Fyi - some people like to take the ferry from LI over to bridgeport.

The yale art gallery is free and very special. The pizza is good - there are a few places to go. Visit the new haven green and walk along chapel st. Maybe take a drive through some of the suburbs. Does she want to be in new haven itself or a suburb? For a birds eye view drive up the hill and look at everything from the top of the cliffs at east rock park. Its a nice city with a lot of little restaurants and coffee shops. There are many schools there besides yale, so a lot of these coffee shops are open late. Its a college town. Yet you’ll see a lot of similarities to long island because more than a few people take the train in and work in nyc - metro north goes from new haven to grand central. It has a lot of attractions and visitors, even though it is not the biggest city due to the influence of yale. She would not be too far from boston, providence, taking a drive to berkshires in northern ct and western ma or from maybe doing a ski trip to vt once in a while. Hope you enjoy your self, have fun!