I'm planning to buy a Trenitalia "four days in two months" pass for an upcoming trip to Italy. When I try to purchase the pass online, it asks me for the first a "start date". Does anyone know...is this the first of my four days of travel, or is it the first day of the two months that my pass is valid?

Should be the start date of the two month period but usually you "activate" a pass once in Europe within six months after issue - by taking it up to a ticket window and starting the two month period. Then you have four boxes to fill in as you go along when you want the pass to be activated for that day. If any questions i recommend calling BETS (800-441-2387) who are experts in answering any questions - they also sell passes without any fees (prices: www.budgeteuropetravel.com). But Italian railpasses are often hard to realize the value of - what is your itinerary - folks doing the usual Rome-Florence-Venice trajectory don't come close to realizing price value of the pass.

Thanks for the reply. There are my travel plans:

May 10 - Florence to Cremona. Cremona to Parma. Parma to Cremona (yes, I know...long story)

May 11 - Cremona to Piacenza

May 12 - Busetto to Cremona

May 13 - Cremona to Milan

The four-day pass will cost me $198...do you think single-day, point-to-point tickets would be cheaper?

Yes i do but check prices at www.trenitalia.com and remember with the pass you still must pay for reservations/supplements on express trains ($20 for Eurostar high-speed) but you'll be taking just a few of these - most of your trains are regional trains that don't even accept reservations i believe and are also dirt cheap in a pan-European context.
Don't buy that pass until you check fares as they may well not even come close to $198.

Thanks...I thought it might be cheaper NOT to buy the pass. But...what about the "hassle factor"...isn't it easier just to get on/off the trains w/o going to the ticket windows?

Well that's certainly a factor though i suspect in some of your smaller towns there won't be much of a wait - in Florence probably - try to learn to use the automatic ticket machines. I guess it depends how much you can save by not buying the pass.

Most of these are on more local trains for which you can't reserve anyway. You could buy all you tickets at once and then just get on the next available train on the day you are traveling. I can't imagine that your itinerary will cost more than 100 euros--probably a lot less.

Just tried to get the prices from trenitalia.com

The site was a bit glitchy, but here's how I did:

Florence to Cremona - 1st: 29.93 2nd: 23.26
Cremona to Parma - 1st: 4.35 2nd: 3.30
Parma to Cremona - 1st: 4.35 2nd: 3.30
Cremona to Piacenza - only 2nd: 2.55

Busseto to Cremona: didn't show Busseto as a train stop but the distnace is less than Cremona to Parma.

System went down on me before I could get a price on Cremona to Milan, but it is a Diretto train and takes a bit more than an hour, probably half the cost of the Firenze to Cremona train or even less.

At that rate for your entire itinerary you would pay

55-60 euros for 1st class tickets
40-45 euros for 2nd class tickets

The railpass seems like an absurd waste of euros.

Wow...my thanks for all the replies. It looks like you all just saved me a pocket full of Euros. Drinks are on me in Cremona!

like ellenem says buy all your tickets at once at any station, even at Rome's airport station where lines are apt to be less and English should be spoken - but specify the date you want to use them or ascertain how long the tickets would be valid - open-ended - i think some Italian tickets must be used in a day or so but not sure so enquire about that.