Hi, Wayne! I've had the
Highway in the Sky Dine Around progressive dinner on my Disney bucket list since it premiered in 2016. The event is held most Monday- Thursday nights, and is capped at a total of 25 Guests. Five courses are served at three stops along the monorail-
Disney's Contemporary Resort, Disney's Polynesian Village Resort, and Disney's Grand Floridian Resort. Special dining experiences are often able to be booked 180 days in advance, but when I checked the website, I saw the same availability you did. I called and spoke with a Disney Dining Cast Member, and she said that Disney can be slow to commit to extensions, but she felt confident that the Highway in the Sky Dine Around would be continued, and perhaps you'd see some available dates around the 90-day mark. My advice would be to check the Walt Disney World website once a week- I did this for Early Morning Magic, and I was able to book it 90 days before my trip.
The dining event is hosted by three Cast Members who will whisk you away to each stop, and you'll get a seat in the first car of the monorail each time- it's like your own private chariot! At each resort, you'll be greeted by another Cast Member who will give you a history of the resort in addition to what the food offerings will be. At the end of the night, the monorail will make its last stop at the Contemporary Resort for a private viewing of
Happily Ever After from the Fourth Floor Observation Deck; it doesn't get more magical than that!
Wayne, I wish I could give you a more pixie dusted answer, but Mickey and I will be keeping our fingers crossed that you'll be able to make your reservations soon!
Eean