A travel companion of nautical destination towns, sites, marina amenities, and navigation know-how for the best Bay experience this summer!
There’s a saying that “if you are fortunate to be on the water, you’re fortunate enough.” With the riches of the Chesapeake Bay watershed surrounding us, and seemingly endless options to enjoy them, this notion holds meaning and truth. We’re quite blessed in this region with access to the creeks, rivers, and bay at our fingertips. And we have a history of maritime industry, culture, and recreation to support this way of life—the Chesapeake way of living off the water and enjoying all it provides.
On the following pages, we’ll explore several destination towns that dot the bay shoreline, from north to south and western to eastern shores. These are special places that exemplify the waterfront lifestyle, have a myriad of cultural/historic sites, and marina amenities—perfect for the weekend escape by boat. We begin with…
Annapolis
What more can be written about “America’s Sailing Capital,” our state seat of government where Colonial America took shape, the U.S. Naval Academy sits, and, today, a bustling mix of waterfront restaurants, hotels, and boutique shops draw millions of visitors annually? Quite a lot.
Navigating to Annapolis by boat can be a trick, especially during peak summer season, when hundreds of vessels are cruising the mouth of the Severn River, Spa Creek, and Ego Alley at any given hour. Your first point of contact should be the Annapolis Harbormaster (hail on VHF 17 or call 410-263-7973) to get a read on conditions, the crowd, and information on dock reservations, mooring options, anchorages, pump-out services, and navigating city waters the day-of. Check annapolis.gov/165/Harbormaster in advance of departure for the latest information.
There are also dozens of private marinas, yacht clubs, and boatyards throughout the Annapolis harbor, Eastport, and Back Creek with varying degrees of slip availability, rates, and amenities. Many offer complimentary wi-fi, shore power hookups, freshwater hookups, cable tv hookups, pump-out, and even boat lifts for maintenance needs.
Once docked, the town is yours to explore. Perhaps the most fascinating development in downtown Annapolis is the emergence of a refined and quite contemporary culinary scene. Niche restaurants, gastropubs, and specialty cocktail bars have cropped up recently. If you haven’t visited Annapolis in some time, you’ll happily discover new names alongside familiar favorites. There’s no shortage of delicious table fare and nightlife entertainment.
The cultural highs of Naptown are many and have long focused on its renowned colonial and maritime history. The Maryland State House, Annapolis Maritime Museum, U.S. Naval Academy Museum, Banneker-Douglass Museum, and Historic Annapolis properties offer the most comprehensive reviews. But a renewed interest in the arts has woven visual nods to historic figures, iconic imagery, and fanciful interests in the form of large-scale architectural murals throughout the city. These colorful paintings have blossomed on buildings in town and can be found in conspicuous and obscure places—the fun is finding them and deciphering their meaning. There are at least a dozen fine art galleries, several performing arts venues, and many whimsical-to-fashionable shops in the walkable vicinity too, making Annapolis much more than a sailing town. Perfect for a long weekend or, even, a week’s stay or more!
Photo by R. Roberts
St. Michaels/Tilghman Island
It’s the town with a refined charm that hints of Martha’s Vineyard. Though locals might be shy to draw this comparison, the smalltown waterfront vibe, bucolic layout, mom and pop shops, hip eateries, upscale lodging, and elite shopping can’t be denied and make St. Michaels, and by extension Tilghman Island, a pleasure-cruiser’s paradise.
The St. Michaels harbor offers the more protected anchorage of the duo-destination, located just inside the Miles River, off Eastern Bay. If you’re visiting for the day or maybe an overnight, dropping anchor in the North or South Anchorage in the river or within the adjacent coves may be the easiest bet. From your vessel, you can hail the water taxi on VHF channel 71 to visit the town. There’s plenty of slips available, too, for longer stays. Between the Chesapeake Bay Maritime Museum and several marinas, there’s no shortage of docking amenities.
You’ll find plenty to enjoy when on land. Walk the streets surrounding the harbor and duck into art galleries and ateliers, fashion-forward clothiers, wine bars, craft breweries, and refined restaurants. For history buffs, you’ll find the Chesapeake Bay Maritime Museum’s floating fleet of vessels, expansive maritime exhibitions, working shipyard, and the 1879 Hooper Straight Lighthouse a delight.
Between the Inn at Perry Cabin and the St. Michaels Harbour Inn, Marina & Spa there are pampering services and fine dining—even golf, so bring your clubs. On most weekends during summer and fall seasons, there could be a culinary festival, outdoor concert, farmers’ market, ghost tours, sailing races, and more events. The St. Michaels Maryland Business Association (stmichaelsmd.org) has the full rundown how to get the most out of your visit.
