Sailing Destinations on the Chesapeake Bay for a Relaxing Escape

chesapeake sailing destinations

Top sailing destinations on the Chesapeake Bay where you can relax, explore and drop anchor while avoiding crowded anchorages on the bay

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If you read national sailing publications, you might come to the conclusion that the Holy Grail of chartering is the Caribbean. However, the Chesapeake Bay is a beautiful, marvelous, and occasionally challenging venue for chartering.

My knowledge and experience primarily covers cruising by sail. That being said, I know there are also at least a few charter and rental businesses which provide power boats for intervals of hours to days.

The Chesapeake is a deceptively large body of water. It runs 200 miles from Havre de Grace, MD at the mouth of the Susquehanna River to the twin capes in Virginia. It is as narrow as 3 miles across up north and as wide as 25 miles in the lower end. While notoriously shallow in some of its prettiest creeks and coves, its deepest point is 200 feet south of Bloody Point on Kent Island.

Those inclined to explore will find nearly every navigational circumstance they might imagine. Furthermore, one could write a full thesis on the weather and attendant surface conditions on the Chesapeake Bay.

My preferences tend toward smaller, less populated anchorages. I sail for relaxation and respite. I seek tranquility in lieu of cacophony and discord. However when conditions are more conducive, I will cruise into towns like Baltimore, Annapolis, and St. Michaels. That is usually in early spring or late fall when the weekend parades of boats across the bay have subsided.

Where does Capt. Rob like to go for quiet restoration? I will be happy to share a few of the destinations I frequent.

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Magothy River

I keep my boat in Rock Hall, MD. I typically only have 2 or 3 day weekends to create the experiences I enjoy so much. Having a reasonably short run to the night’s anchorage is important.

Since Baltimore Light is only 8 NM from G”3” marking the southern tip of Swan Point Bar, the Magothy River is our most frequented overnight destination. The most popular anchorage on the River is on Sillery Bay north of Dobbins Island.

magothy narrows

I usually find a significant number of power boats anchored or beached on the north shore of Dobbins Island. By sunset, most gather their things and leave. One should be mindful of the shoal on the west side of Sillery Bay. It is not passable except by jet skis, small daysailers, and other vessels of similarly shallow draft.

Sillery Bay
Sillery Bay

If one gets there and finds the anchorage too crowded, try heading through the Magothy Narrows to anchor in the cove between Holland Point and Purdy Point. The rolling horse farm to the north provides a pleasant vista. The area to the south is unpopulated.

Some people continue past this area to anchor in Inner Harbor near the Gibson Island Yacht Club. If there is a light to moderate easterly, this can offer a nice view of the Bay at night.

Magothy Narrows and Gibson Island anchorages

If you are looking for just a bit more privacy and isolation, try heading further up the Magothy to Broad Creek. I like to anchor near where there is an “M” on the chart in 8-11 feet of water. This is a good hurricane hole. There are high banks on both sides and there are usually very few boats in here.

Broad Creek off the Magothy River
Broad Creek

I would avoid going all the way to the head of the creek where there is still 8 feet of water without having at least a little local knowledge. In any event, pay close attention to the private markers in that part of the creek.

Tilghman Creek

After a long day heading to St. Michaels, you might not want to push into the harbor if you can’t get a berth for the night. This would be especially true if are not coming through Kent Narrows.

Tilghman Creek
Tilghman Creek

Just around Rich Neck on Eastern Bay is Tilghman Creek. At the head of creek is the small town of Claiborne. There are a few workboats there. Along the creek are a few homes. Despite the appearance of adequate room, you will not want to anchor in the creek proper to avoid interfering with the watermen leaving early in the morning.

My preferred place to drop a hook is in the first arm of the creek to starboard once you pass the last entrance daymark. There is room for 3 or 4 boats in that little cove. If you are concerned, the outer finger of land is short and you can use binoculars to see how many boats are already in there before you make the approach.

Note that on your way to the first entrance mark, leave a good distance from the G”1” before you turn south into the entrance channel. The outer daymark sits in very shallow water. Then you will want to stay in the middle of the channel until you clear the last of the channel markers.

Harness Creek

If you have spent the day cruising off of Annapolis and you want a quiet spot to spend the night away from the hubbub of the Sailing Capitol of America but still close nonetheless, I can recommend Harness Creek.

Harness Creek and South River
Harness Creek and South River

Harness Creek is on the South River. Head south of Thomas Point Light and follow the navaids into South River. The entrance to Harness Creek is south of Persimmon Point. There are not any convenient marks to identify the entrance so you will have to rely on your pilotage skills.

The best place to anchor is the small indentation in the shoreline straight ahead where the creek turns sharply to the left. Depths range from 8 to 11 feet and the high banks around the small bight provide a secure and safe anchorage.

So many other places…

I have cruised the entire Chesapeake Bay from Havre de Grace to Norfolk and Cape Charles, VA. These are just a few of my favorite overnight stops.

There are dozens of beautiful creeks, coves, and rivers to draw you in. Pick up your chart. Look around. Explore. Take a chance. And get your anchor dirty!

The Chesapeake Bay is a gorgeous estuary full of history and natural resources. One can find ways and places to enjoy the Chesapeake for years to come.

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Capt. Rob Chichester

View posts by Capt. Rob Chichester
Capt. Rob is an engineer and owner & operator of Chesapeake Flotillas offering charters, instruction, and vessel relocation. A USCG Licensed Master, Capt. Rob has planned and executed flotilla cruises all over the Chesapeake Bay, Europe, and the Caribbean. Rob holds a 200-Ton Master's license with Auxiliary Sail and Assistance Towing endorsements. He also is certified by the American Sailing Association to teach Basic Keelboat Sailing, Basic Coastal Cruising, and Bareboat Chartering. A self-proclaimed sailor & poet, he operates a 41-foot sloop Bay Poet based out of Rock Hall, MD. Rob has also trained and served as captain of tall ships including the state tall ship of New Jersey, the Schooner A.J. Meerwald.
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