I am a Chesapeake Bay boater also. Here are some ideas for the Maryland portion of the Chesapeake Bay. Some of this you may know, some, maybe not. Are you a family guy or a partier? (I am guessing that you are a partier based on your boat choice.)
Western Shore:
Bush River and points north: Be careful up here, as you are entering a military firing range which is in current use! No anchoring, as there is the possibly of hitting sunken unexploded ordnance with your anchor. (Also, scraping the bottom with your boat is not recommended.) If you are going north, hug the eastern shore side of the bay to stay out of the firing range. They should have patrol boats out if the range is active, but use your GPS! (You did get a good moving map GPS, right?) You can enter the C & D canal up near the Susquehanna and go to the Delaware Bay if you are adventurous enough. Just brush up on canal rules and techniques before you go, okay?
Middle River/Back River (Essex area): The west side of Hart-Miller island at the mouth of the Middle River attracts a partying crowd on the weekends. There are one or two crabhouses which are accessible by boat in the rivers. Fuel can also be had in a few spots at one of the several marinas in the area. No single marina really stands out in my mind. Just pick one.
Patapsco River/Baltimore Inner Harbor: A great weekend destination. Highly recommended. The absolute best marina to overnight at is Baltimore Marine Center/Lighthouse Point Marina in Canton. I keep my large boat there. Very close to the Canton bar district (easy walk) or Bay Cafe is right there, where all the hotties go to scope the guys on weekend nights. (Unfortunately, I am a little too old to be scoped by any hotties.) Bay Cafe has a bikini contest weekly on Saturday afternoon. This one of the must-do events on the Bay in the summer. Fuel is available in several locations, with the Rusty Scupper Restaurant having high-octane gasoline available.
Magothy River: Anchoring out is popular behind Gibson island on the right after you enter the river. A nicely protected anchorage. Fuel up at Deep Creek restaurant (first creek on the left after you enter the river) and if you buy dinner they will let you dock overnight for free. I have taken advantage of this offer several times, since I was gonna eat and needed a slip anyway. I guess the offer still stands, I haven't actually been in a few years, but things change slowly on the bay.
Mill Creek (South of the Bay Bridge and just north of Greenbury Point): Cantler's is a good, casual crabhouse kinda place. A little tricky to navigate into, particularly at night. Definitely honor the channel markers. When you approach the river, particularly at night, the markers look confusing, but if you don't question them and just follow them, the path becomes apparent after you enter the channel. There are also the remains of a decaying pier on the south side just after the dogleg in the channel, so go slow, and scan your light if entering at night. Watch for shallow water around Greenbury point. Swing very wide and outside the spider buoy.
Severn River: My favorite river around here. Beautiful. I keep my small boat there. (Which is for sale, incidentally.) They have a ski slalom course up near the head if you are into skiing or wakeboarding. You can get fuel in Annapolis or at Smith's marina behind St. Helena Island about halfway upriver on the left. Of course, Annapolis itself is a good destination. Go profiling in Ego alley, and/or take your wife or g/f (or both) to dinner one evening. (It makes them like the boat more if you pay attention to them too.) Watch your speed around Annapolis. You can tie up alongside the seawall in Ego alley, swing on a city mooring (with water taxi service to your boat in season), or choose from any of several nice marinas in the Annapolis harbor. Hard to go wrong with so many choices.
South River: There is a cove on the right side, can't remember the name off the top of my head but I think it is the first one on the right when you enter the river, that attracts somewhat of an anchoring and/or partying crowd, depending on the mix of people, on the weekends. It is right by the park whose name I can't remember now. There are several places on the South River to get fuel, and Mikes Crab House upriver on the left is a popular crab house kinda place. No single marina really stands out on the South River. Just pick one. The water can be really choppy on the weekends from all the boat traffic. The South River seems to have more of the Formula Fastech kind of crowd. You would fit right in.
West and Rhode Rivers: More serene, with a lot of marinas on the West River and a few anchorages for overnighting on the Rhode river. Watch the water depth if you are on either side of the main channel though. There is (or at least used to be if it hasn't washed away) a small sandy spit of an island all the way up the Rhode river which was good for beaching the boat and letting the kids play in the sand and water on a sunny summer day. It was low enough that it would submerge on a high tide.
There are a couple of nice marinas around the Chesapeake beach area further south. This is more family fishing territory than Formula territory. Herrington Harbor South (not Herrington Harbor North) is the nicest marina in this area.
Next stop to the south is Solomon's Island. A good weekend trip if the water is smooth. A bit of a slog in rough water. It's a little quieter and more family-oriented in Solomon's, but there are a couple of watering holes and a coupla marinas. Or you could cruise up the Patuxent river if you just wanted to burn off some fuel, then swing on the hook overnight.
Nest stop to the South is Point Lookout where the Potomac meets the bay. It is like going camping down there. It is a little sleepy around there and not really recommended, unless you are just exploring and wanna anchor out overnight. The mosquitoes will eat you alive! There are a couple of protected coves, and St. Mary's city is just up the Potomac on the right. Again, not really much down there.
South of there on the Virginia side I don't know anything about.
Eastern Shore:
I am not as familiar with the Eastern Shore side. Here are a few tips though.
Fairlee creek is a popular dinner and overnighting destination, although I have never been.
Rock Hall is a fishing kind of town.
Sunday evening is the weekly bikini contest at Red Eye's Dock Bar at Kent Narrows. Another must-do event on the party circuit. Definitely a Formula kind of Crowd. Note that the channel markers reverse in the narrows. Honor the markers and know if you are "going seaward" or "returning from seaward." The channel is narrow so the proper path is fairly obvious, but enter the channel at the first pair of markers and STAY IN THE CHANNEL!
Fuel is available in the narrows, plus there are a few marinas. Mears Marina is popular, but any marina here would do. Just pick one.
For a family kind of weekend or to impress the g/f, go to St. Michaels, which is south of the narrows. From the main bay just south of Bloody Point, go up the Eastern Bay and hang a right. St. Michaels is not far down on the right. A little bit upscale and boutiquey, but makes for a nice weekend with the sigificant other.
South of here I am not very familiar with, although I have been to Smith Island once. Now that is like going back in time. I recommend going if you happen to be in that area. There is not really much to the place, but the people are friendly as can be, and I think you can now stay overnight. I think. They used to kick tourists off the island at dark if I am not mistaken. Also be aware that if you are down this far there is, or at least used to be, Navy firing ranges down here, so be aware of your surroundings and monitor your VHF. There was a huge ship down there that was all shot up by Navy fighters when I was down there several years ago. If you get buzzed by an airplane it is for a reason! It means that they want you to scram!
All of the above comments are taken from memory. Please search the internet for current information on or otherwise confirm my statements before you go. I highly recommend picking up a copy of the Guide to Cruising Chesapeake Bay , which is chock full of good information about every nook and cranny of the bay.
Enjoy!!
