not sure if you're underway....

cape may has that 'village' feel to me.
always enjoy our visits.

food:
jackson st has fine dining. the ebbitt room in the hotel virginian, some of the best food in the area, also $$$.
next door is the mad batter, the one time best in the area, has slipped and now working its way back.
louisa's also on jackson st, seats 18 people. a long time favorite of ours. go early.

after, go to the ben and jerry's scoop shop on washington st. they're the only place i've found b&j's new flavor, schweddy balls.
rum infused ice cream with chunks of chocolate malt balls.

the bay run:

as for the run up the bay. imho the crucial part of the tidal influence begins when the bay starts to get narrow. thats where i would target the run with the tide, somewhere near the elbo at cross ledge, estimated 17 miles from the exit of the cape may canal and about 20 some miles from reedy point, entrance to the c & d. this should run you thru the canal with favorable current.