Cruising Stories

Cruising The Chesapeake Bay - From Baltimore to Cape Charles

Eight Chesapeake Ports of Call

Capt. Jeff

Cruising the Chesapeake Bay - From Baltimore to Cape Charles

A spectacular North American cruising ground was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. The Algonquian word Chesepiooc, meaning at a big river became the source of the name for the estuary now called the Chesapeake.

Starting Point


The attractions of the historic Inner Harbor seaport are within easy walking distance of several marinas. A must-do list includes the National Aquarium and the Maryland Science Center. Tour the USS Constellation, built in 1854, the last sail-only warship built for the U.S. Navy. The lightship Chesapeake offers a fascinating opportunity to discover life aboard a floating lighthouse.

In the Harbor East neighborhood you will find an array of high-end shopping and dining as well as provisioning at Whole Foods. Baltimore Marine Center offer four locations throughout the Inner Harbor and Hendersons Wharf is located in the historic Fells Point neighborhood. Tidewater Yacht Service, Baltimore's premier yacht service facility, is located just west of Ft. McHenry. Fuel can be found at BMC Inner Harbor or BMC Lighthouse Point.

Leg 1-Estimated Mileage: 30


A walking tour of historic Annapolis, which is arrayed like spokes in a wheel from the Maryland State House, will delight architectural aficionados. Examples of Federal, Italianate, Georgian, Queen Anne and Greek Revival styles from the colonial period through the early 1900s abound.Good provisioning near the marina is hard to find. The locals' favorite, Graul's Market, with excellent produce, meat and fish is a mile and a half away. However, the marina has rental car and taxi services available to help stock up at Trader Joe's, Whole Foods and Fresh Market. The Annapolis Yacht Basin has fuel and Annapolis Harbor Boat Yard is a full service maintenance yard that is conveniently located on Spa Creek near the historic district.

Leg 2-Estimated Mileage: 29


For boaters, the focus of this Eastern Shore town is the Chesapeake Bay Maritime Museum with exhibits, restored vessels and hands-on boatbuilding workshops. It is where James Michener did his primary research for his best selling novel, Chesapeake, 40 years ago. The picturesque streets of St. Michaels are perfect to stroll along while looking for lunch or dinner.Topping off provisions is easily done within walking distance of the marina at Olivins, a gourmet grocery, or Acme supermarket. Fuel is available at St. Michaels Marina. Higgin's Yacht Yard is the last full-service boatyard in existencein town.

Overnight Stop: Leg 3-Estimated Mileage: 40


Oxford's main attraction is the town itself. It is one of the oldest towns in Maryland, officially founded in 1683. The charming, tree-lined village is a quiet antidote to the hustle and bustle of city life.The Oxford Market, a convenience store, is the only spot in town to buy any essentials for provisioning. If you need fresh fish and seafood, watch for the watermen when they bring their catch in early in the day. The marina is also a full-service boat yard, with gas and diesel available. Hinckley Yacht Services also has a full-service yard in town. Both Brewer and Hinckley provide quality work and craftsmanship.

Overnight Stop: Leg 4-Estimated Mileage: 40


Located at the mouth of the Patuxent River, Solomons Island was famous for its wooden sloops, schooners and bugeyes, built for the island's fishing fleet. Today, visitors come to see the Calvert Marine Museum and the restored Drum Point screw pile lighthouse exhibit.Zahniser's Yachting Center is an institution on the Chesapeake for boat owners. Not only do they have a full-service boat yard and marina, they also boast a swimming pool with a bar and grill for transient boaters. The pool is a fine summer's treat after a day on the water. For additional provisioning, Zahniser's provides a car with a driver to the nearest grocery store. Gas and diesel can be taken on at nearby Solomons Yachting Center or Spring Love Marina.

Overnight Stop: Leg 5-Estimated Mileage: 42


Tangier Island is the home of working watermen who get up well before dawn to get their boats ready for crabbing and oystering. The island is most well known for its soft shell crab, for which it claims to be the world capital. With a total population of about 700, most who live there can trace their ancestry back to a handful of families. The small settlement is unique to the Chesapeake and wandering its lanes is the ideal way to pass the time after lunch or dinner at one of the two local restaurants. And, of course, order soft shell crab and crab cakes.Parks Marina is just across the harbor channel from the many crabbing shacks built on stilts along the shore. The marina is owned and operated by 85-year-old Milton Parks, and is a simple affair with fixed docks, pilings and a faded signboard. Milton gladly offers advice on how to dock in the strong current and, once your boat is tied up, he will spin many a story of the island's inhabitants and history. Daley & Sons is the only grocery store on the island. There are no repair or fueling services for recreational boaters on Tangier Island, but in a pinch a waterman may be able to provide some assistance.

Overnight Stop: Leg 6-Estimated Mileage: 35


While at the marina, it is well worth taking advantage of all Tides Inn has to offer. The resort was developed from a waterfront farm 70 years ago, and today its outstanding amenities make it a premier resort. Play a round of golf on the Golden Eagle Golf Course or try classic treatments at a Chesapeake Bay inspired spa. Just a 10-minute walk from the marina is the Steamboat Era Museum, paying homage to the steamboats that connected the waterfront communities on the bay from 1813 until 1937.The best option for provisioning is the Tri-Star Supermarket located about 5 miles from the marina. And both diesel and gasoline are available at the marina's fuel dock. Rappahannock Yachts is a family-owned full-service boatyard on Carters Creek, close to the marina.

Overnight Stop: Leg 7-Estimated Mileage: 41


Some cruisers who have visited this revived, historic railroad town on Virginia's Eastern Shore say it's one of the Mid-Atlantic's best-kept secrets. Life is easy in this inviting bayside town, with bikes and golf carts sufficing for transportation and menus heavy with local seafood. With most of its structures built between 1885 and 1920, Cape Charles has one of the largest concentrations of restored late-Victorian and turn-of-the-century buildings on the East Coast. Many of these beautiful structures are now transformed into bed and breakfasts, galleries and specialty boutiques.The Gull Hammock Gourmet Market and Drizzles are two high-quality groceries for additional provisioning. They are adjacent to the historic district and conveniently located on your way back from the beach to your boat. At Cape Charles Yacht Center, yachts have full access to nearby Bay Creek Resort, featuring a Beach Club pool as well as two signature golf courses designed by Jack Nicklaus and Arnold Palmer.

Capt. Jeff Werner has been in the yachting industry for over 25 years. In addition to working as a captain on private and charter yachts, both sail and power, he is a certified instructor for the USCG, US Sailing, RYA and the MCA. He is also the Diesel Doctor, helping to keep your yacht's fuel in optimal condition for peak performance. For more information, call 239-246-6810, or visit All Marinalife members receive a 10% discount on purchases of equipment, products and supplies from Diesel Doctor.

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