To the south, Tilghman Island sits at the mouth of the Choptank River. The best spot to settle in is, perhaps, within Knapps Narrows—the slice of channel that creates the island proper. Private and public docks line both its sides, and there are a couple larger marinas at either end. Harris Creek is protected, also popular, and features the renowned Wylder Hotel on its waterfront. For your town excursion, we recommend hopping on your stowaway/folding bicycle to navigate between the island’s charming B&Bs, cozy restaurants, and tucked-away parks and nature sites.
Photo by Bernadette Bowman
Rock Hall
So called the “Pearl of the Chesapeake,” Rock Hall has the reputation of being a world away but with world-class amenities. True, if you were to drive by car to this mid-peninsula town, it may take quite a while to reach depending on your point of origin. But navigating by boat? Much more accessible from western shore ports-of-call—and many eastern—than by driving (just 17 nautical miles from Annapolis versus 68 by car).
On the south side of town, Rock Hall Harbor is a cove protected by massive rock jetties, and is ringed by marinas and docking, as well as several fine waterfront restaurants. The town’s north facing anchorage, multiple marinas, and restaurants in and around Swan Creek/The Haven are also protected and offer access to Rock Hall Avenue, the main throughfare. Further into town, you’ll find quaint markets, gift shops, antiques, and sundries. It’s also easy to find the party in town, as Rock Hall is known for lively events and festivals, especially on summer weekends. The Mainstay is the main draw, hosting concerts and special events regularly. But perhaps the most renowned weekend of them all is the annual Pirates & Wenches Weekend—held August 11–13th—when the town transforms into a fantastical escape to the golden age of piracy and debauchery (all in good fun, mind you). For more events and all town intel, visit rockhallmd.com.
Rock Hall also serves as the “welcoming center” to the Chester River, which is a nature lover’s passage. To the town’s south is Eastern Neck Wildlife Refuge, “a 2,285-acre island providing habitat for thousands of wintering waterfowl, including the tundra swan,” states the U.S. Fish & Wildlife Service. “Eastern Neck refuge supports a wide variety of habitats including brackish marsh, natural ponds, upland forest, and grasslands. The refuge holds the designation of Important Bird Areas by the Audubon Society. Over 240 bird species visit the refuge along with small mammals and many other wildlife species.” If you have small kayaks with you, this is the place to drop them in and tour the waters around the island, go fishing, and soak in the sites.
Havre de Grace
At the mouth of one of America’s most storied rivers, the Susquehanna, sits the wharf town Havre de Grace. Inspired by Revolutionary War hero General Lafayette, who commented that the small waterfront hamlet reminded him of the French seaport “Le Havre,” the townspeople incorporated in 1785 and adopted the name Havre de Grace. In the two-and-a-quarter centuries since, Havre de Grace has developed into an epicurean and recreational hub for all visitors to the northern Chesapeake Bay, with access to nearby state parks (Susquehanna and Elk Neck State Parks) and all manner of nature and wildlife.
Navigating to any of the marinas that line its waterfront may challenge even seasoned captains, as you’ll be crossing what’s known as the Susquehanna Flats—basically the shallower delta of the Susquehanna River with one- to four-foot depths. There are several channels up to 20 feet deep that run north to town and into the river itself. Nevertheless, the Flats are renowned for striped bass fishing early-spring through fall. Be mindful when boating this region.
Catering to transient boaters/anglers is the City Yacht Basin with more than 100 slips available, fuel, pump-out, boat ramp, angler amenities, and a restaurant (The Promenade Grille). It’s also the entry point to Millard Tydings Memorial Park and the boardwalk promenade, which meanders along the town’s southern waterfront. There are several other large marinas in Havre de Grace, ensuring options for almost every visiting vessel.
The charm of Havre de Grace is anchored to its waterfront parks, historic sites, dining, and shopping. The fully-restored Concord Point Lighthouse is a popular attraction. It’s the second oldest lighthouse in Maryland, built in 1827 and decommissioned in 1975. Within footsteps of the lighthouse is the Havre de Grace Maritime Museum and the Havre de Grace Decoy Museum, recalling the golden age of waterfowl hunting the town and region became known for in the 1800s onward. Today, boating, angling, golf, vineyards, breweries, and creameries attract visitors to town and the surrounding countryside.
At the end of a long day, respite can be found at waterfront restaurants and taprooms. St. John Street at the town’s northern end boasts a concentrated number of such places, along with shopping, supplies, and antiques. And you’ll find even more dining variety and whimsical shops just a couple blocks inland, all walkable and all within the unique, historic charm of Havre de Grace. For a complete picture of all this town offers visitors, go to explorehavredegrace.com.
