The first day I would build
Give the city one clear route before adding extras.
- Start with Umayyad Mosque and Souq Al-Hamidiyah while energy is high.
- Use Old City as the natural reset instead of crossing town too early.
the easier plan is Souq Al-Hamidiyah and Umayyad Mosque area first, wider Old City only with current local advice. That keeps the day readable instead of turning every good name into a separate detour.
I would rather leave one place for tomorrow than drag a tired route through Straight Street just because it looked close on a map.