On the occasions when I go in to see a doctor I park in the suburbs and take the T in. When I go to the airport I either take commuter rail or family or a friend takes me. I never drive in Boston...and I didn’t when I worked there either.
I do not mind driving on the weekend. Although the traffic on 128 is always busy.
When I went to Fenway (once a year) I take the Pike in. Get off at the Prudential and park right under the Sheraton right off of Boylston. It is about a 15 minute walk from there.