(The Tim Gunn itinerary is further down the thread here, Tiger Woods is here, Paula Deen part 1 is here and then there's part 2)
The scenario is hypothetical, the itinerary is realistic. I'll be ready the next time a family of 20+ asks me for advice!
Let's assume:
The Duggar family and their WHOLE family want to visit Disney World for 5 days sometime in early December. They'll drive to get there (2 dozen plane tickets would kill anybody's budget and they have an RV!) but everything else is TBD.
My plan:
First of all, congratufreakinglations for taking that whole brood out. I only have 2 and it sometimes feels like a big giant deal to get us going. Not to mention something like 20ish people (I've stopped counting Duggar family members. I'm pretty sure Jim Bob has as well.).
Ok, where to stay? Not even the huge rooms at the Poly or the nicely sized cabins at Ft. Wilderness will work for this many people. I would go for booking 4 rooms at a value resort and make sure they are connecting (not just adjoining but connecting! That means the doors will open between them.) which gives 8 beds and 4 bathrooms. Extra cribs and rollaways could also fit in the rooms which would provide enough space for everybody. May I suggest Pop Century as your value resort? They have their own buses to the parks which is AWESOME. Especially when you're at a bus stop with a whole bunch of tired kids.
As for the exact dates, I say it doesn't really matter tooooo much as long as it's in the first 2 weeks or so of December. It's often considered the best time ever to visit because of the mild temps, low crowds and beautifully amazing Christmas decorations. Weekend rates are a little higher so if you're choosing any 5 days, pick the weekdays.
Now! What to do when you get there? It's hard to start any Disney trip with kids off with anything OTHER than Magic Kingdom. It's what they picture when they think Disney World and taking them to Animal Kingdom might very well be a huuuge let down to kick off a trip.
After checking in on Monday, head out to the bus stop and catch the bus to the Magic Kingdom. Ride the train around the whole park to get a feel for it, maybe catch an afternoon parade and keep it easy and laid back. Leave Magic Kingdom and take the monorail to the Contemporary resort for an early dinner at Chef Mickey's. It's super fun for everybody and there's characters and a buffet so everybody gets to eat right away. And taking the monorail is just plain fun! If there are fireworks scheduled at Magic Kingdom that night, head to the deck to view them right from the Contemporary.
After dinner, take the monorail back to the Magic Kingdom (or walk, if you'd like) and catch the bus back to Pop Century. Call it a day since you're likely exhausted from all of the traveling and need to rest up for 4 full days ahead!
The next day is Tuesday and while it would be super quick to have a Pop Tart in the room, you should really head back to the Magic Kingdom by 9:30 because you're going to have a super special breakfast called the "Good Morning Gathering" which allows you to eat in Tony's Town Square Restaurant and then have some one-on-one time with Mickey himself! This isn't a normal event. Having all of those kids is finally going to come in handy because this is a special event only available to groups. Minimum for this is 8 people and you have, ummm, more than twice that much. PLENTY. After this special event, spend the rest of your day riding rides and make sure to use FastPasses if lines get long. If some of the Baby Duggars don't want to ride, the Parent Swap thing is awesome. Try it.
After you've worn yourself out on Magic Kingdom, take the monorail over to the Grand Floridian. This is Christmastime and you need to see this hotel and the gingerbread houses. Take some time to tour, maybe buy a mini-gingerbread house (or 18) for yourselves and head back to the Pop Century to eat some food court dinner.
It's Wednesday! It's also EPCOT Day! Take the buses to the front gate of EPCOT (be there when it opens!) and explore the front section of the park called Future World. Soarin' is the most popular ride so either head there first or go snag some FastPasses there first so you don't have to deal with fussy kids waiting in huge lines later. Be sure to catch Turtle Talk with Crush, the aquarium, Test Track and Mission: Space for those who are brave enough (little ones can play in a very nice exit area on this ride if they can't ride themselves).
After touring the Future World section, head to the back section called the World Showcase. Take your time walking through the different countries and enjoy the Christmas decorations. Be sure to go to the amazing Candlelight Processional at 5:00 pm, 6:45 pm or 8:15 pm but this has to be booked beforehand.
