Pardon my novice, but does anyone know if it's possible to create guides like this in Maps, with a heading and descriptions and stuff?

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Thanks for bringing this up, the guides feature needs a serious overhaul, the fact that I can’t even add a simple note other than the title of the guide annoys me on a weekly basis. Having to resort to notes is clunky :(
- agreed!! i like that in google maps i can add little notes to places in my lists
  
  apple is so bare bones on that front, even just allowing a header and simple notes on each item would go a long way