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Italy for Beginners

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Sorry if I make any rookie mistakes- I'm new here. I appreciate any advice you all may have about travel (and forum etiquette!)

Here's the big picture:

Budget $5,000
Trip Date: Sometime in September
Trip Duration: ~2 Weeks
Travelers: Husband (seen Italy) & Wife (hasn't, but has always wanted to)
Tentative Locations List: Florence, Rome, Venice and Sienna(?)
Priorities:
Husband loves museums, ruins/historic sites, and architecture (Cathedrals, etc.)
Wife interested in Renaissance art ,Italian music, shopping, glass/ceramics workshops, and getting the "local" experience (likes Italian architecture and museums, too, just not as much as hubby)
Both love good food and comfy (but not extravagant) lodgings- think B&B. Both very curious about the Ponte Veccio. (sp?)

Any advice re: itinerary, buying tickets, points of interest, lodging, etc.? Any and all comments welcome and appreciated!

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