what is the best city to fly into from San Fransisco to Italy? Would like to start North work south toward Rome.. but cost is a factor and I am looking for the cheapest way to get there and back. thanks

Milan and Rome have the most direct flights from the U.S.--you'll have to check for west coast flights. You might save money by connecting through another major airport in Europe--London, Paris, Frankfurt, Amsterdam, Madrid--and by connecting you may find flights to smaller airports in Italy (Venice, Naples, Bologna, Florence). Try kayak.com.

It looks like "best" = "low cost"? Even with this simplified definition of "best", the answer changes day by day.

You have to probe several sites over a period of time to get what you need. Don't trust what one site says as the lowest price.

Even though I like kayak.com, it does not always find the cheapest fare. For example, looking at a fare to Nice, the kayak.com price is +50% from where I live over nwa.com price which Kayak does not list.

There is no way around doing many what-ifs to get what you are looking for at the price you can accept.

Try North to South using many airline booking sites.
Then, try South to North, South to South, North to North, South to East, East to North, etc. I use kayak.com, expedia.com, travelocity.com, orbitz.com to get idea of what carriers operate the routes of interest. Then compare these independent booking site prices against what each carrier quotes taking into account the fees I need to pay.

I usually start with six or more options. Compute TOTAL cost, available time, stamina requirements, etc. You don't want to put effort saving airfare only to be hit with higher traveling/hotel cost negating all the savings you though you got. If you are traveling across summer/business season, the hotel prices difference in big cities can be 2x so it is well worth managing the sequence of visit to make the best of the seasonal/weekend/weekday price differences.

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The best deal for us turned out to be 'fly to Zurich, train to Italy'. We are flying back directly out of Venice.
For us it was $220 to $250 less per person for Zurich rather than Milan. So we get half the savings by flying in to Zurich but decided to not waste the time on the return leg.

One thing to stay away is buying multiple tickets for multiple legs of a flight. If you buy mltiple tickets and miss your connection then you you have just wasted a ticket and might end up buying a ticket at full rack rate (big $). On the the other hand, if all of your flights are on one ticket then the ticketing airline is obligated to get you to your destination as expediently as is possible. (You will get to your destination with no additional airfare cost).

Delta has SFO to Zurich for $706 all-in (Charles De Gaule - Paris is the mid point).
Delta's price for SFO to Rome-FCO is $1,185 all-in. Who knows, you might like a day or two in Switzerland.

We live in L.A. and frequently use Zurich as a gateway city, but from both L.A. and S.F. there are more non-stop flights to Frankfurt and London. There are better connecting flights at Frankfurt than London, but if you want to stop a night on arrival (especially if your flight lands in mid to late afternoon), I think Zurich is nicer. Getting back to S.F. is probably easiest through Frankfurt.

But don't forget to check Virgin's fares to London.

By far the cheapest, though not the easiest, to fly into London, then get a ticket to Italy through Ryanair or other Southwest type airlines. HOWEVER, Heathrow is NOT easy (allow 3-4 hours for change of terminals) and switching from Heathrow to Gatwick is not fun at all.

If you can find a way to fly INTO Venice, the trip there by water taxi is one of the most romantic in the world, with one of the most magical moments I have ever had traveling. IT is not however cheap.

Sure, a water taxi is not cheap - probably about 100 Euro for the trip, but people do share. However the Aligaluna ferry from Marco Polo Airport is (relatively) cheap - about 15 Euro, and gives you a nice tour around the lagoon (Marco Polo Airport / Murano / Lido / San Marco). It takeas about an hour or so. It is a ten to fifteen minute walk from airport terminal to the ferry dock - which is the same dock that the water taxis use.

Try www.momondo.com it seems to be pretty right on.