How it worked...
We met at a designated location and then moved through St. Louis to our parents houses, siblings houses, family Christmas parties, where ever the group wanted to go - all planned in advance. Our families looked forward to it and it was such a fun and unique way to celebrate the holidays.
We also did it for charity and collected money for the St Louis Christmas Carols Association.
About a month out I sent an evite to see who all was interested or available that year. Everyone was welcome - we were not all the best singers (I can say that because I'm one that's not). Then I would find a limo - we used Party Time Limo year one and JED Transportation year two.
After we knew who was going I would find out if they had a place they wanted us to carol at - then I took all the addresses and made a logical Google Map for the bus driver with a time schedule so we were sure to get to our final destination on time - we ended at a bar or house party where other friends would meet up with us following caroling.
I made the song books by looking up the most common carols from Google. This is a great site for finding the lyrics to common Christmas Carols. Keep in mind you can only sing about 3 sometimes 4 (ending with "We Wish You a Merry Christmas"). As the group progressed through the night we had our favorites - that we were "good" at and then we were mostly singing the same tunes. We always chose our songs before we left the bus so we ready to sing when we are all on the porch. Make sure to choose familiar songs.