Chartering a Boat on the Chesapeake Bay

Chesapeake Bay Chartering

Charter locations and sailing destinations to explore on the Chesapeake Bay

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I am unapologetically a sailor.  There is something so peaceful and calming about being on a boat under sail with the sunshine on my shoulders and the wind on the beam. And there is nothing more relaxing than sailing on the Chesapeake Bay.

I started chartering on the Chesapeake Bay nearly 30 years ago.  I have never grown tired of the Chesapeake.  There are dozens, if not hundreds, of destinations on the bay and all of its tributaries.

The venue from which you begin your charter adventure significantly determines where you may travel during your charter.  It also may affect how you prepare for your cruise.  I will share my thoughts on those points here.

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Havre de Grace, MD

Tidewater Marina in Havre de Grace is the charter base for Bay Sail School and Yacht Charters.  Bay Sail is an ASA-affiliated school.  Their fleet is modest ranging in size from 30 to 41 feet.

Havre de Grace and the marina are easily accessible from I-95 or US-40.  Havre de Grace dates to before the Revolution and was almost named the capitol of the new United States.  Many of the homes have an antebellum architecture and the buildings along St. John Street and N. Washington Street suggest an earlier time.  Havre de Grace sits at the mouth of Susquehanna, the headwater of the Chesapeake Bay.  It was also the farthest northern extent of John Smith’s voyages of discovery.

The nearest cruising destinations include the Sassafras River, Worton Creek, and Fairlee Creek.  Rock Hall and Baltimore are a long day’s sail away.  The marina is fully equipped and supplied.  Provisioning can be found a short drive away on US-40.  Several restaurants are within walking distance.

Sassafras River
Sassafras River

One of the downsides to Havre de Grace is that one must navigate a long narrow channel to reach more open waters of the Chesapeake Bay.  That can take a significant amount of time in adverse weather or current conditions.  Additionally, the more popular destinations like Annapolis and Baltimore are more than 40 miles away.  If those are among your intended destinations, you will most likely need or want more than a 2 day charter to better enjoy your cruise and its itinerary.

Rock Hall, MD

On the Eastern Shore of Maryland due east of Baltimore as the crow flies is Rock Hall, MD.  It is a quaint little town with a history of watermen and work boats.  Today, it is a recreational destination boasting 5 marinas and at least two yacht clubs.  In August, Rock Hall hosts the Pirates and Wenches Fantasy Weekend.

Rock Hall is a relatively short drive from Annapolis and therefore, Washington and Baltimore as well.  Philadelphia is a little farther, perhaps 2 hours.

Haven Charters offers a fleet of more than 20 boats over a wide range of size and charter rates.  A point of full disclosure: my own boat, Bay Poet, is in bareboat charter service through Haven Charters.

Whether you desire a cozy charter for 2 on a small Catalina or hosting a larger party while exploring large swaths of the Bay on a Beneteau 48, you can find a boat to meet your needs.  The boats are all well maintained and you can be sailing on the Bay less than 30 or 40 minutes after leaving the dock.

Haven Charters is based out of Haven Harbour Marina, a marina well known around the bay for its amenities and the quality of its services.  Haven Harbour has a pool, workout facilities, a bar and grill overlooking Swan Creek, and B&B accommodations.

Haven Harbor Marina

From Rock Hall, you can easily sail to Chestertown, Galesville, Annapolis, Baltimore, or any of several creeks and coves that invite you inside.  St. Michaels is close as the crow flies but it is a farther sail since the controlling depths in Kent Narrows can be problematic for deep draft boats.  Rock Hall itself is a popular destination for power boat and sailboat cruisers alike.

You will most likely drive to Rock Hall if you plan to charter a yacht there.  That is a good thing because the nearest major supermarket is in Chestertown which is 12 miles away.  There is a small grocery store and a Dollar General in Rock Hall but the variety of available provisions is limited.  Bayside Foods is fine for picking up bottled water, bread, fruit, milk, beer, wine, ice, and other such staples.  There are no less than 5 restaurants in town.

