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Cruising the Chesapeake Bay: Baltimore by Boat

By Zuzana Prochazka

Steeped in history, Baltimore is a destination like few others and a must-see while cruising on America’s largest estuary, the Chesapeake Bay. Halfway between the northernmost town of Charlestown and historic Annapolis on Maryland’s western shore, Baltimore is an unlikely charter destination for the uninitiated. Even the city’s recently unveiled tagline – A Great Place to Grow – does little to describe what a fun town it is to visit by boat. This is not a place to crab in a remote cove or bicycle around quaint villages like other destinations along the 200 mile stretch of the Chesapeake, but it is a city that is welcoming to boaters and so packed with things to do that a week will hardly scratch the surface.

national aquarium in baltimore

Baltimore City is jam-packed with attractions like the National Aquarium (with triangular roof).

Getting There

Although there is no shortage of local tourist boats to board for an afternoon of sailing, the best way to get the full effect of “arriving” in Baltimore by water is to charter out of Annapolis, only 30 miles to the south. The Moorings and Annapolis Bay Charters offer a great selection of boats, both power and sail. Fifteen miles up from the main bay, the Patapsco River dead-ends in Baltimore’s Inner Harbor, its landscape dominated by the Domino Sugar sign, a marker that you’ll find helpful no matter where you go on the historic waterfront.

As you sail under the Francis Scott Key Bridge, to starboard you’ll notice a red, white and blue buoy that commemorates the spot from where Key watched the Battle of Baltimore in 1814. Taken prisoner aboard a barge, Key wrote the lyrics to the national anthem here and you’d think the buoy would be large, but in fact, it’s pretty unassuming and set out only in spring and summer. The buoy is surprisingly far, over three miles, from Fort McHenry—which withstood 25 hours of British bombardment the night of Key’s composition. If Key saw the flag raised over the fort the next morning to signal it had survived, he had excellent vision and probably the help of a spyglass.

Winding up the harbor you’ll notice dozens of marinas, all of which welcome transients. The inner-most basin also offers a small anchorage with a mud bottom and city docks where you can tie up (and lock up) your dinghy. With the hook set in this very calm water, Baltimore’s city lights make a breathtaking urban backdrop for an evening of cockpit cocktails.

There is no shortage of marinas in the inner harbor or on the approach through the Canton and Fell’s Point neighborhoods. These are full service facilities that offer floating docks, water, power, wifi, pump-out, showers and laundry. Baltimore Inner Harbor Marine Center and a few others also sell fuel.

Going Ashore

Once ashore, strap on your walking shoes and explore the 7.5 mile waterfront promenade and all its attractions. Visit the National Aquarium with interactive dolphin shows or take in the view from the top of the I.M. Pei-designed World Trade Center. Walk over to the Fell’s Point district with its eighteenth century homes, cobblestone streets, charming pubs and outdoor cafes. This was the original deep water harbor in Baltimore and the place where the famous Baltimore clippers were built. Two odd facts about Fell’s Point: it was the second busiest port of entry for immigrants after Ellis Island, and for reasons unexplained, it was where the movie Sleepless in Seattle was filmed.

fells point in baltimore

Distinctive neighborhoods like Fells Point set Baltimore apart from other east coast cities.

The city of Baltimore, with its clusters of ethnic neighborhoods, is a living, breathing history lesson that is amazing to explore. Take a trolley out to Fort McHenry National Monument and Historic Shrine or visit the Star Spangled Banner House where Mary Pickersgill sewed the 15-stripe, 15-star flag that flew over the fort and inspired Key to put pen to paper. You can’t really miss the Pickersgill house; it has an enormous flag covering most of the wall outside. A tour of the house will make you wonder how she sewed a 30’x 42’ flag in the handful of tiny rooms.

No boater will be able to resist touring the Historic Ships of Baltimore, a museum of sorts made up of four historic vessels and a relocated lighthouse. Tour the US sloop-of-war Constellation, launched in 1854, and lightship #116, Chesapeake, that served as a mobile lighthouse from 1930 to 1965. Also included is the USCG cutter Taney which survived the attack on Pearl Harbor, and the USS Torsk, a submarine that participated in the 1962 Cuban Blockade and had 10,600 career dives. Part of the package also includes a self-guided tour of a screw-pile lighthouse that served to mark the Seven Foot Knoll shoal on the Chesapeake Bay, for 133 years.

It’ll easily take two days to get through just this part of the city’s attractions, but you can break up the walking by stopping for crabcakes at Phillip’s Seafood or one of the many other restaurants located in the historic building known as the Power Plant. Throughout the waterfront area and within a 10-minute walk, there are so many restaurants of all kinds and all price levels that thoughts of cooking aboard are likely to go right out the window.


Provisioning opportunities are all around and include a Whole Foods near Little Italy and the Lexington Market, first opened in 1782, which houses dozens of vendors selling everything from baked goods to seafood. This is also the home of the Preakness Crab Derby in April, where crabs are raced with the encouragement of spray bottles. The winnings go to charity.

chessie boats

For an unusual boating experience on Baltimore's inner harbor, "charter" a Chessie paddle boat for an hour or two.

For a spell on the water, you can board one of the dozen local operations that will take you on a harbor tour aboard a pirate ship or a historic clipper. Or rent a “Chessie” from Inner Harbor Paddle Boats and paddle out to take pictures of your boat anchored in the harbor. You can also daysail your own charter boat; during the month of October you can join Parade of Sails, a procession of tall ships and schooners that come from all over the eastern seaboard to participate.

There are over 80 museums, galleries, historic sites and attractions in the immediate area and you could spend a month in Baltimore and not get to them all. Baltimore is going out of its way to be tourist-friendly and is also accessible with a water taxi system (hail them on VHF Channel 71) and a metro. The city also has one of the best organized visitor centers I’ve ever had the pleasure to peruse. It houses maps and models and is staffed by friendly and informed people willing to plan your itinerary and book your excursions free of charge. And speaking of free of charge, the Charm City Circulator is a fleet of 21 free shuttle buses that travel four color-coded routes in the local area, making it easy to get to just about any of the attractions from Oriole Park at Camden Yards to the Korean War Memorial out by Canton.

Baltimore slipped into decline in the 1970s and in many ways got a bad rap. Now thanks to urban renewal projects, this vital town, which is the twenty-fourth largest city in the US, is now vibrant and full of great eateries, high-end waterfront condos, and tons of attractions. It might not be the first place you think of when someone says bareboat charter on the Chesapeake, but it should definitely be on the list. Urban cruising is a unique treat, and Baltimore is a charming place to do it.

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