2024 Sailing Season is coming! See you April 13, 2024!

Hannah and the Roadside Show

Abraham and Hannah encourage Ann at the helm

The title is somewhat misleading.  During our 1:30 cruise we had Hannah and her guests.  In the evening we had the duo, Roadside Show sing for our guests. Hannah worked for us several years ago and just recently got married to Abraham.  She and her extended family joined us sailing this Wednesday.  In the photo is … Read more

Beer Tasting and traditional craft

Our guests and the Pride of Baltimore II

What could be better than sailing on Schooner Woodwind on a beautiful evening?  The answer for some would be, great sailing with a delicious beer from Flying Dog Brewery.  That’s why we had Ben, one of the brew-masters from Flying Dog join us. That’s Ben in the foreground with the gray hat.  Behind him to … Read more

Woodwind Greets the Pride of Baltimore II

Uploaded ToWoodwind Greets the Pride of Baltimore II

This Friday, as Woodwind sailed back from her evening cruise,the crew spotted The Pride of Baltimore II.  We retrieved our 10 gauge signal cannon and bore down on the Pride.  Crew, Andy Barton waited until the perfect moment and fired.         Firing a cannon (with blanks) is a traditional way to welcome ships into … Read more

Chilly Saturday, Great Sailing

Racing across the bay

  May 4th was a chilly day with a brisk wind.  We set sail and headed for the Bay Bridge.  Darren and Gigi are enjoying the sail as we fly along at 10 knots with just main and jib.  I have a sweater and sailing jacket on for warmth. Darren deserves to rest, because he … Read more

Sandbagger? “What are you talking about?”

Skipjack on the Bay

We had an unusual combination of circumstances to make today’s cruise special and hopefully this will result in a unique blog.  The most important part of the blog is that one of our guests, Luc Lapointe, is an excellent photographer and was kind enough to share his talent with us.  Thank you Luc. I have a … Read more

FAST Sailing, Some science, Lots of excitement

Woodwind sailing cruises Marriott Waterfront Hotel, Chesapeake

The wind was blowing 18 to 25 knots from the South.  This is a windy day with a little bit of chop to produce spray enough to occasionally douse the guests forward.  With the sun and warm temperatures, the spray is refreshing.  We are flying through the water and at one point hit 11 plus … Read more

Smiles, LARGE Freighter, Sunset

Little girl sailing the schooner with a butterfly shirt and a big smile

Was today perfect sailing conditions?  Taneka thought so. She is in first grade and her smile is the best answer to the question.  We had 15+ knots from the South with sunny skies. We have just passed under the Bay Bridge, thinking, “10 knots is really fast.”  Crew member Jocelyn clears her throat and says, … Read more

Lower the Main Sail

Schooner coming into port at dusk

The wind was light, but pleasant.  We have sailed into the harbor.  Reluctantly, I turn on the engine and head Woodwind into the dying breeze and order the main lowered.  Andy, our crew member is able to get two young sailors to help lower the sail by pulling in our reef lines.  I call to … Read more

What Do You Do If?

What do you do if there is no wind?  It was a beautiful cool evening, so we motored up the Severn River.  We are very fortunate to have such a beautiful area to show off.  We had many of the children on board take the helm.  As you can see, for young Caroline, it was … Read more

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