Annapolis, MD

Annapolis has been called America’s sailing capitol.  The density of boats and sailboats in the environs of Annapolis arguably support that title.  There are multiple marinas up and down the various creeks in and around Annapolis.

Annapolis is the state capitol of Maryland and the home of the US Naval Academy. It is common to hear the midshipmen on the athletic field at dawn for routine calisthenics.  That is as much a part of the Annapolis experience as are the oyster shooters at Middleton Tavern.

middleton tavern annapolis

The most dominant charter company in Annapolis is probably Annapolis Bay Charters, an affiliate of the Dream Yacht Charters global charter company.  They feature a variety of late model monohulls and catamarans.  You will find Annapolis Bay Charters at Port Annapolis Marina a short distance up Back Creek.  The nearest supermarket and other merchants are about 2 miles away on Forrest Drive.  You may be able to borrow a car or have the marina drive you to the stores.

bay bridge chesapeake
Chesapeake Bay Bridge outside of Annapolis, MD

Annapolis could easily be a multiday destination all in itself.  However if you prefer to slip away from the usual commotion of the city, you can find more serene destinations in any direction you may sail from Annapolis.  Even the popular towns like Baltimore, Rock Hall, Galesville, and St. Michaels are relatively short cruises away.

Annapolis has very congested waterways.  It will serve you well to keep a sharp lookout and to fully obey the navigation rules.  You will meet water taxis, day cruise boats, schooners, and the occasional Navy ship.  Whether it is thrilling or stressful will depend on how you handle the volume of traffic.

Solomons Island, MD

solomans islandDrum Point, which marks the mouth of the Patuxent River, is about 40 miles south of Annapolis.  Solomons Island is very much focused on yachts and yacht services.  There are several marinas and restaurants on the narrow hook of land that juts into the river.

The Patuxent is a very pretty river.  It leads up to near Washington, DC.  This was the route the British took when they sacked Washington during the war of 1812.  However, the power plant at Chalk Point just above the draw bridge at Benedict, MD comes with high tension lines across the river with an air draft of 60 feet which could limit passage of larger boats.

The sail up to the bridge at Benedict, however, is indescribably pleasant.  The channel is deep and wide.  Even with tacking, there is adequate room to maneuver upstream.

Unlike the charter venues already discussed, there are not any other significant towns within a convenient distance of Solomons Island but that could be an asset.  There are several gorgeous creeks along the Patuxent River and more as well along the Little Choptank River to the north.

A good day’s sail will let you reach Smith Creek on the Potomac River  Chartering out of Solomons Island gives one access to a little sailed area of the Chesapeake Bay.  It is absolutely worth the effort to get there.  It is approximately an hour’s drive from Annapolis.

There are two charter companies listed for Solomons Island.  One, Sail Solomons, has a small fleet likely because of the volume of chartering which occurs there.  The other, Chesapeake Bay Charters, provides captained charters of hourly or daily duration on one boat.

Deltaville, VA

The nice thing about Deltaville is that it gives one immediate access to the lower Chesapeake Bay.  Situated on Stingray Point, you can access the bay from the Rappahannock River.

Just as with the northern Chesapeake Bay, there are several rivers and creeks worth visiting, not to mention Tangier Island. Cape Charles, and Norfolk.

Sailing on the lower Chesapeake can be like sailing on the open ocean given the expanse of water there.  It can be challenging and rewarding.  Deltaville is at least a 3 hour drive from Washington, DC.  However, it is worth the effort.

Norton Yacht Charter is located in Deltaville.  Their fleet contains 4 boats likely for the same reasons as Sail Solomon in Solomons Island.

In Conclusion

The Chesapeake Bay is an expansive cruising ground.  One should make every effort to see all of it because each region…each area has its own flavor and character.

Whether you wish to explore popular sailing areas, isolated streams, or the broad stretches of the lower Chesapeake Bay, you will always find something new and different.  Do enjoy as much as you can.

If you need advice or suggestions for your cruise, contact me.  I will be happy to share my experience, thoughts, and advice.

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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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