I just returned from a trip to Tuscany/Umbria/Venice (as well as Spain) and have to say that it was great, and a nice break from feeling restricted (or just the monotony) at home. Towns were lively, yet not overpacked as in previous years, and every town we visited had great energy and feeling to the public places!

Everyone seemed generally well behaved with masks, etc. except if you seek out the throngs of young people at 11pm in the rowdier parts of cities.

Go if you can! The plane is probably one of the safer places to be if you're going to be among people anyway -- everyone generally vaccinated or with negative test result, and fresh air circulating as the airlines are totally aware that this is a requirement these days. Don't let the flight worry you!