I have made this roundtrip serveral times. My Beneteau dealer is on the Delaware above Philly. The C&D is no big deal as long as you check the tide and current tables to make sure you are going with the current. You will want to ride the tide up the Delaware as well. Monitor the
VHF for traffic and canal information.
You have a shallow draft so an ovenight at Chesapeake City in the anchorage on the southeast side would be a nice stop. Or you can tie up for the night on the other side of the canal at Schaffers. Good seafood on both sides. You could also easily make it all the way in one day. When you are going with the current you will probably see at least 7-9 knots over the ground, makes the trip shorter. If the currents allow I recommend a stopover just for the fun of it.
Most of the bridges and cables crossing the canal have much more clearance that you will need, but I have had to wait for the RR bridge northeast of Chesapeake City.
You can
anchor out for the night behind the island just upstream from the C&D exit on the Delaware. I can't remember the name of the island and don't have a chart at home. There is a State Park on the island with an old fort. You can probably get under the powerlines upstream of the island when you leave, but if you are unsure go back around the island to the main channel.
Once your go further upstream, there are no really good places to stop. I personally don't like that part of the Delaware, you have to contend with current and for the most part, it is an industrial area.
Once you get near Philly, there is more to see.