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It depends on what you like the most.
If this would be the first time in Italy then you should start with Rome and just stay in Rome for 8 days. It would be barely enough to see the city. You should start with Rome because here is where you have 70% of the cultural assets of the country. It is the capital of the country and it is where everything started. Once you have better understood Rome, the rest would be easier to understand.
If you don't want to stay in Rome for one week, then you should avoid Rome completely. Going to Rome for just three days would make you just unsatisfied. You would run all the time trying to see everything and would miss the best of it.
If you want to skip Rome then you should decide if you prefer to go North, Center or South.
Here is what you could do in 8 days, if you skip Rome:
A. CENTER: Go to Florence, spend 4 days there visiting the city, then rent a car and visit one day Pisa, one day Siena, one day San Gimignano and one day the Chianti area.
B. CENTER: Go one week in the region Marche near the sea (Senigallia, Porto Recanati, Civitanova Marche, Porto S. Giorgio), spend your mornings on the beach and use the late afternoon and evenings to tour the medieval cities in the inland (Loreto, Recanati, S. Severino Marche, Fermo etc)
C. SOUTH: Go to Naples 3 days and then rent a car and spend the rest along the coast (Capri, Amalfi etc.) and spend one day in Pompei.
D. SOUTH: Go to Sicily. Rent a place in Siracusa. Spend your mornings on the beach and the late afternoon to tour the city and the rest of Sicily (Catania, Taormina, Etna Volcano etc.)
E. NORTH: Go to Milan and spend 3 days to tour the city and then visit Brescia, Como and the cities around the lake of Como.
F. NORTH: Go to Venice, spend three days to visit Venice. Then rent a car and visit Verona, Padova, Mantova and the Garda lake.
I believe that the main problem on your original idea depends on the wrong estimation of distances and time needed to tour a certain city. In example to go from Rome to Milan would take 7 hours driving. To go from Milan to Venice it takes 4 hours driving. To go from Venice to Florence it takes 8 hours driving.
If you have just 8 days, you should optimize the time you have to get the best out of the trip.
To make your own mind regarding the places I have described above, you can have a look at this website: http://www.apartmentforrentitaly.com/
In addition to apartments rentals (which is a good alternative to hotels) this site has a concise description of all Italian regions with photos so you can make your own mind about it.
For Rome, look under Latium. For Florence, look under Tuscany. For the region Marche, look under Marche. For Naples look under Campania. For Sicily look under Sicily. For Milan, look under Lombardy. For Venice, look under Veneto.
Hope this helped.
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