1. What is the min. amount of days I should spend in these places for sightseeing? 
2. and is early October OK weather wise? thanks
3. what order do you think I should travel in
4. and which method?
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December 6th, 2009 at 7:10 am
Rome – Three days
Sorrento – Two days: one to visit Pompeii, one to visit Positano
Venice – Two days
Florence – Two days including a half-day side trip to Pisa
Cinque Terre – Three days including a side trip to Portofino
Milan – Two days
Siena – One day
If you’re going in early October, start in the north and work your way south. It will not still be beach weather in October, but you’d may as well hit the colder parts early.
Consider this logical order:
Fly into Venice.
1. Venice
2. Milan
3. Cinque Terre (and Portofino)
4. Florence / Pisa / Siena (in any order – they’re all nearby)
5. Rome
6. Sorrento (home base for Positano and Pompeii)
Fly out of Naples.
I think that Portofino and Positano are quite similar… it might not be worth visiting both outside of beach season. Early Ocotber will be cool in the north and warm(ish) in the south. Probably not too much rain, although the Ligurian coast can be damp at that time.
Because you’re doing so many stops it would be best for you to travel by train using point-to-point tickets. You’re not making enough long trips to warrant buying a rail pass. You can get train timetables at the link below… not all the times for October will be posted yet.
December 6th, 2009 at 7:10 am
Early October will be just fine. I would fly open jaw: meaning flying into one city and flying out of another. Rome- I recommend at least 4 days; Florence 2-4 days; Venice 2 days; Positano 2-3 days, Portofino 1 day and Cinque Terre 3 days. (You can go to Portofino during one of your days in Cinque Terre); Pisa 1 days
I think traveling by train would be the cheapest — Buy a Euro railpass. This may be the cheapest way to go.
Check for Eurorailpasses at www.ricksteves.com
Depending on your funds. hostels maybe the cheapest accommodations. It is cheaper to stay outside of Venice when visiting Venice.
Traveling between Rome and Florence is only 2 hours
Check out the train website www.trenitalia. com
I really cannot tell you from what point to start. Usually I would fly to the furthest point and work my way up the boot.
Additions: Since you’ve added Milan and Siena, I would stay also 2 days in Milan and a day in Siena
Since Pisa, Florence and Siena are in Tuscany, I would stay in one of these cities and then commute to the other cities Stay in Florence, then take day trips to Pisa and Siena
Positano is the furtherest point . I would either start from here or end here. With 2-3 days here, you can make day trips to Naples, and Capri or the Amalfi Coast.
Then take the train to Rome -4 days Check the train schedule to see where to pick up the train.
Then Florence—see Pisa and Siena on day trips
Then go to Liguria/ Cinque Terre You can make a day trip to Portofino and other little towns like San Remo I would stay in Vernazza as my home base. Then visit the other places from that point.
Then to Venice. Stay outside of Venice in Mestre and take the train in. Staying in Venice can be very costly.
Then to Milan. Fly in or out of Milan
Check out this map to locate the cities that you want to visithttp://www.big-italy-map.co.uk/
Information on sights to see places to stay, etc. in Italyhttp://www.initaly.com/regions/regions.h…
If you want specific information in Florence, Rome, Milan, etc. post a separate question for that specific city.