Seems your set on traveling. The Delaware River is close. Trenton is as far north the shipping channel gets and there are close to 30 Yacht clubs http://www.dryl.org/
All the way to the Chesapeake. There are sailboat racing clubs regattas and races picnics, at many places on the river and there are always things for boaters to do. Philly is expensive and very churned up water because of big ships and industrial sites.
There are Marina's at Trenton, Tullytown, Burlington nj, Croydon, Riverside, Phila, and many more south of Philly. Essington is a real haven because it's behind Tinicum island. The River of course will take you to Delaware Bay, C & D canal, and over to the Chessy.