We have 2 different nights of activities planned at 2 different venues planned for our reunion.
Is it possible to post maps for both venues?

Our system has 1 map area by default as you've noticed, but all that map is really doing is plugging the zip code/street address into Google Maps and then showing the live map. Because you want to put in two interactive maps I actually recommend you turn our default mappting feature off. Then:

1) Go to maps.google.com
2) Generate a map for your first location
3) Click the "Link" link at the far right
4) Copy the code under "Paste HTML to embed in website"
5) Go back to your reunion planner, click the Source button, and paste in your source code for your first map
6) Repeat steps 1 through 5 for your second map

This way you'll have both interactive maps on your reunion page.