Childrens Film released between 2000-2007

Question

I have a strong memory of a dvd I used to watch as a child where a group of children (real life) go to different places with the narrator/presenter (I remember him being black) and it’s a musical/sing along film where they sing songs. I definitely remember “how much is that doggie in the window”’and a pirate song included and i remember at the end they are all sat around and Rupert the bear (a man in a Rupert costume) comes and greets them all

I CANT REMEMBER WHAT THIS WAS

Answer 1

If it was American, my suspicion is that the DVD was a collection of segments from one of the PBS Kids shows from the 90s. It could have been KidSongs or Zoom. Neither of those shows had a host to my knowledge or my research, but the DVD could have had one. It's also possible that it could have been a Reading Rainbow special. Alternatively, it could have also been a DVD that had a collection of episodes from multiple shows all put in one. Follow that route if you think I'm right. The 90s saw loads of DVD children's content that was just repackaged TV episodes.