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For years, we had longed to sail the Chesapeake. Comprised of waters from six states, this bay is the stuff of legend for boaters. It’s huge — the largest estuary in the country — with great ports and harbors and more than 11,000 miles of shore to explore.
My husband (and captain) Greg found Haven Charters out of Rock Hall, and Stargazer was to be our vessel for a September voyage. Never having sailed these waters, we thought we could easily zig zag, tacking across from the eastern shores of Rock Hall to Annapolis, then over to St. Michael’s, down to Solomons, and to Tilghman. We soon realized the magnitude of the width of the Bay was 15-20 miles across and sailing can take four hours shore to shore.
Provisioning and orientating ourselves to the 44’ Hunter sailboat in quiet Rock Hall harbor was efficient in this surprisingly humble hamlet. Nicknamed “The Pearl of the Chesapeake,” Rock Hall is an old-school harbor town with one basic grocery market, a CVS and a few inns. From the marina, we discovered several bikeable waterfront dining options: Waterman’s, Harbor Shack and the Inn at Osprey, a lovely historic waterfront inn where we enjoyed our last landlubber meal before embarking the next morning.
On our first day of cruising, we were immediately impressed by the sheer size and expanse of the waterway. We were also surprised at how temperate the weather was for mid-September. One moment the Chesapeake Bay is flat, calm, hot and humid, without a breath of wind, and just a few clingy gnats that descend upon your vessel. Then the wind can quickly whip up to 15-20 knots, blowing white caps up the bay, creating a 3-to-4-foot chop.
Heading southward to our first port of Annapolis, I spotted my first screw pile lighthouse. What a cool hexagonal beacon, especially for a gal from Maine accustomed to traditional towering spires. We later learned the Chesapeake once had 42 of these beautiful, raised lights throughout the Bay, but now just four remain.
We sailed into Annapolis, the heart of the Chesapeake and America’s sailing capital (Newport, RI, claims this too, but Marylanders say Newport is not a real capital). We sailed past the breathtaking sight of the bright blue and gold sails of the Naval Academy fleet. The waterfront of this beautiful port city is filled with moorings and marinas. We soon found our tight well-protected slip at Annapolis Yacht Basin and maneuvered a successful inaugural docking in the posh Annapolis Yacht Club.
Annapolis is full of fun attractions for sailors and sea lovers, so we stayed for two nights. On our first evening, we strolled across Spa Creek Bridge to an anniversary dinner at Carrol’s Creek Café overlooking the harbor. We enjoyed our first delicious Maryland crabcakes of the trip with bubbly. That evening back on Stargazer, we were serenaded to Taps played at the Yacht Club at dusk, a salute to the end of the sailing day at this traditional yacht haven.
Our full day of exploring Annapolis started with “The Star-Spangled Banner” resonating across the harbor from the academy. After a fabulously filling breakfast at Chick & Ruth’s Deli, we walked to the Naval Academy for a scheduled tour.
The glorious Naval Academy grounds, The Chapel and Bancroft Hall, where 4,500 cadets are housed, are all magnificent. To witness the uniformed “plebes” (freshmen) on campus and the midshipmen marching to class around The Yard in an orderly fashion is awe-inspiring. They performed noon formations in front of the towering granite Bancroft Hall. These bright selected-few are diligently training to become U.S. Navy and Marine officers, a ritual that has continued here since 1845.
Maryland’s State Capitol was next on our walk. This grand 1772 state house towering above the harbor served as the U.S. capital for nine months in 1783. Among other poignant moments, George Washington delivered his resignation here. The Declaration of Independence and Bill of Rights were on display in their original formats.
Just strolling the historic streets of Annapolis amid colonial architecture of beautiful homes, inns and shops, is pastime enough. Ego Alley along the waterfront on Compromise and Dock Streets is highly entertaining, especially to watch visiting boaters tie up. Always more fun watching others dock, right?
Craving more Maryland crab, we dined at The Boatyard in Eastport, across the Spa Creek Drawbridge. We decided their slogan “All killer, no filler” is sassy but true as we savored delicious crabmeat.
After our feast, a trip back in time walking the quiet streets of Eastport brought us to the Annapolis Maritime Museum on Back Creek. In a former 1886 oyster plant, we learned the tradition of local oystering and crabbing in the Bay where oysters are the “Pearl of the Chesapeake.”
From the late 1800s to early 1900s, the oyster harvest here was larger than any other source. These huge yields eventually depleted the oysters that are vital to the health and cleanliness of the Chesapeake. We learned that one oyster filters 50 gallons of water daily, that’s why oyster beds are called the Bay’s “white gold.” Today, oyster production is rebounding, and the water quality as a result, but oyster yield is still about 1% of what it once was. Crab yield and production is also challenged by a labor shortage as it’s hard to find workers for the tedious task of handpicking crab meat from the shell. Made me appreciate my Maryland crab-eating tour even more.
To cap off our time in the sailing capital, drinks at Davis’ Pub on the water in neighboring Eastport seemed fitting. This local dive bar by the Back Bay is famous, fun, friendly, cheap, and loaded with boaters and memorabilia.
