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

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

Singing & Sailing into the Sunset

Sailing into the Sunset with local music aboard the Woodwind

Woke up to the sound of rain. So much rain, that no one signed up for the first sail today.  By the second sail, 3:00-5:00, we had 2 lovely people sign up. They had a private cruise (for $72)!  We had perfect wind and made it under the Bay Bridge and back. Maureen and Jim … Read more

Don’t Waste the Wind

Playing with Woodwind

Today, the breeze was blasting out of the SSW, just under 20kts at times!  The conditions were perfect: warm sun, cool breeze, and flat water.  Still, we had very few people aboard.  If you are reading this, I advise you to take the kids out of school, call in sick to work, and leave the … Read more

More Wind Please….

Schooner Woodwind on the Bay

I think almost every time you mention the word Regatta the winds head the other way. At least that is what I am blaming the lack of wind on. Thisweekend is the Annapolis Race Week Regatta and I feel for all those people out there drifting around with out any wind. Hope fully today will … 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

Circumnavigating a Submarine

Sailing around the submarine off of Annapolis

The first day of Labor Day Weekend has begun. We had about 25 people on our early sail and we had about 10-14 knots of breeze. Within a half hour of the sail, we spot a submarine in the distance. We just had to check it out.  I decided to circumnavigate the sub, while staying … Read more

Breeze + Music= Great

"The Roadside Show" performs on the Schooner Woodwind

We had some great breezes today. It’s funny how “great breeze” might be defined among the captains and crew on the Woodwinds. To us, the crew of the Woodwind II, for today… we had great breezes. Why? The forecast was for no breeze. While we were getting the boat ready to sail, we had no … Read more

Fish, Sail, Fish

Sailing the Schooner Woodwind into the Chesapeake

The day started by a warm greeting on the dock by Steve. He admired the Woodwind for many years and was excited to finally make today the day he was going to sail on her.  He was out fishing earlier on his boat and he said it was blowing around 18 knots. He shared that … Read more

Close Encounters of the Crew Kind…

Fran and Joe on Schooner Woodwind

So there I was on a beautiful Tuesday morning raising the sails when all of the sudden I was inundated with crew from all directions and in all types of water craft. Capt. Jen on the paddle board, Whitney on the laser, Sam in the blue kayak and Jocyln in the red kayak. What a … Read more

Schooner Woodwind
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