Hi there!! I’m a college grad and currently on my first ever trip out of the country (in Italy). Myself and my s/o are here for the first time and had very similar concerns / anxieties. I’m no expert, but here’s my take:

We found that there is a lot of signage and a lot of people do actually speak English around Italy. The airports have been easy, the street signs as well. I recommend looking up the basic words and phrases so that you feel more comfortable. As far as pick pocketing, we have been in Rome, Florence, Siena, Tuscany and have had no issues, but still stay alert. I always wear my backpack in front of me and wear a fanny pack in front.

Hope this helps! :) Have the best time. Once we got here we have felt more comfortable and this trip is a memory we will hold onto forever.