With more than 11,000 miles of navigable shoreline dotted by dozens of charming ports of call, from Havre de Grace to Cape Charles, there are more places to explore on the Chesapeake Bay than there are weekends to explore them. Here’s a taste of some of the more popular ports of call, selected for their charm, fun attractions, and wealth of accommodating marinas and restaurants. You can start to plan your cruise with a visit to ChesapeakeBay Magazine.com and click on the “Bay Places” tab.
The charming allure of Oxford comes from the town’s delightfully serene community and waterside streets. Bordered on three sides by the Tred Avon River and Town Creek, the historic colonial port now offers visitors a museum, restaurants and biking trails bundled up in a quiet waterfront escape. While boasting several marinas, Safe Harbor, on the city’s northern point, offers boaters a chance to fuel up before grabbing a bite nearby at Capsize OXMD or Scottish Highland Creamery. Dive into the town’s storied history at the Oxford Museum and continue by putting your feet up at the enchanting Robert Morris Inn.
A highlight of Chesapeake City is that it is eminently walkable. The historic city has parks, ice cream shops, restaurants and inns. On the north side of the canal, visit Schaefer’s Canal House for overnight or hourly docking, fuel, an outdoor cafe and an indoor restaurant. The town can be described as a Victorian gem with museums, hikes along the C&D Canal, and charming small businesses such as jewelers, antique shops and galleries.
Havre de Grace
Havre de Grace is a quiet town with antique shops, interesting restaurants and unique museums. The chic Vandiver Inn stands out as a sought-out wedding venue or just as a charming weekend stay. With plenty of boat ramps, SUP rentals, and even sailing lessons, there is something for every water lover. Walk along the Layfette Trail and visit the Decoy Museum for a history lesson. Check out JoRetro Vintage as well as Bahoukas Antiques Mall and Beer MuZeum for mid-century finds. Galleries, book and music shops are all scattered among restaurants such as Coakley’s Pub, Tidewater Grille, as well as Vineyard Wine Bar for the wine aficionado, or the historic State Theater for live performances.
Baltimore Inner Harbor
From history to nightlife to activities for the whole family, Baltimore has it all. At the Inner Harbor, you can see a fleet of historic ships, the National Aquarium, restaurants, shops and even an Orioles game. Among the numerous marinas, the Inner Harbor Marina, Baltimore City Docks, Harbor East Marina, and Inner Harbor Hotels stand out as some of the most notable and most accommodating. Fun, family-friendly opportunities abound. You can get hands-on with the kids at Port Discovery, cruise the harbor, cheer on the O’s, and climb aboard the most historic ships in Baltimore, just to name some activities. For an educational approach, view Baltimore from the Baltimore World Trade Center at 30 stories, visit approximately 800 species at the Baltimore Aquarium, and all the interactive exhibits at the Maryland Science Center. When you get hungry, it’s impossible not to find something in Baltimore, but highlights include Ouzo Bay and The Bygone.
Fells Point is home to some of the most charming and lively parts of Baltimore. Keep your boat at Crescent Marina and stay at either Henderson’s Wharf Inn and Marina or Admiral Fell Inn. Walk around the old cobblestone streets, and visit the intriguing restaurants, shops and pubs filled with history. For example, The Horse You Came In On Saloon is rumored to be where Edgar Allen Poe drank his last drink. For a pub crawl, check out One-Eyed Mike’s, Bertha’s Mussels and Duck Duck Goose. Captain James Seafood Palace not only serves great food but it’s built in the shape of an ocean-going commercial vessel. Don’t miss the Frederick Douglass-Isaac Myers Maritime Museum to discover the port’s richly diverse ship building history.
Rock Hall has some of the Bay’s best sailing, cruising and paddling, along with some of the most sophisticated marinas on the Chesapeake. North Point and Rock Hall Landing are favorites. Black Duck Inn, Mariner’s Motel and Osprey Point Inn are all top-notch lodging options. Chester River Kayaks, Eastern Neck National Wildlife Refuge and Shardana Sailing Charters all offer independent sailing or paddling options. Visit the charming shopping district, including The Hickory Stick for cute accessories, The Bay Escape for housewares and decor, and Grammy’s Goodies for fresh mini donuts. More activities include the Waterman’s Museum, the pool at Bayside Park or the beach at Ferry Park. Interesting and fun food experiences include Harbor Shack for beer and seafood, Ford’s Seafood, Waterman’s Crab House and Bay Wolf. The Mainstay hosts world-class live musical performances, from jazz to classical to folk.