Over in the U.K. and Canada sections of the World Showcase, there's a bridge that lets you exit the parks and head to the Boardwalk area where the Beach Club/Yacht Club and Boardwalk hotels are. Stop by the Beach Club for an ice cream, check out the hotels and their Christmas decorations, play some games on the Boardwalk and maybe grab some pizza at the pizza window. I'm positive the whole gang is exhausted by now (except for the teen girls in the group who are probably ecstatic they are off cooking duty for 5 days) so head back by taking the boat from the Boardwalk to The Studios and catch a bus to Pop Century from there. You could walk/boat back to EPCOT but it's a long walk back to the front of the park that way.
It is Thursday and I. am. exhausted. The whole fam could probably use a little time to sleep in so let them do that and then head to Animal Kingdom. Start off with getting some FastPasses on Expedition Everest if lines are too long. The busiest rides are that coaster and the safari but no need to do the safari just yet! After that, you should have a pretty easy time doing everything else. At park closing time, you're going to take part in a special Safari Celebration Dinner (another Magical Gatherings event) which gives you a private guide on a safari and then dinner at Tusker House where you'll also get to see some real live animals from the park along with some characters. Head back to the hotel after that. One day left!
Friday, the last day at Disney World. If you hadn't guessed yet, today is the day to do the last park in the Disney World area: The Studios. Head over there on the bus and try to catch as many shows and ride as many rides as possible. I believe in ending trips with a bang and seeing Fantasmic is a great way to do that. It's a little dark for little ones but a really great show. The times schedule can vary and there may NOT be one scheduled for this night so check before you go.
We managed to work in all of the highlights for this 5 day trip for 83 20+ people including viewing lots of Christmas decorations which is a huge perk this time of year. If you come back again, maybe make it in the summer where you can break out the WholesomeWear, mmkay?
Update/Correction: I mentioned watching fireworks at the Contemporary from the deck. The 15th floor deck is for California Grill diners only. The 4th floor deck is open to everyone so that's where our favorite family of 20/22/89/whatever would need to go.

The scenario is hypothetical, the itinerary is realistic. I'll be ready the next time a family of 20+ asks me for advice!
Let's assume:
The Duggar family and their WHOLE family want to visit Disney World for 5 days sometime in early December. They'll drive to get there (2 dozen plane tickets would kill anybody's budget and they have an RV!) but everything else is TBD.
My plan:
First of all, congratufreakinglations for taking that whole brood out. I only have 2 and it sometimes feels like a big giant deal to get us going. Not to mention something like 20ish people (I've stopped counting Duggar family members. I'm pretty sure Jim Bob has as well.).
Ok, where to stay? Not even the huge rooms at the Poly or the nicely sized cabins at Ft. Wilderness will work for this many people. I would go for booking 4 rooms at a value resort and make sure they are connecting (not just adjoining but connecting! That means the doors will open between them.) which gives 8 beds and 4 bathrooms. Extra cribs and rollaways could also fit in the rooms which would provide enough space for everybody. May I suggest Pop Century as your value resort? They have their own buses to the parks which is AWESOME. Especially when you're at a bus stop with a whole bunch of tired kids.
As for the exact dates, I say it doesn't really matter tooooo much as long as it's in the first 2 weeks or so of December. It's often considered the best time ever to visit because of the mild temps, low crowds and beautifully amazing Christmas decorations. Weekend rates are a little higher so if you're choosing any 5 days, pick the weekdays.
Now! What to do when you get there? It's hard to start any Disney trip with kids off with anything OTHER than Magic Kingdom. It's what they picture when they think Disney World and taking them to Animal Kingdom might very well be a huuuge let down to kick off a trip.
After checking in on Monday, head out to the bus stop and catch the bus to the Magic Kingdom. Ride the train around the whole park to get a feel for it, maybe catch an afternoon parade and keep it easy and laid back. Leave Magic Kingdom and take the monorail to the Contemporary resort for an early dinner at Chef Mickey's. It's super fun for everybody and there's characters and a buffet so everybody gets to eat right away. And taking the monorail is just plain fun! If there are fireworks scheduled at Magic Kingdom that night, head to the deck to view them right from the Contemporary.
