This short guide of sailing Chesapeake Bay is designed to help cruisers who may be on their first trip. It doesn't cover all the places to stay or see but instead tries to give you an idea of an easy way to travel this area if you don't have lots of time for sightseeing.
Chesapeake Bay runs about 160 nautical miles from the west end of the C&D Canal to the Norfolk Harbor entrance. We have stopped and “smelled the roses” in several areas but our trip through here typically takes 4 on-the-water days. As the bay runs mostly north – south, any day with big winds from either of those directions can make for a rough ride. We typically sit out those days at one of the many excellent anchorages.
Our trip down the coast of NJ from Sandy Hook usually ends 32-34 hours later in the Sassafras River. There are some excellent anchorages on the Sassafras where we’ve sat out big storms for several days before continuing. The best anchorage is about 5 miles in around the “S” turn. You can anchor far enough off the channel so the powerboat wakes are not too bad. About 10 miles in from the bay on the Sassafras is Georgetown, MD. Georgetown Yacht Basin is a good place to relax at the dock and they have an excellent ship’s store and a large boatyard if you need work done on the boat. They also have a free loaner car which makes restocking easy from the nearby mall. Across the river is Sailing Associates where we spent a few days last Fall. It is a quiet marina with friendly staff and a nice pool.
Our first day down the bay runs from the Sassafras to Annapolis. Any winds but south make for a nice sail. We would leave at sunup so we could be in Annapolis in the afternoon and get a chance to go into town. We almost always get a mooring from the city marina ($35 / night). There are many moorings right in front of downtown with easy access to the dinghy dock. East to southeast winds can bring in a swell off the bay which can make this an uncomfortable place. If the forecast is for winds from those directions, we instead go into Back Creek all the way to the end near Bert Jablin’s Yacht Yard. There are 5 or 6 city marina moorings there which are protected from any wind direction. Sometimes there are no moorings available (like in September around the boat show) so instead we would go up the Severn River a few miles to Weems Creek. This is a nice, protected anchorage with a dinghy dock near the bridge for easy access to a few restaurants, grocery and liquor store.
Annapolis has a lot to offer for cruisers and we love walking around the downtown area. One of our favorite places to eat is Chick and Ruth’s Deli - awesome burgers and milkshakes. You always see Navy Cadets walking around town in uniform and we’ve stopped to talk to them several times.
Leaving Annapolis heading south our next stop is usually The Solomons with excellent anchorages and a few places to get ashore for groceries or lunch. This day is about 45nm of fairly open water so we would only go with winds under 15-20 knots and not from the south. The course is pretty straight forward down the open bay.
The Solomons have several rivers / creeks with protected anchorages but we usually go up Back Creek and anchor in the open area just south of Anglers Pub. They have excellent lunches and we were there one evening for dinner when they were having a Bar Trivia contest. We ended up teaming with another couple who complimented our knowledge (they were good at movies and sports) and we won second place. Lots of fun….
Day 3 we would sail another 50nm to the Deltaville area. One of our favorite anchorages is around Stove Point into Fishing Bay. Lots of anchor room here and excellent holding with protection from almost any wind direction. Fishing Bay Marina is easy by dinghy and offers a “visitors pass” for transients – I think they were $10 each. You can use all the marina facilities including the loaner car (somebody else was using it the day we were there) and bicycles.
From Fishing Bay, you need to pick decent weather for the run the Norfolk. It’s only about 40nm but it is the most open part of the bay. Two or three times we’ve left here for the sail south only to turn around and come back when the winds were too high or from a bad direction which made the sail uncomfortable. In nice conditions, it is a beautiful sail and I always look forward to entering the protection of Norfolk Harbor at the south end of the bay.
Once again, we typically try to leave Fishing Bay early enough to make Norfolk by early afternoon. We like to get through the Gilmerton Bridge (first ICW road bridge that needs to open for us) before their rush-hour lockout that runs from 1530-1730 Monday thru Friday. If you can’t make Gilmerton before 1530, there is a good anchorage at Hospital Point where the ICW starts. We don’t usually anchor there because many of the powerboats don’t care about the no-wake zone and it can get lumpy.
Sailing past the Norfolk Navy Base is one of the highlights of the trip south. It’s awesome to see the huge carriers and front-line war ships at the docks. I’m always looking up ship names on the Internet when we go by so I can what they do.
Once through the Gilmerton Bridge, we stop at Top Rack Marina for fuel and sometimes stay overnight if it is late. They usually have some of the cheapest fuel on the ICW. Dockage used to be free is you ate at their restaurant but now it is $50 / night. The restaurant has excellent food but a little pricey. There are no other stores or restaurants in the area withing walking distance from the marina.
If we have enough time after fueling (or the next day) we motor the 3-4 miles to the Great Bridge Lock. Southbound boats enter on the ½ hour. Traveling south, prepare to tie up on the starboard side and you don’t need to put out fenders since there are rubber strakes built into the lock. You should have two fairly long (40’) lines ready with one tied to the bow cleat and the other tied to the stern cleat. The lock tender will take each of your lines with a boat hook, run it around a cleat at the top of the lock and hand it back to you. Don’t tie off this end because the boat is going to move up or down! Hold on to each line until the lock completes its cycle. The north side of the lock is tidal waters and the south side is not. The south side water level changes with the wind direction so you never know if you are going to go up or down but, heading south, you typically go up.
Once through the lock there is usually a short wait for the Great Bridge Bridge to open. On both the east and west sides of the Great Bridge Bridge are free docks where boaters can tie up for 48 hours (but we’ve never seen anybody here checking to limit your stay). The east (south) side has nicer docks and a visitors’ center with excellent walking trails. We always try to go through the bridge and tie up near the visitor’s center. This is a great area to stay a few days with restaurants, fast food, groceries, a mall and Ace hardware within easy walking distance. If you need work done on the boat, the Atlantic Yacht Basin (across the canal) can handle almost any job and they have a good size ship's store. One time we had to have the boat hauled out of the water there because something in the water dinged our propeller. They were very professional.
