There is not really anywhere to stop once you hit the Ocean from either direction. Both directions have their merit. The Northen Bay requires heading out through the Canal and into the Delaware Bay. The Delaware Bay can be very crowded with large barges and the tide creates a wicked current. You generally will have to motor through the Bay just to avoid the shoals on either side of the channel.
The Southern Route is more pleasant and there are many opportunities for anchorages until you hit the Ocean.
When you get to Ocean City respect the Channel Markers when you get through the Inlet as the Assawoman Bay is very shallow. How long the trip takes is really dependent on how you plan to proceed.