Go for it, and have a wonderful time. We are just back from 2 weeks in Sweden w a 3yr old and a 3 mo old. It was a fun -- even relaxing -- trip. My bias is always to travel light. People always get freaked out, as if other countries are uncivilized jungles where there are no baby wipes. They have babies in Italy too, so if worse comes to worse, you can buy anything you need. Although it is true that you won't find baby changing stations in restaurants. On the other hand, people are less freaked out about baby nudity in Europe, so you can change your baby more places on the fly.
For the little one, I brought a few outfits of different weights (but not too many - so I could buy a couple), a car seat (the bucket part only), a light-weight pocket sling my son loves, and a wrap-style carrier (more comfy than a sling or Bjorn since my son is huge). The wrap also doubles as blanket. In Scandinavia, women nurse anywhere without stress or hassle. But for Italy, you might wish to inquire. I was in france when my first son was an infant, and was happy to have a ring sling for ultra-discrete nursing.
On this trip I did not bring any stroller for the baby, since I'm a lite-travel fanatic (need hands for kids); but if you want one, I recommend the Maclaren Quest, which is comfortable for a child starting at 3 months, lightweight, small, includes rain cover, sturdy enough for cobblestones and tight corners and tiny Euro sidewalks. Or, a totally different way to go is a bigger, heavier Euro pram with big wheels and the carry cot, in which your child can nap and sleep at night. You can buy one of these in Europe, and they are great for countries with good handicap/ stroller accessibility (Sweden, Germany), but a nightmare if there's no infrastructure for you to get them up stairs and into buses and subways (Paris). I have no idea about Italy. In any case, don't bring something with lightweight wheels that must be pushed on a smooth paved surface, even if it works with your car seat.
If your child has any sensitivities, you may want to fill travel bottles with his or her special soaps and laundry detergents, otherwise it's fun to get euro products at the drug store.
I brought 2 lightweight blankets, one in my diaper bag at all times. The plane can be cold, and their blankets are skeevy.
On the plane, you can request the bassinet (bulkhead row only), but they can't guarantee it. They can be really mean at the airport(s) (despite many calls in advance and assurances we'd be together in the bulkhead, we were seated in 3 different sections of the plane -- me and baby -- 3 year old son -- husband; and NO ONE would help us at any step of our connections. USAir has TERRIBLE customer service. ) Take solace in the knowledge that people will be nice to you again -- very very nice -- once you are in Europe.
I try to always avoid travelling with a pack and play if possible. Just transporting it in a small European car trunk can be a headache. Our hotel and rented apartment had one, and at relatives we put baby on a couch cushion wrapped in his blanket next to our bed. If that is too sketch for you, consider one of those fold-up travel bassinets. some are tiny and cool and not expensive. Just try it out at home first.
I brought 2 packages of diapers with me (we like G-diapers) and one soft pack of wipes but that was so I had room in my suitcase for all the books we always buy!
You will have a lot more contact with people on the street than you ever would without your baby. People everywhere love babies, so enjoy!
Then most important thing to bring is your sense of humor.
Claire