I lived in Philly suburbs for years and kept the boat on the Chespeake. Delaware River can be sailed but you are constantly at the mercy of swift current and there are very few places to anchor and spend a weekend. For a 1 to 1.5 hour easy drive you go to the Chesapeake and you have a longer sailing season, no worry about your course dectated by 3 knot current direction, huge array of anchoring in pristine nature, better over all wind, no trash alongside your boat, many more sailors.
Here are some choices heading south
Northeaset River- quite friendly inexpensive yacht club
http://www.hancespointyachtclub.com/
Sassafras River 45 minutes to the Bay but river is long wide and sailable, a plus when its rough out on the Bay as this will be protected sailing. Lots of sailors too
http://www.sailingassociates.com/
Worton Creek- beautiful area'
http://www.wortoncreek.com/
Tolchester- next stop down
http://www.tolchestermarina.com/slips/
Rock Hall- 1.5 hours, quuint town, good reataurants primo sailing center and perfect for weekend traveling by sail. 4 hours to Annapolis, 4 hours to Baltimore, 3 hours top Worton, 4 hours to Sassafras, Chester 2 hours.
http://havenharbour.com/
http://www.sailingemporium.com/
http://www.ospreypoint.com/marina/
http://www.gmarina.com/index.php
http://www.swancreekmarina.com/
http://www.springcoverockhall.com/
Sailing on the Chesapeake is like no where else. Its worth keeping the boat there. We sail deep into November and the fall is someof the best time of the year. Not knowing what type of sailing you do and what amenities if any I just choose this small selection. It would really open you sailing horizons up from the Lake ( nice place) where you sailed before and if you choose a good place will have other sailors also and the commreadiere of that if thats important for you and your wife and family. It worth the extra drive, especoa;;y if you can go for the weekends.
Dave