Photo courtesy National Harbor
National Harbor
Prime real estate along the Potomac River waterfront with mile-long views to the heart of D.C. and its many sites—notably the Washington Monument—made Oxon Hill attractive and ripe for mixed-use development, which began in earnest during the mid-2000s. The opening of the exquisite Gaylord National Resort & Convention Center in 2008 ushered a construction wave of high-end residential and commercial properties, which in turn attracted an esteemed clientele of retail, dining, and entertainment tenants. Today, National Harbor is a luxurious townie escape, quite walkable, and boasts a waterfront replete with amenities for visiting by boat.
If you’re planning to navigate from the Chesapeake Bay proper and upriver to the harbor, several days may be required—it’s roughly 100 miles from the Potomac’s mouth to National Harbor. But good news—a world-class marina awaits. The National Harbor Marina offers weekly and long-term rates. If you’re boating from a closer Potomac-area marina, there are dock-and-dine daily rates as well. In addition to fuel, electricity, and pump-out services, the marina offers dockside delivery of provisions, private shower/restroom/laundry facilities, complimentary Wi-Fi/cable/water, and more amenities. All behind a secured gate with pin-code entrance to the docks.
Just footsteps from the marina within National Harbor’s Waterfront District are attractions aplenty. There’s a sculptural playground on the riverbank, the 180-foot high Capital Wheel, Spirit Park Carousel, and about 10 city blocks worth of high-end shops, eclectic restaurants, novelty grocers, and premium services. The entire townscape is handsomely laid out with a riverfront walkway that’s perfect for strolling the evening as the sun dips below the western bank of the Potomac.
You’re welcome to relax and stay on your vessel, but if you’re in the mood for pampering and elite service, there are several five-star resorts at National Harbor: the aforementioned Gaylord, the grandiose MGM National Harbor, the waterfront Westin, and the European-inspired AC Hotel. Among them, the MGM offers a premiere gaming floor, world-class performance theater, and its own fleet of restaurants.
While the MGM attracts big-name performers, there is year-round entertainment in one form or another throughout the National Harbor and its many properties. The Gaylord, for example, features seasonal theme-attractions, perhaps most notably ICE! during the winter. But during the summer months and into fall, it would be hard to miss the sweltering sounds of the outdoor Rock’n Raftup Concert Series, featuring live music performances on the riverfront, Friday nights from July 28th through September 8th. For a full schedule of National Harbor events, complete business listings, where to stay, and more information, visit nationalharbor.com.
Photo by Harry Pherson
Solomons
The heritage of working watermen is captured and on display at the Calvert Marine Museum and Drum Point Lighthouse—along with a stellar fossil exhibition—at the heart of Solomons near the mouth of the Patuxent River. But the real deal lives on. Solomons remains a hub for working captains of all sorts and is renowned as a charter fishing destination. The waterfront has several large-scale marinas, more than a half-dozen seafood restaurants, and a boardwalk. More information about this Calvert County destination can be found at calvertcountymd.gov.
Kent Narrows
It’s possibly the most active recreational stretch of water in the entire Chesapeake Bay, located in and around the channel that divides Kent Island from the Eastern Shore mainland. The Chester River flanks the northern shore, and Prospect Bay/Eastern Bay are on the southern side. With a dozen-plus marinas, boatels, fishing charters, and restaurants for crab-picking, sunset drinks, tiki-tunes, and live music, the Narrows is the Jimmy Buffett lifestyle close to home. Visit kentnarrowsmd.com for all the details about this 955-acre waterfront area.
Photo by Kenny Kunie
Crisfield
Located on a small spit of land tucked behind Tangier Sound near the Maryland/Virginia bay border, Crisfield is becoming increasingly known as destination worthy. Its laid-back charm, authentic seafood restaurants (jumbo blue crabs!), unique festivals (Crab Derby, Crab & Clam Bake, Oyster & Bull Roast, and Bluegrass Festival) are drawing more and more transient visitors each summer. The town’s City Dock is an extension of its Main Street, which along with Somers Cove, account for the most activity in town. Nearby is Janes Island State Park, famous for its water trails that are perfect for exploring nature by kayak. Learn more at cityofcrisfield-md.gov.
Photo by MrTinMD
North Beach/Chesapeake Beach
They’re the Chesapeake’s own “Twin Cities,” so to speak, joined at the hip by a one-mile stretch of Bayside Road. Both towns have dining, shops, boardwalks, bayfront parks, and attractions (a public beach north, a water park south). Docking is exclusively in Chesapeake Beach though, so bring your stowaway bicycles for the short ride to North Beach. Visit northbeachmd.org and chesapeakebeachmd.gov for each town’s intel.