Annapolis & Eastport
This famed historic downtown houses the Naval Academy as well as too many shops and restaurants to count. Go for decadent brunch or fresh seafood in downtown Annapolis, and fine meats and oysters in Eastport. For casual fare, try the Boatyard Bar and Grill or Davis’ Pub in Eastport or Chick ‘n Ruth’s Deli and Sofi’s Crepes downtown Annapolis. Take your kids for a cruise on the pirate ship that tours the Severn River, then check out one of several ice cream shops along Main Street downtown. For pets, go to the Sea Dog Pet Boutique, and for the book lover visit Old Fox Books on Maryland Avenue. Tour the State House or follow the footsteps of America’s Founding Fathers as you wander the streets of downtown to learn more about the history of the capital of Maryland.
Kent Narrows might be known for its abundance of dock bars, cruising boats and happy hours that last into the wee hours, but it’s also the domain of watermen that have been harvesting the Bay’s bounty for generations. The abundance of yacht yards and marinas will leave no boater behind. As for lodging, the Hilton Garden Inn Kent Island and Hyatt Place both offer all-encompassing amenities. The Chesapeake Bay Environmental Center and Ferry Point Nature Park are great launch spots for paddlers, while SipAhoy TikiBoat will provide a captain and a waterside tour as long as you provide the beer, wine, snacks and friends. When finished with fishing off boats, or exploring the various nature parks, visit The Narrows Restaurant or the Harris Crab House for fresh seafood.
St. Michaels is one of the most popular weekend retreats for boaters, families and couples, featuring shops, restaurants, B&Bs and an elegant resort, accompanied by three marinas. For an elegant stay, visit the Inn at Perry Cabin, and for an experience with all amenities imaginable, choose the St. Michaels Harbor Inn, Marina and Spa. Notable restaurants include Foxy’s Harbor Grille and Ava’s Pizzeria and Wine Bar. The town’s crown jewel is the Chesapeake Bay Maritime Museum, where you can climb aboard the Hooper Island Straight lighthouse or take a ride on a traditional Bay boat. Shop on Talbot Street for microbreweries, ice cream parlors, antique shops, boutiques and art galleries.
As one of the earliest English settlements, Cambridge is a delightfully walkable town with restaurants, museums and a rich history. To be within walking distance of nearly everything in town, park the boat at Cambridge Yacht Basin. If you’re interested in the oldest working crab processing factory in the world, visit J.M. Clayton Company Seafood. For a quiet stay, visit Cambridge House Bed and Breakfast, or visit Hyatt Regency Chesapeake Bay Resort, Spa and Marina for a stand-alone, all-encompassing experience. The nearby Blackwater National Wildlife Refuge, a wildlife sanctuary, provides guided paddle tours where you’re sure to see bald eagles and migrating waterfowl. Learn about the life of the heroine who guided scores of enslaved people to freedom on the Underground Railroad at the Harriet Tubman Museum. The nationally renowned RAR Brewing originated here, while Blue Ruin specializes in delightful cocktails. Try the Portside Seafood Restaurant for the best in fresh seafood.
The tiny island of Solomons Island hosts boats of every kind, restaurants full of fresh seafood, a boardwalk, and a downtown of shops and hotels. For the kids, visit the Calvert Marine Museum to see river otters, skates and rays, touch a giant fossilized shark’s tooth or take a ride on a traditional Chesapeake Bay buyboat. The island is both charming and entirely walkable, making the multiple marinas, B&Bs, marine museums, boardwalks and restaurants easily accessible. For the inner scientist, be sure to visit the Chesapeake Biological Lab, featuring seminars and tours. With plenty of options for food, be sure to check out highlights such as The CD Cafe, and Charles Street Brasserie.
Although small, Onancock is well-loved. Surrounding by marshes and populated by restaurants and shops, it is popularly explored by foot and bikes. Due to the easy boat access, Onancock Wharf and Marina is an option for overnight lodging, as is the Charlotte Hotel, which features two dining rooms, a lovely bar and eight guest rooms. Onancock also provides an abundance of B&Bs like the Inn at Onancock with tastefully decorated with international themes. When exploring by water, launch your personal paddle-able boat or rent one from Burnham Guides, or climb aboard a cruise with Holly Cove Charters or Onancock Sailing Adventures. Visit Market Street for an abundance of galleries, stroll through the weekend market, take in a flick at the historic Roseland movie theater, or tour the historic Ker Place. Do not miss the Corner Bakery, a cult favorite among locals and tourists alike. Bizzotto’s Gallery Cafe, Mallards at the Wharf, the Blarney Stone Pub and 3 Knots Taphouse are all local staples for dining and companionship.
Cape Charles is a charming village filled with shops, restaurants and one of the best Bay beaches. The Cape Charles Yacht Center offers comprehensive marine services, while the Oyster Farm Marina at Kings Creek offers fresh seafood in a waterfront setting. Hotel Cape Charles and Bay Haven Inn provide charm and great breakfasts. Southeast Expeditions offers unique paddle tours, or go fishing on one of Cape Charles’s fleet of charter boats. The town boasts a half-mile-long white sand beach, complete with a fishing pier. In addition to the beach, Cape Charles is home to shops such as Table and Tonic, Lemon Tree Gallery and Peach Street Books. The quaint Central Park, Cape Charles Museum and Cape Charles Library provide lovely views, unique architecture and deep history. Cape Charles Distillery and Kelly’s Gingernut Pub are both friendly spots for a refreshing quaff. The Shanty, and Deadrise Italian Kitchen are the locals’ favorite restaurants.
