Highway in the Sky Dine Around Review: Is Disney’s Progressive Dinner Worth It?

Have you ever heard of the Disney World Highway in the Sky Progressive Dinner? I’ll have to admit, I had never heard of it until I was researching Disney World adults-only activities for a recent AAA Traveler article that I wrote.

When I saw a few mentions of the Disney World Highway in the Sky Dine Around, I was DEFINITELY intrigued! I feel like I’ve done almost everything at Walt Disney World, having previously worked for the company for so long (even onboard the Disney Cruise Line) and living here for over a decade.

And yet, I had NEVER heard of the Disney progressive dinner.

Why?

Probably because it’s so hard to get a reservation. And because it’s so expensive. And no one seems to be talking about it.

A reservation for 2 people opened up on the exact date that I was looking for, by the Grace of God, so we decided to splurge and see what the Disney World Highway in the Sky Progressive Dinner was all about.

This is our honest Highway in the Sky Dine Around review. We paid for both tickets, it was not a complimentary press event.

What is Highway In the Sky Dine Around?

Disney’s Highway in the Sky Dine Around Progressive Dinner is an upscale evening of tasting food at the three Disney resorts on the monorail loop:

• Contemporary Resort
• Polynesian Resort
• Grand Floridian Resort

Sure, you can do the same thing on your own. But it will take more time and you won’t get some of the perks.

*If you do want to make your own monorail crawl, I LOVE this Monorail Crawl Ticket Book which is SO CUTE!!! Or get a monorail crawl lanyard to check off ideas on your bar crawl. (P.S. Wear this brilliant shirt while doing it and you’ll get so much attention!)

You see, by reserving one of the coveted spots on the Disney World Highway in the Sky Dine Around, you’ll be guaranteed a private monorail car for your entire group during the progressive dinner. There is no waiting in line to wait for a monorail like you would be doing it on your own.

Is that perk alone worth it? Well, it’s pretty sweet to walk off a monorail and your car is the only one with the doors open (see our video later on below).

When all of the other Disney guests are still in the monorail waiting to disembark, and your group is the only one being left off to walk into each resort, you do feel like a celebrity.

You will also be given a private fireworks viewing point and dessert party at the end of the night. Seeing the Magic Kingdom fireworks with no crowds is pretty awesome, too.

If you’re looking for one of the Disney for adults experiences, the Highway in the Sky Dine Around is for you. It’s an especially great way to celebrate a birthday at Disney World.

There won’t be a lot of strollers or screaming children in your party. Disney suggests children only 12 or older attend the event. In some instances, younger children have been on the progressive dinner, but it’s definitely not a child-friendly event. (It’s a LOT to pay for a child, since the price is not pro-rated if you don’t consume the alcohol options during the dinner.)

The menu is a prix fixe menu, so if you want more flexibility in what you order, this event is not for you.

Note, this is NOT the unofficial Monorail Bar Crawl. That is a popular, self-guided way of visiting bars along the monorail loop. Disney does not have an official event for this (at least not yet).

How Does the Monorail Dine Around Work?

You’ll be checking in at The Wave restaurant in Disney’s Contemporary Resort. Everyone will check in at a designated lounge area to the right when you walk in. You will get a lanyard and name tag button to wear during the evening.

Then, you’ll start chatting (or maybe not) with the people around you until the first course is served.

A representative from The Wave will come and discuss The Wave and their dining options, while serving a cocktail and an appetizer.

At a designated time (no exceptions), you’ll be escorted upstairs to the monorail. The front car of the monorail will be held for your group. On our monorail dine around, three Disney cast members were the leaders, making sure everyone was together and leading the way.

There was a brief introduction before dining at both the Polynesian Resort and Citricos at the Grand Floridian. I felt that these introductions were kind of silly, especially since so many of us were Disney fans and knew the information already. Plus, it really ate up the time that we could instead be eating.

After each course of the progressive dinner, you will have a specific time that you need to leave. You will be given a 5 minute warning, but do not delay. The timing coincides with when the monorail is arriving. The monorail will be held for your group.

The great thing is that you don’t have to go through security every time you get on the monorail. There will be a Disney transportation cast member that also works with your group. He or she will bring you through the lines of guests and arrange for the monorail to be available for you.

How Many People Will I Be Eating With?

