FYI - I'm working with a Disney Event Planner to do a private Highway in the Sky Dine Around on a Sunday in January (it's going to be a post-marathon celebration for my friends and I after we complete all the races that weekend) and my planner reported back today some info that I thought I might pass along!
1. Dining/Events is currently working to extend the calendar through January - it just takes quite a few departments to get approval for the event based on other events, staffing, busy times for bars and restaurants, etc. I was told that the schedule will likely change in the next booking group, with Sundays now becoming options for bookings.
2. The total capacity is 26 people.
3. You CAN book the entire event privately and make small tweaks to both the dining and drinks menu that will reduce the cost of the event per person (I'm below $150pp right now for my event) - for example, not having a "duet" main course ... I don't eat cooked fish EVER, so I certainly don't want that for an event I'm planning and paying for - so, because I know everybody attending, we're doing an either/or entree offering (short rib or scallops). If you book privately, portions of the event may be relocated to regularly-serviced areas - in my case, the Tea Room may not be available for champagne and accompanying course, so we might enjoy that portion of the trip in a reserved area of Mizner's. You can also order a cake instead of a dessert tray for the private event.
4. If you're traveling in a large group from another resort, see if they will exchange your free valet parking per person for a comp'd van ride or Suburban. This was an option for me, and frankly? It should be open to everybody because the Contemporary has a fleet of Suburbans that can make quick stops and pick up the on-site people paying for this experience.
Anyway - if you'd like more in-depth details about planning a private event, I'd be happy to share! I don't know if I'm the VERY first person to request this, but I'm one of the first to follow through and place a deposit. I've been trying to plan it to be flexible in hopes that it might be something people can also book going forward in larger groups.