Cruising the Upper Chesapeake

Every year I get letters asking where they should go on the Chesapeake Bay, so I put together a personal guide to some of my favorite places on the upper bay.

Starting from Havre de Grace, an historic small town on the mouth of the Susquahana River. Havre de Grace features Thursday night Yacht Racing that you can watch from shore. The Board Walk is an excellent place to photographic wildlife. The birds practically beg you to take their pictures. St. John Street and Union Ave provide a variety of restaurants from up-scale to burger fare. If you come to Havre de Grace be sure to stop at the Tidewater Marina and look for us. This is our home port. There are many historical buildings, the Decoy Museum, the Dock House, just lots of things to see and do.

Our next stop would be the Sassafras River. We've had many races on this lovely river. Ordinary Point offers a good anchorage with protection from storms and a small beach frequently dotted with tents. Further up the river is Skipjack Cove, an excellent marina. The showers are roomy and private and the marina has a bar and serves a buffet breakfast.

Next I'd spend a night on Worton Creek. You can rent a mooring or just anchor out. There are a couple of marinas if you need anything.

Head South past Poole's Island and then West to Middle River. That's where I took that sunset picture that everyone is downloading for there wallpaper. There are several good marinas on Middle River, we like Bowleys, the first marina on the right. They have nice showers and right next door is a Country Western restaurant that serves great steaks.

Crossing the bay again you can check out Rock Hall. This is a watermen's port, a real working port and there are several good marinas. The last time we were there we stayed at the Sailing Emporium way in the back. A very nice marina with excellent showers and a nice store. Rock Hall has several excellent restaurants and they will pick you up at the marina and bring you back after dinner. Very nice!

If your this far south you just have to go to Annapolis. After all it is "the sailing capitol of the world". You can usually catch a mooring in the basin or reserve a slip at one of the many marinas. We like Bert Jabin's on 2nd street in Eastport. It's about a mile walk into Annapolis with lots to see on the way. My crew says I don't get enough exercise.

Heading back North there is a wonderful anchorage behind Gibson Island. A good place for a romantic night swinging on the hook.

You absolutely cannot go home until you've been to Baltimore. Fells Point and Inner Harbor are right next to each other and provide great food, night life, the Baltimore Aquarium and other attractions. A great place for your last night or two.

All of these ports are within a few hours sail, only 50 miles of river from Havre de Grace to Annapolis and this "guide" represents only one possibility. It's only a days trip up the canal to the Delaware River and Philadelphia. Another trip might include Stillpond, the Magothy River, the Chester River and Kent Island. The best part is that the upper bay is well protected and you are seldom more that an hour from any port. That's an hour by sailboat. Power boats can usually make port in 15 minutes.

Come sail the upper bay. There is something for everyone.