Visiting Baltimore by Sailboat

See the Chesapeake Bay: Sailing Into Baltimore

If you have yet to visit Baltimore by boat, you’re missing out. I honestly can’t think of another East Coast city that celebrates and shares its waterfront more delightfully than Baltimore. I know that’s a bold statement, yet having sailed from Maine to Florida, covering 3800 nautical miles and visiting more than 100 waterfront towns and cities, I stand (at the helm) behind this statement. We were also five-month liveaboards in Baltimore and enjoyed first-hand experience with waterfront living in Charm City.

sailing into baltimore
The author motors her cruising sailboat into Baltimore through "the Gap" in the Key Bridge.

Deciding To Sail to Baltimore
I love to sail to Baltimore, yet I know several cruisers who consider it too much of a detour from their annual pilgrimages to points north or south. Other Chesapeake sailors consider Charm City just a bit daunting due to limited areas for anchoring and the absence of mooring balls. Should you decide to spend a few days or more in Baltimore, and I hope you will, there are countless activities to do and many convenient transit options to make your stay incredibly enjoyable. 

Take a Slip or Anchor?
Although we typically anchor in other towns, we usually take a slip in Baltimore at marinas that offer transient dockage. Two months ago for the Fourth of July festivities, we docked at the recently renovated Oasis Lighthouse Point Marina in Canton. We were quite impressed by their new management and amenities, including keyless gated access and in-slip pump-out connections. And wow, the unobstructed views of the fireworks from their docks were priceless!

For those who prefer anchoring, there is room for several boats between Lighthouse Point and Anchorage marinas, and some space a bit farther west closer to Captain James Restaurant. Across from the Canton Safeway, there is a small gazebo and pier where dinghies can be tied for shore access or provisioning. 

We enjoyed returning to these familiar surroundings while also noting many changes since we were liveaboards at this location in 2016. It’s hard to imagine that even more bars and restaurants have opened nearby, but they have, along with increased shopping options in Brewers Hill within a half-mile walk. Sailors don’t have to leave Canton to have all their needs met, including finding supplies at West Marine.

Boaters who prefer taking a slip closer to the pulse of the city can find several marinas stretching from cobblestoned Fells Point towards bustling Harbor East, turning the corner southward to historic Federal Hill. At any point, transient slip holders can join city residents in walking or running the scenic promenade that spans five miles of Baltimore’s waterfront, from Canton’s Waterfront Park to the Rusty Scupper at the foot of Federal Hill. Along the way, you’ll pass many restaurants, shops, and nautical landmarks, including the Seven Foot Knoll Lighthouse and the USS Constellation. 

fireworks baltimore
Fireworks from an anchorage in Baltimore on the Patapsco River off the Chesapeake Bay.

So Much To See and Do
I grew up outside of Baltimore before becoming an 18-year city resident, so I am quite biased when it comes to promoting the endless attractions in Charm City. Who can argue with seeing the Orioles or Ravens play just a few blocks from the Inner Harbor, visiting the National Aquarium, or catching a concert at Pier 6 along the waterfront?

When my husband and I were liveaboards, Charleston friends visited on their trawler after they had spent a month in Washington, DC. I was a bit concerned at first that I had oversold my hometown, but they had a blast immersing themselves in Baltimore’s history, novelties, and breweries. Even after a month, Mark and Cathy didn’t exhaust all the possibilities that were within a short walk, bus, or water taxi ride from Canton, including Fort McHenry, the Baltimore Museum of Industry, the B&O Museum, and the American Visionary Arts Museum. Their pub crawls from the Natty Boh sign to Fells Point were legendary. I’m just sorry they left before Sagamore Distillery opened in Port Covington. They have to come back!

Sailing Community in Baltimore
There is a very loyal sailing community in Baltimore. I should know because 16 years ago I met my husband on a blind date at the Downtown Sailing Center (DSC). DSC’s fleet of keelboats and cruisers enjoys a 99-year lease of docks scenically located between the Museum of Industry and Domino Sugars. 

The DSC is a not-for-profit community sailing center offering affordable instruction and programming for all levels of sailors, including beginners. On any day in the harbor or near Fort McHenry, you can see DSC keelboats gracing the waters. And if you happen to be in town on Thursday nights, be on the lookout for DSC competitive racers. When I was a member, I enjoyed their more relaxed Friday night “fun races.”


Francis Scott Key buoy that marks where the words of our national anthem were penned in Baltimore.

The Big Gap
It was a bittersweet journey when we sailed to Baltimore in July. While we knew it would be the first time we would sail under what was left of the Key Bridge since the cargo ship Dali’s fatal impact on March 26, it was impossible to anticipate the gap in our hearts and on the horizon until we drew near. The last time we sailed under the Key Bridge was last year on June 9 when we began our summer journey to Maine. Little did we know then that the bridge would cease to exist less than 10 months later.

Despite growing up just outside the Beltway and learning to drive shortly before the Key Bridge was completed in 1977, I had sailed under that bridge more than I had driven over it. As we approached “the big gap,” minding buoys designating Sollers Point Channel for recreational boats, we almost kept pace with a cargo ship on our port side. As tug boats escorted it to a nearby terminal, I couldn’t help but think about the sequence of events during those fateful hours in late March, and the six lives that were lost. 

It was a sobering passage through the gap, yet it was also heartening to see activity returning to the port, with several ships being offloaded and loaded as we sailed past. I was filled with hope and anticipation for the next chapter in Baltimore’s history as this resilient city plans the next gateway to its inviting harbor and vibrant neighborhoods.

Special Buoy
As we departed Baltimore the day after the fireworks red glare, we decided to circle the Francis Scott Key buoy that marks where the words of our national anthem were penned. For the first time in my memory, we had to wait our turn as we weren’t the only ones who felt compelled to pay tribute to this symbol of freedom. We were third in line and quite happy to patiently wait to offer a nod to Baltimore’s rich history and its hopeful future. We will return, and often.

~By Captain Cheryl Duvall

Find more great Chesapeake destinations here.