The show is over. It was an incredibly long day (15 hour span: 2 techs & 2 performances & 3 hours of travel).
For this kind of event, it was great that the director was willing to be so flexible with the blocking. She was the only one who had been to the venues, and with no ground plan for either one (theater plot was not to scale and we were told we would "maybe have 5' of room downstage of the symphony" - and the google map of the winery had trees covering a lot of important items for us) it all went rather well.
The most difficult section was our fight in the Winery - as it was built to have 2 men with daggers up on a wall (away from patrons) while another set of actors did more "ham" fighting amongst the crowd - hitting each other with napkins, shoving appetizers in each others' faces, twisting nipples with wine glasses, etc. The two fights went on at the same time, but eventually a member of the hammy fight had to join the knife fight, so the two teams had to watch each other for timing - which was almost impossible given the volume of people in the space.
Our fight director had given the actors sections which could be cut or extended, depending on space, people in the way, etc. There were so many variables and none of us knew exactly what to expect prior to getting there. (We know there's a wine bar, we have no idea how far away it is from the scene action, how many people will block the actor's path to the bar, etc)
The rest of our scenes took place in a tent during dinner, and knowing that the platform were were on was 2' high and 12x12, that was easy to stage in advance. However, actors get used to the director and SM being on one side during rehearsals, and our 12x12 stage was in the round. During our rehearsal in the space, the director and I sat in various locations in the tent, so that the actors would pay attention to the fact that there was an audience on 4 sides.
I thankfully did have a PA (I would never have been able to do this without one - because the director really needed to schmooze with the Winery management and money people) and we timed our entrances (2 min 30 sec from the Winery House where we were changing/eating/relaxing to the stone patio waiting area, but 1 min 19 sec from the House to the staircase for scene 1, etc) and I worked with the event coordinator for the dinner to time out when we wanted the actors to arrive based on table bussing/wine refilling. I would station with the coordinator, and walkie to my PA an she'd send the actors.
I was kinda scared about the whole thing, but after seeing the venues and getting our 2 hours in each space (it helps to only have 26 minutes of acting with no real tech, so you can concentrate on spacing) I would do it again. And thankfully, the President of the Winery's wife went gaga for the show, so we will be doing this again.