A Five-Day Sailing Cruise Up the Chesapeake Bay

Summer Southerlies Make for a Nice Sailing Cruise North of the Bay Bridge

With some summer-long weekends around holidays or a week of vacation, several ports of interest can be planned north of the Chesapeake Bay Bridge. Cruising northbound is ideal when the persistent southerly winds are in a locked pattern for many days during Bay summers.

Our homeport is Annapolis. If you are starting from other ports to the south, Annapolis can be your first leg. If you are starting north of Annapolis, you can modify your first leg and destination accordingly.

Leg 1: Annapolis to Still Pond (30 nautical miles)

Once you leave Annapolis, you steer toward the mid span of the Bay Bridge. Keep an alert ear on the VHF for any commercial shipping that may be just around the corner leaving from Baltimore and heading south out of the Bay. If all clear, cross under the Bay Bridge center span without delay as you marvel at the structural massiveness of the Bay Bridge. It is always interesting that while knowing full well that the vertical clearance of the mid span bridge section is much higher than your mast height, it is a suspenseful illusion that the mast might just touch something. We all go through this irrational sensation every time we transit under the Bay Bridge.

The destination of the first leg is a quiet calm cove on the Eastern Shore named Still Pond. This is a good place to drop anchor when sailing northbound or returning from the C&D canal and you need a place to sleep for the night. The other convenient quick stop is further up north closer to the C&D canal entrance at Bohemia River. The holding at Still Pond can be a bit tricky if you drop the hook over a grassy area.

Leg 2: Still Pond to Havre de Grace (17 nm)

The following day you will continue northbound up the Bay from Still Pond taking the west fork of the Upper Bay. The destination of the second leg is the historic town of Havre de Grace. There are some limited anchoring opportunities south of the Pulaski Highway (US 40) Thomas J Hatem Memorial Bridge. Best to pick up a transient slip in Havre de Grace Marine Center. Be aware of the local tide table. Tidal change can be an important planning variable for boats with six feet of draft or more. We had to time our departure from the slip at 4 a.m. to be at high tide and have enough water under our six-foot draft.

The fame of the city is because Marquis de Lafayette named it when it reminded him of Le Havre, France. Also the federal government authorized construction of a lighthouse on Concord Point in 1825. This lighthouse is still operational and is one of the must-see attractions to visit while there.

The navigation as you approach Havre de Grace is a dredged channel once you leave the deep Bay. Navigate marker to marker, and keep in the center of the channel until the depths open up as you near the city.

Other attractions while you stay in Havre de Grace after the Concord Point Lighthouse tour are the Havre de Grace Decoy Museum, Mount Felix Vineyard & Winery, Havre de Grace Maritime Museum, Millard Tydings Memorial Park, and Havre de Grace Promenade. If you love antique shopping, you will be tempted with the many stores you will see.

Leg 3: Havre de Grace to Magothy River (41 nm)

Leaving Havre de Grace, you will start the return trip southbound down the Bay. Some people choose a stop at Baltimore’s Inner Harbor. If you can make a transient slip reservation well in advance and don’t mind paying for the privilege of staying in a high tourist attraction location, the Inner Harbor is worth seeing.

We prefer the quiet places with less tourist traffic and crowding. South of Baltimore you’ll find the Magothy River. It is well protected and can offer many opportunities to explore it. It is full of high-value waterfront homes. One of our favorite spots to drop the anchor is behind Gibson Island. The island is private property, and landing with your dinghy is not permitted. However, sharing the lovely sunset of that day on the water with those exclusive homes is priceless. If you have time, you can explore further into the Magothy River and anchor at several locations further in.

Leg 4: Magothy River to Sheephead Cove (19 nm)

Leaving the Magothy River, transit under the Bay Bridge, and continue southbound until Thomas Point Light. Rounding Thomas Point Light, turn into the West River. Then navigate your way into the Rhode River. This river will open up into Sheephead Cove. There is a shallow sandbar island that appears at low tide in the center of this cove. There are also many shallow kayaking adventures that can be planned from your anchored position including paddling in a pond full of water lilies. If you happen to be there for the Fourth of July, they have spectacular fireworks in that cove.

You can also anchor in any of the coves you see along the Rhode River in case Sheephead is full with summer cruisers. It is a popular spot, especially on the weekends. Visiting outside of the weekend can be advantageous in finding a good anchoring spot.

Leg 5: Sheephead Cove to Annapolis (10.5 nm)

The last leg of this cruise is returning to home port from the Rhode River. With predominant southerly or southeasterly winds on the Bay, it will be a good sail back to Annapolis.

This cruise itinerary can easily be condensed to four days if all you have is a Friday to Monday schedule. Leg one would be to skip Still Pond and proceed to Havre de Grace as the destination. Then, the second leg would be a stop at Magothy River; third leg to the Rhode River; and return to Annapolis on the fourth day. On the other hand, if more days are available, then spending two days in Havre de Grace and two days in the Magothy will use four days of a week vacation. Two days in the Rhode River would also be wonderful.

Another alternative to the Rhode is the South River and Harness Creek along the shores of Quiet Waters Park in Annapolis. The park offers lovely walking, biking, and paddling opportunities. Note that the entrance to Harness Creek can shoal quickly and therefore be tricky to navigate. Proceed with caution and be prepared to do quick maneuvers from running aground in the soft Bay mud at the entrance. If you decide to brave Harness Creek, you will be rewarded with a wonderful natural setting.

~by Bassam Hammoudeh