The Lady Maryland cruises on the Magothy River. Owned by the Living Classroom Foundation, she takes student groups aboard for a bit of education on the water.
Don’t know your starboard from your tack, your rudder from your keel? I’ve been sailing since I was 10 and I still don’t know all the lingo. (Sorry, Dad. I know you’ve taught me.)
It really doesn’t matter whether you can come about or jibe to enjoy an afternoon on the water. What matters is getting out there.
Time for Seabrina to get back to work as sailing season gets underway.
All those wonderful things they say about sailing really do make a day on a sailboat memorable: the sun in your eyes, the wind at your back, the splash of the water, the unexpected visitors — whether it’s the tiny spider attempting to spin a web on your mast, the monarch butterfly taking a breather on the boom, or the fish that jumps out of the water right beside your boat.
Plenty of sailors are ready to take on a few new crew members. Sometimes they’ll even let you take the helm. Or at least a drink!
Sailing is family time for my crowd. FlipFlop, my brother’s boat, was so big you could bring a crowd.
My boat of choice is the miniscule Seabrina. At 19 feet she can’t take too many extra passengers. So sometimes, I have to get on a bigger boat.
Most people want a more comfortable ride anyway. Something bigger. Something with enough sail to get them somewhere. Something with beverage service. Or a captain with good stories. Or at least room to walk around.
The Baltimore-Annapolis area has plenty of options.
The Skipjack Rebecca T. Ruark
Here are a couple of sailboats most worthy of a day away.
Rebecca T. Ruark —
Here’s an authentic Chesapeake Bay experience. Docked at Tilghman Island, Captain Wade Murphy sails the oldest working sailboat in the country. He’ll tell you a tale or two about the bay, oyster dredging and crabbing.
The Schooner Woodwind I and II during Wednesday night races.
Schooner Woodwind —
A ride on the Woodwind takes you out into the Chesapeake Bay, usually towards the twin spans of the Chesapeake Bay Bridge. It’s a good way to get out on the water, see the U.S. Naval Academy and the colonial city from the water. Come on Wednesday night and sail among the sailors out for blood in the Wednesday night sailing races. The Woodwind I and II get in on the action, too.
The Pride of Baltimore — the view from the bowsprit.
The Pride of Baltimore —
Baltimore’s “Star Spangled Ambassador” is sailing to the Great Lakes for the summer, so sailing fans in the mid-West have an opportunity to climb aboard. The graceful schooner hearkens back to Baltimore’s shipbuilding and privateering days. She’s pretty big and just plain pretty. Always fun to sail on the Pride.
A yellow beauty, the Sultana calls Chestertown her home port.
Sultana —
If your travels take you to Chestertown, you might like a cruise on the Sultana. The reproduction schooner is a replica of a Boston-building ship used by the British Navy.
The Kalmar Nyckel —
The original was a Dutch ship which brought the
The Kalmar Nyckel spends most of its summer in Lewes, Delaware.
original settlers to the land now known as Delaware. A yellow pinnace with lots of sails and scrollwork, she’s a beauty, sailing out of Lewes, Delaware, as well as Solomons in southern Maryland, Cape Charles, Virginia, and Massachusetts. I always thought she looked like a dandy pirate ship and — guess what? — she has pirate cruises, too.
The Selina II sets sail from a dock in St. Michaels.
Selina II —
For something a little closer to the water, I’d go with the 41-foot catboat Selina II, which sails out of St. Michaels. She’s gaff-rigged with one enormous sail and plenty of gleaming wood.
The Lady Patty sails past an old lighthouse.
The Lady Patty —
which sails out of Knapps Narrows at Tilghman Island is another smaller sailing choice. A 45-foot ketch, this classic wooden boat won the St. Petersburg to Havana Race in 1951.
© Text and photos Mary K. Tilghman (Updated June 2016)
Photos of Pride of Baltimore, Schooner Woodwind, Lady Patty, Selina II, Kalmar Nyckel, Sultana and Rebecca T. Ruark courtesy of their organizations. Schooner Woodwind photo by Rich Trevelyan. Lady Patty photo by Jim Tadder.
A Day Away Travel 
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