tropical location and I liked it much better than our gin cocktail.
Our food at this stop was supposed to be “appetizers” but it could serve as a meal in any normal situation. We were served three items–filet over purple potatoes, tuna poke, and fish over bok choy.
The filet and potatoes were good, and the tuna poke had mango bits in it, which I liked very much. The tuna was topped with what I thought they said was a “shrimp crisp” but it didn’t taste like much so maybe I was wrong about the shrimp part. I think the white fish over bok choy may have been my favorite. It was in an Asian sauce that was quite good and provided some of the precious few vegetables of the night.
Stop Three–Grand Floridian, part 1
Back on the monorail again and on to what was considered our “main” meal at the Grand Floridian Resort. For it, we were led downstairs to Citrico’s, an American-Mediterranean restaurant near the back of the lobby.
You are assigned seats at this location, and this is where your chaperones will prove how well they’ve been spying on you. I sat with the couple I had sat twice with so far plus a new (to me) young couple. The spies’ judgment was excellent–we all ended up hanging out together for the rest of the night.
You get a little bit longer at this location too. Not that any of it is rushed, but you don’t linger too terribly long at any one place.
The Food
The food here was two small servings, one of short rib and one of red snapper. The snapper was very good and served over a pittance of greens. The short ribs, however, were out-of-this-world! The beef simply fell apart when touched and absolutely melted in your mouth. This excellent beef was served over a mashed potato puree. The course is served with your choice of either red or white wine.
Stop Four–Grand Floridian, part 2
After dinner in Citricos, they led us down the hall to the Garden View Tea Room for a cheese plate and champagne. This was the only point in which my single status ever-so-slightly reared its head, for they sat each party at its own intimate little table. This left me at a table by myself. But I had been put between two other couples, one pair I had already met and one I hadn’t. There ended up being an ongoing conversation between all three tables, so I didn’t feel lonely at all. Remember, by this point, we were all three drinks deep and full of excellent food and pretty pleased with everything and everyone!
The Food
We were all getting pretty full by now, so most of us picked at our cheese plates, and I only drank half of my champagne. The plate consisted of two cheeses, a brie and a blue, and three meats served with sweet pickles, honeycomb, whole-grain mustard, and some crusty bread.
Stop Five–Contemporary
Back on the monorail to the Contemporary Resort, we headed to the Magic Kingdom side of the Grand Canyon Concourse where a spot on an outside terrace had been reserved for us.
Inside, there was a small dessert buffet set up on one side and hot coffee and liqueurs on the other. Once you got your food, you can head outside to eat and then view the evening fireworks from the Magic Kingdom. It was a great ending to the night, even though it rained on us a bit there at the end. I hadn’t seen the Happily Ever After fireworks show yet, so I was excited to see it from such a unique spot!
The Food
The grand finale to our evening of eating were three dessert options–a flourless chocolate cake, a key lime cheesecake bar, and strawberry shortcake in a shot glass. Of the three, the chocolate cake was my favorite, then the strawberry shortcake, which had a great crust on the bottom. The key lime bar was good, but I wished it had been a true tart key lime pie instead of the muted flavor of cheesecake.
The pour of Bailey’s in my decaf coffee was extremely generous, almost half and half. That last one did me in a little and I ended up riding the monorail around before driving home for the night.
Fireworks
The view from this terrace is pretty cool–you get the monorail right over your head and some fun picture opportunities of it approaching the resort. Then the fireworks appear mostly over Space Mountain. There are even a few rows of seats in this corner if you ever find yourself here and it’s not blocked off.
Event Details
If you want to book the Highway in the Sky Dine Around, the cost is $175 per person and it’s a good idea to book pretty far in advance, particularly if you want a specific date. The Dine Around occurs most Monday-Thursdays, so no weekend dates are an option.
I was originally looking at a date closer to my actual birthday, but that evening became fully booked 2-3 months ahead of time. On the other hand, one couple I hung out with most booked just a couple of days in advance, most likely due to a cancellation. So you never know!
Finally, while the food is amazing, the concept really cool and done with Disney excellence, my favorite part about the evening was the people that I met and how much fun we had together. I would highly recommend it to anyone who can reasonably afford it for a special occasion. It’s not a must-do or integral to your enjoyment of Disney World. Just a fun extra if you can swing it.
The only way I could afford it is because my sister had given me $100 in Disney rewards, so I used that toward my birthday meal. That still left me with $80 to cover, and that’s still pretty high for me, but it was certainly worth it!
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