Summer Weekend Itineraries on the Middle Chesapeake Bay

Ideas for Cruising Sailors for Exploring the MIddle Bay

There are so many ways to enjoy sailing on the Chesapeake, from daysailing to buoy racing or point-to-point regattas. But nothing is quite like a weekend of cruising to multiple ports to enjoy the wonderful historic towns filled with great restaurants, bars, and incomparable charm.


Cruising sailor Steven Toole anchors his sailboat Hot Pepper behind Gibson Island on the Magothy River off the Chesapeake Bay.

Here are three weekend itineraries I’ve sailed in the past year on my J/120 Hot Pepper, starting from our home port on the South River. Although these itineraries start and finish at my home port, feel free to substitute the South River for Annapolis, the West River, or whatever your Mid-Bay home port is; or make the South River a new destination for you. The sequence of these itineraries can certainly be rotated depending on your starting point.

Itinerary 1: South River - St. Michaels - Rock Hall

The South River can be deceivingly challenging, with shoaling on both shores coming straight out to the channel in some spots. Tacking in the narrow river will surely give you and your crew a good workout, so be sure to gauge your crew’s participation interests if the wind direction doesn’t allow a straight shot through the channel. Two marinas and restaurants provide a destination at the Solomons Island Road Bridge, in addition to numerous placid anchorages in the creeks along both shores.

From the mouth of the South River, it’s smooth sailing across to Bloody Point, but mind the shoaling at the mouth of Eastern Bay, coming out much farther than you might expect. The depth drops quickly from the shipping lane to the mouth of Eastern Bay, from the 40s to the low teens and single digits in mere minutes.

Sailing up Eastern Bay to the Miles River is breathtaking. Be on the lookout for bald eagles overhead, which you’re almost certain to spot along the way. Also take note of the Bay Bridge center span towers peeking above the northern shoreline of Eastern Bay, which is always a peculiar sight to see. Make the right turn into the Miles River to head south to St. Michaels, but mind some shoaling midway down the river as you approach your destination.


The author at left and crew enjoying orange crushes at the Harbor Shack in Rock Hall, Maryland, after sailing from St. Michaels via Kent Narrows. Photo courtesy of Steven Toole

If you haven’t cruised to St. Michaels, you don’t know what you’re missing. The Chesapeake Bay Maritime Museum (CBMM) is worth the trip alone, so make sure you allow time to wander the grounds and take in the exhibits there. You’ll see what it was like to live and work in the Hooper Strait lighthouse, one of the Bay’s few remaining screwpile lighthouses. CBMM is also a working boatyard, where classic and historic vessels of the Bay are brought back to life or recreated by the crew of volunteer craftsmen and women within public view.

CBMM also provides overnight docking with showers, as do several other marinas in the harbor. Across the harbor is the Inn at Perry Cabin, made famous by the main wedding scene filmed there for the 2005 movie, “Wedding Crashers,” starring Vince Vaughn and Owen Wilson. Dinner at The Crab Claw is a must if you haven’t ever experienced picking crabs dockside while watching the boats come and go.

A two-block walk to Talbot Street in town offers several quaint bars and restaurants such as Carpenter Street Saloon and Eastern Shore Brewing on the southern end of town on Talbot. Don’t forget to cap off the evening with ice cream at Justine’s. Make sure you have all the provisions you need, as there is no grocery store within walking distance from the main strip in town.

The next day is a straight shot back up the Miles River, through Kent Narrows to Rock Hall. Mind the tidal charts through the narrows, as it can be impassable for any vessel drawing more than four feet at low tide (deeper draft boats must go back down Eastern Bay). The current can be quite strong at the narrows, so be sure to keep your distance when idling to wait for the drawbridge to open.

Stay close to the channel markers on the north side of the bridge as you make your way through the Narrows and into the mouth of the Chester River. Continue north along the eastern shoreline, keeping within green cans C1 and C3 to make the right turn at R4 into Rock Hall Harbor. Pay attention to the day markers in the harbor, as the middle of the harbor is all shallow. North Point Marina is on the immediate port side as you enter the harbor, offering transient slips, refueling, a pool, and showers. Gas grills and a lovely covered dockside picnic area provide the option of onshore cooking and dining right at the marina.

A short walk to Harbor Shack provides a menu of Bay favorites and often features live music on weekends, but if you want to pick crabs it’s a longer walk to Waterman’s Crabhouse unless you dock on that side of the harbor. The town of Rock Hall itself is equally quaint and charming, but you’ll need good walking shoes to get there from the harbor. The return trip to the South River sends you under the Bay Bridge, completing the circumnavigation of Kent Island.


The J/120 sailboat Hot Pepper docked at the Chesapeake Bay Maritime Museum in St. Michaels, MD.

Itinerary 2: South River - Oxford - Cambridge

Allow for extra time to get down to the Choptank around the southern tip of Tilghman Island. You may be able to dock at Tred Avon Yacht Club (TAYC), particularly if your home club has affiliate privileges there. (You may also anchor off the Strand if you have a dinghy). The town is delightful and easily walkable from anywhere you may dock. Friday nights feature club racing right off the point at TAYC, which is fun to watch after a long day of sailing.

From Oxford, it’s a short sail farther up the Choptank to Cambridge. The municipal marina provides very affordable overnight dockage with comfortable bathrooms and showers for guests. An easy walk into town presents an array of restaurants, bars, craft breweries, and shops as well as historic landmarks.

The return trip offers the option of cutting through Tilghman Island via Knapps Narrows, or around the southern tip of the island. I recommend taking the Narrows either coming or going, if not both.


Docked at North Point Marina in Rock Hall, Maryland, off the Chesapeake Bay.

Itinerary 3: South River - St. Michaels - Gibson Island

Another twist to the first itinerary is to cross the Bay from the mouth of the Chester River and enter the Magothy for a peaceful night at anchor near Gibson Island just past Holland Point (at Red House or Eagle Coves). To the north you’ll enjoy a picturesque hillside horse pasture while resting cozily at anchor with ample protection in every direction.

If the tide at Kent Narrows is too low for the passage through to the Chester River, sail back out Eastern Bay and up to Whitehall Bay just south of the Bay Bridge on the western shore. Picking crabs for dinner at Jimmy Cantler’s Riverside Inn just minutes further up Mill Creek is always a wise choice. A lovely anchorage just inside Mill Creek lets you hear the U.S. Naval Academy lowering the American flag to the tune of “Taps” just as the sun cast its last rays of the day on the Bay Bridge.

Whether you plan one of these itineraries or countless other possibilities the Bay offers, you’re certain to have a wonderful experience and build memories with family and friends that last a lifetime.

~By Steven Toole

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