Originally Posted by Blumie
With a car, another great thing to do is a walk on the beach at sunset. One of the better places to do this is Crane Beach in Ipswich, about 45 minutes to an hour from the city. You can follow up your beach walk with fried clams or a lobster roll from one of the many great clam shacks in Ipswich and Essex.
For a scenic overlook of the entire area, climb Great Blue Hill. Its about 10 miles south of downtown on the border between Milton and Canton. There is a small ski slope that faces northwest giving views all the way to New Hampshire. At the top there is a lookout tower that has a nearly 360 degree view of the area. There are several other hilltop vistas in the Blue Hills reservation, all are short (< 1 mile) walks. There is also a roadside lookout on Chickatawbut Road in the reservation. It has a beautiful view of downtown Boston and the harbour. Unfortunately for romance, the road is closed down at about 8 or 9 each night.
http://en.wikipedia.org/wiki/Blue_Hills_Reservation