I commute from Kenmore Square to Norwood, the reverse direction of the usual auto traffic, and I ride early, arriving by 7:30 AM. So I travel under optimal conditions. That being said, during the nice weather when I'm training for distances, I sometimes ride to Norwood by way of Quincy and Milton. I note that no one suggested taking Morrissey Blvd. It's a wide road, and there may be sidewalks if the traffic is bad, though I personally don't ride them, and never looked. The scenery is pretty pleasant too.

I get to Morrissey through the South End via Berkley to Old Colony, to Columbia Road. Or I take Mass Ave to Columbia. At the end of Morrissey in Dorchester I either go into Quincy on the somewhat treacherous Hancock St Bridge, or take Gallivan Blvd to Adams and then into Quincy as also described above.

I then take a different Adams Street westward through Milton and ultimately back to Lower Mills in Dorchester and on to Hyde Park and Dedham, or on Centre St through to Canton and Norwood. When I'm doing a long weekend ride further down the South Shore though Weymouth and beyond, I seem to always get confused in Quincy.