cassy..
We were longtime slipholders at Skipjack Cove until we decided to build a house down that way. Several others here are still active slipholders and I'm certain they will give you their $0.02 as well as those at other marinas on the Upper Bay. My comments pertain only to SJC.
IMO, SJC is one of the cleanest and nicest properties on the Upper Bay and the Sassafras River is the prettiest tributary you will cruise on. SJC is clean, well kept and has all the amenities short of a beach. The large pool, high on a hill with an incredible view of the Sassy negates any thoughts of missing a beach. The main bathrooms have multiple "private" bathrooms with toilet, sink and shower which are clean and air conditioned. The management does (for the most part) monitor the grounds and the slipholders well. The restaurant, Signals, while lacking some ambiance (sp?) does offer a diverse menu and the crab cakes made by the manager, Steve, were recently listed as one of the Best of the Bay by readers' voting in Chesapeake Bay Magazine. Finally, the Sassy has several great anchorages within easy reach of the marina including the infamous "$1.98 Beach", so named because you can get there on just a $1.98 worth of gas (maybe $3.98 in today's price). Also, Lloyd's Creek, Back Crrek (behind Knight's Island)and Ordinary Point offer safe anchorages with clean, nettle free water. A bit further away and south, around the point at Betterton, is Still Pond Creek... but don't tell anyone... our secret!
Ok, that was the good stuff. Now the less than stellar things, again, IMHO. While the fuel dock is easily accessable at SJC, the price of fuel there is rarely a bargain. They used to offer a 5% discount to slipholders... no more. They charge for pumpouts at the fuel dock.. was $5.00 but someone else will need to confirm if that's still the cost. Pumpouts at your slip are only accomplished during the week by the dock staff with a portable pumpout machine, must be scheduled in advance and they ain't cheap! $25 seems to stick in my mind. I was never a fan of the service department at SJC due to the attitude, apparent lack of a really great mechanic and cost... the first time I used their service department was the last time. Fortunately, Duffy's Creek Marina is next door and, IMO, has a very good and affordable service department. Finally, while the management of SJC can be applauded for keeping the place in top shape, that same attitude does limit the slipholders' freedom somewhat. For an example, if you want to have a dock box you must rent it from SJC. This keeps the docks clean and looking uniform so I never had a problem with it but that does bother others. If your slip area gets sloppy you'll hear from management. That's just an example but, IMO, these things help everyone enjoy the place.
Well, I've used enough bandwidth on this and other will chime in with more info on all the Upper Bay choices, so, standby. I'll just close by saying that you need to take a roadtrip for a weekend and visit places like Georgetown, Rock Hall and Kent Island. You'll see not only a wide variety of marina choices but, also, why so many of us have found our way to the Chesapeake Bay and never regretted not looking back.
Enjoy!