The progressive dinner guest list is kept small.

Expect around 25 people (or less) to be traveling with you.

After all, the capacity is only as much as a monorail car will allow.

For the first two courses, you’ll likely be in communal settings and might be dining with others at a table, or find a small table of your own.

For the Citricos course, you will be assigned a place at a large round table with other guests.

The fourth course of cheese and sparkling wine will have you at your own table.

The fifth course is a buffet with high top tables and open seating.

When is Disney’s Highway in the Sky Dine Around held?

This progressive dinner is not held every night. Which makes trying to find a reservation more difficult.

Currently, it is available Monday – Thursday nights.

How Can I Book Disney’s Progressive Dinner?

Reservations can be made online with Disney Dining (be sure to search under the Contemporary Resort as the location), just as with all other Disney Dining reservations.

How Much is the Highway in the Sky Dine Around?

The Disney Highway in the Sky price can leave most Walt Disney World guests in sticker shock. It’s a hefty $170 per person (includes food and alcoholic drinks). Gratuity IS included. However, tax will be added onto the $170.

Is it cheaper if you don’t drink alcohol? Nope.

Is there a child’s price? No.

If you cancel within 24 hours, you’ll forfeit the deposit you have put down.

Valet parking is included in the price of Disney’s Highway in the Sky Progressive Dinner. Tip is not included. And you don’t have to valet park if you choose not to.

There are no discounts or promotions. You cannot use Disney Dining credits or meal plans to pay for the progressive dinner.

What is the Menu for the Highway in the Sky Dine Around Progressive Dinner?

This progressive dinner is a seasonal, prix fixe menu. Which means there are no variations and no substitutions unless you have contacted Disney beforehand (at least 24 hours in advance).

The menu for Highway in the Sky seems to vary with each review, yet somehow stay very much the same. Confusing, I know.

The places where you dine will be the same. And you’ll generally get the same type of food. For instance, you’ll likely get a soup and a cocktail at The Wave at Disney’s Contemporary Resort. And three different tastes of entrees at the Polynesian Resort.

But the type of soup and the type of cocktail will change depending on when you go.

Here is our dinner menu when we enjoyed the Disney World Highway in the Sky Dine Around in March 2019 (see all of the foods detailed in our video):

The Wave at Disney’s Contemporary Resort

• Pea Soup
• Discovery Island Fizz with Strawberry cocktail

Disney’s Polynesian Resort

• Roasted Potatoes and Filet of Beef
• Tune Poke with Shrimp Chip
• Hawaiian Fish with Ginger Cream Soy Sauce
• Mai Tai cocktail

Citricos at Disney’s Grand Floridian Resort

• Beef Short Ribs
• Red Snapper
• Red or White Wine

Garden View Lounge at Disney’s Grand Floridian Resort

• Cheese
• Charcuterie Board
• Sparkling Wine

Dessert Reception at Disney’s Contemporary Resort

• Organic Chocolate Flourless Cake
• Key Lime Cheesecake Bar
• Florida Strawberry Shortcake
• Liquers and Coffee Bar

Parting Gift of Truffles at the End

Birthday Dessert

This is the dessert that my husband received at the Dessert Party for his birthday.

What About Food Allergies? Can I Still Enjoy the Highway in the Sky Dine Around?

This was one of my biggest fears when booking Disney’s Highway in the Sky progressive dinner for my husband’s birthday.

While we avoid many food items, I am definitely allergic to a variety of things. But not just ONE thing. 

If I could have seen the menu beforehand, it would have been a lot easier to say “Yes, this is fine” or “No, I need a substitution.” But that information is not available beforehand.

Alerting Food Allergies – And Needing to Double Check

I did note my allergies when I booked the progressive dinner. However, I don’t think my allergy notification was seen.

When I received a confirmation call a day or two before our Highway in the Sky Dine Around, I asked if my allergies had been noted. The Disney cast member (whom I found out would be one of our “leaders” on the dinner tour) said there was no allergies noted.

YIKES!

She asked me what my allergies were, and I asked if she had a pen and paper ready because it would be long.

In all honesty, she was a bit overwhelmed with everything I told her. But I needed to make sure every single fruit that might show up in a dish, from blackberries to guava to passion fruit, was noted so that I could eat all of the very expensive food.