Although 75,000 people make the trek to the Urbanna Oyster Festival every October, there is much more to this charming town than just oysters fresh-shucked on the half shell, roasted, fried or stewed. If you’re looking for a place for the boat to stay, check out Bridge Marinas. If you’re looking for a place to stay check into The Chesapeake Inn, or look to the Bethpage Camp-Resort for cottages and even a waterpark. Walk around town to take in its rural charm, or launch a paddle from multiple launches. Something Different specializes in “Fine Neanderthal Cuisine,” Where the Sidewalk Ends provides delicious baked goods, and Marshall’s Drug Store’s lunch counter offers some of the best milkshakes around. And of course, if you find yourself in Urbanna in October, check out the world-famous Oyster Festival.
With possibly more boats than people, Deltaville proudly claims itself to be the boating capital of the Chesapeake Bay. Although there is no downtown in Downtown Deltaville (a hint to its scarce population), the town features some of the best sailing, paddling, fishing and cruising waters on the Chesapeake. The town huddles along the shoreline, with marinas that provide bicycles to make getting around without a car easier. The Cross Rip Campground offers waterfront cabins with character as well as campsites for tents and RVs. For a bite to eat, visit J&W Seafood and Gourmet Market for the freshest seafood around.
In addition to its history, Yorktown is packed with activities, from lively farmers markets to a Riverwalk with a summer concert series. In a small walkable area, Yorktown is teeming with restaurants and shops, museums and a great beach. Riverwalk Landing Piers is the town’s marina, but Wormley Creek Marina and York River Yacht Haven also offer hospitable options to boaters. For lodging, Yorktown Beach Hotel offers not only a fantastic location, but also a pool. The stately Hornsby House has been accommodating guests for three generations and has mastered their formal breakfast. Riverwalk landing offers not only slips for smaller boats, but options to launch your own paddle-able boat, or rent from Patriot Tours and Provisions. Williamsburg Charter Sails has three-hour sails for up to six people, or you can simply relax on one of the many public beaches. Among the numerous historical sites and touring options, visit shops for one-of-a-kind crafts, unique jewelry, rare books, or artwork. Yorktown Pub, Water Street Grille, and Carrot Tree Kitchens are all go-tos for fresh and local drinks, baked goods, seafood and pizza.
Leading right to the city’s doorstep, Hampton offers one of the friendliest yacht clubs around, an air-and-space museum and a historic town center. Bluewater Yachting Center has all the amenities needed plus more, in addition to the Hampton Yacht Club and Customs House Marina. The Landing at Hampton Marina is conveniently located for overnight docking, while the Magnolia House Inn offers B&B accommodations with an onsite wedding chapel. For launching personal kayaks or SUPs, look to Mill Point Park or River Street Park Canoe and Kayak launch. The sleek new tour boat, the Hampton Queen offers two-hour narrated cruises. Jet ski rentals are available at Great White Water Sports, Buckroe Beach and Park has a swimming beach, and Paradise Ocean Club offers resort-style accommodations. For other activities, the Virginia Air & Space Museum is a must, or visit the numerous other museums for a taste of history. There are plenty of fun bars and pubs, but Marker 20 offers live bands on the piers. The Deadrise at Old Point Comfort Marina and Surf Rider are both Virginia seafood staples while Goody’s Deli and Pub, Venture Kitchen and Bar, Brown Chicken Brown Cow, and The Grey Goose are all great options for great eats.
Among the historic buildings, churches and homes, Portsmouth has a vibrant nightlife with first-rate entertainment venues, highly regarded restaurants, and weekends highlighting crafts, music and antiques. For those arriving by boat, Portsmouth is bookended by two marinas, Tidewater Yacht Marina and Ocean Marine. Everything in between is within an easy stroll, providing lovely B&Bs as well as the elegant Renaissance Portsmouth-Norfolk Hotel. When looking for activities, take a walk through Olde Towne to breath in the history, or shop at Skipjack Nautical Wares and Gallery or the Little Shoppes on High. You can board the Lightship Portsmouth Museum for a glimpse of local maritime history, The Atlantic Union Bank & Trust Pavilion hosts top-name performers, and the Portsmouth Art and Cultural Center offers a multitude of art offerings. Try the Yoolks on Us for real Southern grits, or for a taste of international fare, don’t miss Cafe Europa, Still Worldly Eclectic Tapas, and The Bier Garden.
Isabel Littman is a recent graduate of Key School in Annapolis and a former CBM intern. She will be attending the George Washington University this fall, majoring in journalism.