As many have already said, Wonderdraft is great! I also recommend checking out its community subreddit, r/wonderdraft. And as u/BlindAngel said Watabou Fantasy City Generator is great for generating city layouts, which you can trace into wonderdraft and tweak to fit your tastes.
These tools really do make map making a joy.
Perhaps someone knows how to print with pins. But there's ways to print very large things across multiple pages. If you're interested, it's called tile printing, aka rasterbation. heh