Sailing out of Annapolis, I was melancholy to leave such a happening and historical place, but St. Michaels across the bay was calling. Making our way past big container ships, fishing vessels, ferries and the big wakes they created demanded our full navigational attention.
St. Michaels is a delightful harbor, on the Chesapeake’s Eastern Shore. We had reserved ahead to dock at Chesapeake Bay Maritime Museum, where we joined as members for a discounted slip plus a tour of the boat-building facility and Hooper Strait Lighthouse.
Stretching our sea legs, we walked the tree-lined blocks admiring flowering gardens, graceful porches and charming homes from the 1700s and 1800s and headed downtown into St. Michaels. Talbot Street is the prettiest slice of Americana, with inviting boutiques (love The Preppy Redneck), restaurants, a distillery, two wineries, a brewery, car museum and the impressive St. Michaels Church.
Foxy’s Harbor Grille along the harbor was perfect for a crab and rock fish lunch, along with happy hour drink deals that added to the fun tropical vibe. A local band was slated to play on Foxy’s deck overlooking the marina.
Theo’s sign “Shorts and boat shoes welcome” persuaded us this was the place for a casually elegant dinner in town. It’s a steakhouse, but the BBQ shrimp appetizer was amazing, followed by Theo’s best burger. The bar was lined with locals for happy hour; always a good indicator.
After a wonderful night sleeping aboard Stargazer, breakfast in town at Carpenter’s Street Saloon provided a yummy throwback of buttery homemade omelets and hash browns in this converted 1887 pharmacy.
Leaving St. Michaels was hard, but the promise of another port — this time the reputed party atmosphere of Herrington Harbour Marina — was next, back across the Bay to the west.
Herrington Harbour South is a narrow inlet loaded with boats and 600+ dock slips. Ours included access to a beach, resort pool with a bar and Ketch 22 restaurant. The full-service marina also offered a small market for provisions. We sat on the beach overlooking the Bay, then jumped into the pool party atmosphere. That evening, a big wedding provided music, proving that Herrington is as billed — fun and festive.
The next day, we continued south to Solomons Island. A rare wind from the north pushed us along the scenic Bay’s western shore into the Patuxent River then Back Creek, where we found Spring Cove Marina. Dockhands greeted us and tied up expertly, welcoming us to enjoy the poolside Wheelhouse bar and the ship’s store. A quick dip, refreshing showers and laundry, and then we were excited to borrow courtesy bikes to explore the island.
Calvert Marine Museum was a quick pedal from the marina. This impressive maritime exhibit and aquarium hosts the 1883 Drum Point Lighthouse, another screw pile design we eagerly climbed. It seemed apropos to lunch at The Lighthouse’s big waterfront deck. More delicious crab paired well with the local libation, a sweet but boozy Orange Crush cocktail.
We biked along the riverwalk and out to the southern tip of Solomons, stopping on our return to reserve dinner at Charles Street Brasserie. At that cozy French bistro, we shared creative tapas amid piano entertainment. Perfection.
While leaving Solomons the next day and heading back north, fighter pilots swooped overhead from Patuxent Naval Air Station, testing the latest military aircraft at Trapnell Field. Another exciting salute!
Tilghman Island across the Bay to the Eastern Shore was our final stopover and a two-night stay at Knapps Narrows Marina, as my captain eyed the forecast of thunderstorms. Fortunately, Tilghman is an adorable seafaring town with happy locals on both sides of the Kent Narrows Bridge, which they claim is the “busiest drawbridge for boaters in the United States.” This was hard to fathom in such a peaceful place.
While the sun was still shining, we enjoyed the marina pool, then hopped on bikes to ride over the bridge to the Tilghman Island Country Store. It felt good to ride, so we continued passing verdant soybean fields out to Black Walnut Point and Bar Neck Road. You actually can bike all the way to St. Michaels, Oxford and Cambridge, with more time and more promising weather. We spied “Two If by Sea” on our route and returned for dinner in the only place open on a Monday. This funky diner featured open-mic that night. Our evening was a hoot, featuring homey food and local talent.
Tilghman Day Two was as wet and wild as predicted. Over our leisure continental breakfast at the marina, we chatted with fellow boaters also staying put for the day. Good books and relaxing on Stargazer was a fine way to while time away.
Fortuitously, the skies cleared, and a double rainbow appeared in time for our much-anticipated dinner at Tilghman Island Inn. This surprisingly chic restaurant is incongruous in the otherwise bucolic town. The chef ’s fabulous crab cakes and fresh fish remain a trip highlight, along with the evening sunset and rainbows after the storm.
The entire voyage, I felt fortunate that my captain had carefully planned an epic Chesapeake charter aboard Stargazer, taking random luck out of the equation. On our maiden Maryland voyage, we had feasted sufficiently on crab dusted with Old Bay, sailed and biked, and visited six fascinating ports, leaving dozens more to explore on our next Chesapeake adventure.
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