Find someone to go with. Going alone isn't nearly as fun nor as musically interesting for the listeners as it is when you're with a bunch of other people. Make sure, that in total, you are at least three, five or more. If you don't know one another yet, that's fine also. You'll get to know each other well during rehearsals. And some people enjoy caroling as a family - there's a ready-made singing group for you provided everyone is willing! Find some Christmas songs everyone can sing. Choose the songs that everyone is comfortable with and that you believe will be the most enjoyed by the people in your neighborhood. Consider adding instruments if someone is good at playing a portable one, such as a guitar, tambourine, etc. Practice. It makes perfect as the old adage suggests and it's true. Rehearse together so that you not only know the tune and words but so that you are aware of each other's harmony and limitations. Yes, limitations! Don't have the person with the baritone trying the tenor and vice versa. It is also important that when you select the singers for your caroling group that you try to get a variety of voice capacities. Go door-to-door. Start with your own neighborhood.

Start off with the house next door. Ring the bell, and wait for it to open. Make sure you don't press the doorbell too much. Wait for a minute or two, and if it's not opened, then move onto the next. Sing. Once the door is opened, start singing. Gauge the reactions of the people at the door to see how long you should sing for.