After dinner, take the monorail back to the Magic Kingdom (or walk, if you'd like) and catch the bus back to Pop Century. Call it a day since you're likely exhausted from all of the traveling and need to rest up for 4 full days ahead!
The next day is Tuesday and while it would be super quick to have a Pop Tart in the room, you should really head back to the Magic Kingdom by 9:30 because you're going to have a super special breakfast called the "Good Morning Gathering" which allows you to eat in Tony's Town Square Restaurant and then have some one-on-one time with Mickey himself! This isn't a normal event. Having all of those kids is finally going to come in handy because this is a special event only available to groups. Minimum for this is 8 people and you have, ummm, more than twice that much. PLENTY. After this special event, spend the rest of your day riding rides and make sure to use FastPasses if lines get long. If some of the Baby Duggars don't want to ride, the Parent Swap thing is awesome. Try it.
After you've worn yourself out on Magic Kingdom, take the monorail over to the Grand Floridian. This is Christmastime and you need to see this hotel and the gingerbread houses. Take some time to tour, maybe buy a mini-gingerbread house (or 18) for yourselves and head back to the Pop Century to eat some food court dinner.
It's Wednesday! It's also EPCOT Day! Take the buses to the front gate of EPCOT (be there when it opens!) and explore the front section of the park called Future World. Soarin' is the most popular ride so either head there first or go snag some FastPasses there first so you don't have to deal with fussy kids waiting in huge lines later. Be sure to catch Turtle Talk with Crush, the aquarium, Test Track and Mission: Space for those who are brave enough (little ones can play in a very nice exit area on this ride if they can't ride themselves).
After touring the Future World section, head to the back section called the World Showcase. Take your time walking through the different countries and enjoy the Christmas decorations. Be sure to go to the amazing Candlelight Processional at 5:00 pm, 6:45 pm or 8:15 pm but this has to be booked beforehand.
Over in the U.K. and Canada sections of the World Showcase, there's a bridge that lets you exit the parks and head to the Boardwalk area where the Beach Club/Yacht Club and Boardwalk hotels are. Stop by the Beach Club for an ice cream, check out the hotels and their Christmas decorations, play some games on the Boardwalk and maybe grab some pizza at the pizza window. I'm positive the whole gang is exhausted by now (except for the teen girls in the group who are probably ecstatic they are off cooking duty for 5 days) so head back by taking the boat from the Boardwalk to The Studios and catch a bus to Pop Century from there. You could walk/boat back to EPCOT but it's a long walk back to the front of the park that way.
It is Thursday and I. am. exhausted. The whole fam could probably use a little time to sleep in so let them do that and then head to Animal Kingdom. Start off with getting some FastPasses on Expedition Everest if lines are too long. The busiest rides are that coaster and the safari but no need to do the safari just yet! After that, you should have a pretty easy time doing everything else. At park closing time, you're going to take part in a special Safari Celebration Dinner (another Magical Gatherings event) which gives you a private guide on a safari and then dinner at Tusker House where you'll also get to see some real live animals from the park along with some characters. Head back to the hotel after that. One day left!
Friday, the last day at Disney World. If you hadn't guessed yet, today is the day to do the last park in the Disney World area: The Studios. Head over there on the bus and try to catch as many shows and ride as many rides as possible. I believe in ending trips with a bang and seeing Fantasmic is a great way to do that. It's a little dark for little ones but a really great show. The times schedule can vary and there may NOT be one scheduled for this night so check before you go.
We managed to work in all of the highlights for this 5 day trip for 83 20+ people including viewing lots of Christmas decorations which is a huge perk this time of year. If you come back again, maybe make it in the summer where you can break out the WholesomeWear, mmkay?
Update/Correction: I mentioned watching fireworks at the Contemporary from the deck. The 15th floor deck is for California Grill diners only. The 4th floor deck is open to everyone so that's where our favorite family of 20/22/89/whatever would need to go.