I did tell them that I couldn’t eat seafood. Thank God that I did. Because at least 50% of all the foods served were seafood based, it felt like.

After much discussion, I finally asked if she knew what the menu was. She did. While the cast member didn’t tell me exactly what was on the menu, she did give me an idea that there was seafood dishes at most stops.

I’m assuming that maybe with extensive questioning 24 hours beforehand, you could probably find out what the menu is for allergy safety. What some guests will not feel comfortable with, though, is that you can’t talk directly to a chef about your concerns before the food is prepared.

I was given a card to hand to the waiter at Citricos. Other than that, there was no obvious way that my dinner stood out when being given the food. The servers were very aware of who had the allergies. Probably because it was such a small group and they could be told easily by our Disney cast member leaders.

What Should I Wear? Is There a Dress Code?

There is no mandatory dress code to wear formal clothes for Disney’s Highway in the Sky Dine Around. They simply ask that you adhere to minimum dress code requirements. 

Minimum dress code requirements are (according to Walt Disney World):

Men must wear khakis, slacks or dress shorts and collared shirts. Jeans may be worn if in good condition. Sport coats are optional.

Women must wear Capri pants, skirts, dresses or dress shorts. Jeans may be worn if in good condition.

Not permitted are tank tops, flip-flops, swimsuits, swimsuit cover-ups, hats for gentlemen, cut-offs, torn clothing and t-shirts with offensive language and/or graphics.

As you can see, the minimum dress code requirements are pretty common sense for a $170 dinner experience.

On our Highway in the Sky Progressive Dinner, there were a variety of clothes worn. Overall, most people chose to dress up, as if they were going to a nice dinner. A few wore more casual resort wear, such as a Hawaiian shirt and khakis. 

If you dress up, you won’t feel out of place. If you don’t have formal clothes with you on vacation, you won’t feel out of place, either.

Walt Disney World Highway in the Sky Dine Around Review: Is the Progressive Dinner Worth It?

So, is this monorail progressive dinner worth it?

That depends.

There’s a lot of factors to take into consideration. 

Highway in the Sky Dine Around tends to be a dining experience for couples, especially those celebrating anniversaries and birthdays. That’s not to say there wasn’t groups of friends or singles in the group. It just skews towards couples.

The cost is a huge factor. Especially if you don’t like to drink or plan on drinking.

The Disney progressive dinner isn’t a great choice for guests that are new to Disney World. While you can certainly get a small sampling of the different resorts and menus, you’d be better off doing it on your own. Make a dining reservation at one of the resorts (keep in mind these Disney restaurant secrets), and then take the monorail to visit the others on your own time.

A lot of the guests on our Dine Around were Disney fans or frequent Disney visitors. Most people seemed to come to the Walt Disney World Resort a few times a year, or were DVC members. A few local residents were on the progressive dinner, too.

Here the pros and cons for the Disney World Highway in the Sky Dine Around Progressive Dinner:

Pros

• Exclusive Experience
• Limited capacity
• Adults oriented dining 
• Talk with other Disney fans
• No worries about catching transportation
• Once-in-a-lifetime opportunity to board a private monorail car and feel like a celebrity with special access
• Guaranteed fireworks viewing site
• Plenty of alcohol served if you drink

Cons

• Very strict time line
• No chance to explore the resorts
• Prix fixe menu which you might not like and don’t know in advance what it will be
• No refills on alcoholic drinks – only one glass
• No price discount for those who don’t drink or for those under the drinking age
• Price

Am I glad we indulged in the Disney World Highway in the Sky Dine Around? Yes!

Would I pay for it again? No. 

While I loved the unique experience of riding the monorail in an exclusive group, the overall value for the food and drink included was just a huge price tag. I would prefer to be able to get large portions of my own choosing.

I would also like to have the time to sit and enjoy my meal or drink, rather than rushing through every experience.

And if I’m at a resort, I prefer the opportunity to enjoy the location, such as walking by Bay Lake at the Polynesian Resort. You don’t have time to do those things on the monorail progressive dinner.

More Exclusive Disney Experiences

Like fewer crowds and special experiences? Then you’ll love Disney’s Early Morning Magic at Toy Story Land. 

Also, check out Disney After Hours, which is a chance to enjoy Disney’s theme parks with fewer crowds.