WL and VWL guest both can be Flag Family.
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Wilderness Lodge Flag Family,
from someone who has guided many Flag Families and done the "ceremony" many times:
1) You request at-or-after check-in.
2) You cannot request prior to arrival date or check-in (WL guests only).
3) If you are staying a full week or more, you have a good chance.
. . . most people stay less than 1-week
. . . thus, the 6th day, 7th day, or later, may still be open
4) The other good chance is to check-in VERY early in the day.
5) First-come-first-served, but there is a wait-list.
6) Rules
. . . no more than 5-guests, since with guide, that is six people
. . . must respect the flag
. . . not handicap accessible
. . . climb stairs - one long steep inside stairway and one outside steep flight
. . . not afraid of heights, as you are about 90-feet in the open air
. . . fog, rain, mist can cause cancellation, with no rescheduling
. . . children must behave, because roof can be a dangerous place
. . . cameras and video recorders are allowed, as all four parks are visible
7) The Flag Family
. . . gets an escort to the top of Wilderness Lodge to raise all the flags
. . . gets a story on the flags and some WDW history
. . . can pose on top of the rooftop for photos
. . . can see every part of WDW, including all four parks
. . . gets a souvenir certificate with their name and date noting the occassion
. . . there is one Flag Family per day
NOTE: Requesting to be a Flag family ahead of time is not fair to others.
Also, there is no way to make certain you will keep your hotel ressies and
be there for your Flag Day. Should you not cancel, then there is a day that
someone else could have taken. It is just better to have people wait until
they arrive to request a day.