You'll like Wildwood- make sure you have time to check out the museum while you're there.
Don't get a psych on about your pilotage skills, you'll get the hang of it after a few more x-cs, I bet. It's hard to use the chart on short flights close to home, sometimes... on my recent BFR, I had a hell of a time at one point getting oriented; no significant landmarks nearby, except the home airport (!), which I couldn't see because it was under us...as I circled and fumbled with the chart...

That's where ded. reckoning comes in. If you plan very carefully beforehand with a nav log showing ETAs for reliable landmarks about 20 miles apart or so, you should do fine. I've also learned to plan to fly abeam airports and other small landmarks- too easy to not know your time of passage because you can't see the thing under the nose.
Of course, you should also remember your lost procedures, which includes calling ATC and admitting you're a noob and you're lost, if necessary. They'll be happy to help and won't laugh at you- not on the air, anyway...

Another thing about learning DR and pilotage: by all means use navaids as part of it. I'll often use a radial with a visual landmark ("OK, that's the river, but which part?"); that and NDB bearings and DME info. help you learn how to follow that line on the chart without "cheating", that is, flying from navaid to navaid.
So plan carefully, fly the trip in the sim, then go have a great time!
And watch out for A-220... I don't know what they do in there, but I avoid it.