This is where I grew up sailing. I sail the Bay every chance I get and love the endless variety it provides (even though the water isn't actually this color). It can be tame enough that I can sail my sunfish across it with no worries or breezy enough that our beamy 37 footer can make 7 knots. It's filled with plenty of beautiful coves and sheltered harbors to make crusing a dream.
One time when we moved, my family and I sailed the entire Chesapeake Bay from Norfolk to the Delaware Bay and then back to our new home port on the Middle River. We took a leisurely month to do it on our Watkins 27. It was a wonderful vacation filled with lots of sight-seeing.
Best Places on the North Chesapeake Bay
Sassafras River--One of my all time favorites. There is a spit about halfway up the river that creates a little cove with a sandy beach, a little creek, and lush vegetation. It was my very own jungle when I was growing up. There is a marina at the head of the river and I spent several years at the Girl Scout camp on the north shore at the mouth. My little cove gets very crowded on the weekends so it's best to hit it mid-week.
Warton Creek--The mouth of the river is pretty wide and gets some good wind; it's a great place for sailing my sunfish. Upstream a ways it gets much more protected, but gets shallow (and full) quickly. There's a great little restaurant called the Warton General Store tucked away that's definately worth visiting.
St. Michaels--The museum here is a must, but it's hard to get a good protected spot. If you're in the mood for a very nice (hence expensive) restaurant with very good food, try the Town Dock Restaurant (410-745-5577).
Chester River--A quaint little town called Chrisfield is up the towards the head of the river. The river's great for smaller boats as well as larger ones. The mouth is wide enough to give you great sailing and still be close to some excellent anchorages. The Corsica River in the Chester is a great protected anchorage and was just ranked one of the best in the world by Sail Magazine.
The Chesapeake Bay Boaters' Resource
