What are people's thoughts on insurance, both travel insurance and/or medical insurance for first time traveling to Italy?
Have you searched this forum for info on Travel Insurance?
Be sure to use the filters n search for Type and Date.
That said we always travel with insurance that fits our needs- (everyone's needs are different.)
Yoou can use insuremytrip.com to compare inclusions and plans
Check your work provided insurance -- when I worked mine covered care abroad and also airlift home. My medicare medigap policy covers 60K of emergency care abroad BUT not airlift -- so for years we had an additional Medjet Assist policy. The thing most likely to bankrupt you is high medical costs and particularly cost for airlift home. A friend's family had to mortgage their home to get their child home from Egypt when she was hit with a car and had not travel insurance.
I wouldn't worry about luggage or airfare costs -- but medical costs are important. We had an allianz policy when I broke an elbow and it paid the hospital and for follow up care so I didn't need to interrupt my 10 week trip mid way -- saved them money and my trip. We now have an annual policy which I hope to never test -- but my experience with Allianz before left me with some confidence they will be there if needed.
It is a lot cheaper to get an annual policy for airlift home than a full travel insurance policy so I would not get the latter unless you don't have any emergency coverage in your current health insurance.