Re: First time on the Chesapeake
You will love the upper chesapeake bay! Lots of things to do and neat places to check out! I try to get down there as often as I can but have to admit that it is not as often as I would like!
If you are staying in Perryville, you will be close to a bunch of stuff. Good location!
You can check out this thread which has answers to a lot of your questions about restaurants, wakeboarding, etc. It is a 2 year old thread which has become pretty active lately.
http://forums.iboats.com/showthread...HQAAABz3YRC&bcsi_scan_filename=showthread.php
Also, what you doing next weekend? A few of us here from iboats are getting together for a raft up near Havre De Grace. Check out this thread for more info. The more that come the better. Maybe you can get your friends to come too!
http://forums.iboats.com/showthread...3QAAACLuoVC&bcsi_scan_filename=showthread.php
As far as waterspots go, you are right on the Susquehanna river which will be a good spot to play. Stay north of Garrets Island and have fun!
As far as Restaurants go, here are a few of my favorites:
Woodys - North East - Not accessible by water

Nauti Goose - North East - On the water
Tidewater Grille - Havre De Grace - On the water
There are a bunch more around, some in Chesapeake City and on the Sassafrass River. Still trying to get to them.
I think having a VHF radio on the boat is a great idea. However, if I was you I wouldn't run out and drop a few hundred dollars on one for this weekend. Just make sure that you are with your friends and everyone is watching out for one another. However, if you do fall in love with the bay and get a slip next year. I would absolutely put one in!
It would not be a bad idea to have some charts of the area with you as well. If you are staying with friends and follow them it won't be as bad. Stay in channels and you will be fine too. But a couple charts would help if you start exploring on you own. Here is a link to an online version that you could just print a few pages of just to have. Better safe than sorry.
http://www.charts.noaa.gov/OnLineViewer/12274.shtml
Also, the book Skargo mentioned is very good as well! I would grab a copy if i were you, especially at those prices!
Hope this helps, if you need more info just ask! I will be happy to help with what I can. And there are others here that are more knowledgable then myself!