Should I fly at all in the early stages and travel around Italy for 16 days or is that idea mad???

I would check with your doctor. Although you'll get some good advice here, not everyone knows your personal situation.

Well, certainly check with your doctor, but pregnant women fly every day. I flew all over the world both times I was pregnant, right up to the 8th month.

As others mentioned, make sure you check with your doctor/midwife first. In general, there should be no restrictions from airliners perspective (you'll be required to carry a letter when you fly in the last trimester).

If you get medical OK, the rest depends on how you are feeling in general, esp morning sickness and fatigue. Make sure you drink a lot of water, request an aisle seat for that frequent loo visits, avoid raw food (and others if you're on stricter American regimen). Travel plan should leave enough time to rest, and ideally have someone else schlep the luggage. Ideally find out about OB/GYN in Italy in case of emergency.

I, too, would recommend checking with your doctor. I flew last summer only 10 weeks pregnant and was so ill that I kept vomiting on the plane, in airports, etc. My poor husband spent the trip trying not to vomit himself! Had to be transported in wheelchairs. In fact I was told by the medics in Frankfurt that I absolutely could not continue on (but we did anyway as I just wanted to get to our destination and lie down). It definitely depends on how you feel. My morning sickness was extremely bad so could not eat for much of the trip. Found myself vomiting in back alleys and restaurants too. Every single place we went to we automatically looked for washrooms so I could run there if I had to. Although it did not ruin our holiday it certainly made things tricky!

Thankfully I had airsick bags from the airport handy as I definitely used them while sightseeing!

My intention is not to scare you but just to tell you what happened in my particular case. Just be cautious! Like others have said, people fly all the time while pregnant - it varies from person to person.

Double check with your MD. But, ordinarily flying until very late in pregnanacy is perfectly safe.

A different issue is if you will be at the exhausted stage where you want to sleep 12/14 hours per day (many women get this early, but many women don;t get it at all). Or if you will have morning sickness.