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

Charters,Charters and More Charters……

Women steering the schooner and doing a fist pump

And that is exactly what we did today on Woodwind II, Charters all day. But what fun. We got to go farther afield than we normally get to and saw some fun sights all day. We started the day with seeing the start of the SUP Chesapeake Challenge as they came by the entrance to … Read more

Let’s go Sailing……

Smilin Jack! At the wheel of the Schooner Woodwind

Jacks parents grew up sailing in Barnegut Bay and had a small boat named Smilin Jack. And their son is wearing one of their old hats they had made for the boat as he captains the Schooner Woodwind. How fitting!! Jack and his family joined us from Virginia today. It was a pleasure to have … Read more

Monday Sailing, and what great winds………..

Jason at the Wheel of the Schooner Woodwind

Monday was a great day for sailing. The  winds were in the teens all day. We were able to get under the bay bridge 2 out of 4 sails.Yeah. On our 1st sail Capt. Jason took the wheel and safely guided us through out the Chesapeake bay and Severn River. Good Job Jason!!! Always fun … Read more

History of Greenbury Point…..

Sunset over Greenbury Point

Every Monday is History Day on the Schooner Woodwind. This weeks subject  was on the history of Greenbury Point. Our speaker, Janet Williman, is  very engaging and takes the time to come around the boat and talk to everyone in small groups so all can hear. Thank you Janet for another educational trip. It is … Read more

Flying Dog’s Dead Rise Beer is on board…..!!!

Picture of Dead Rise Summer Ale

That’s right. The hardest beer to find in Maryland is on our boat. So come on out on every Tuesday in  the month of June and enjoy a free sample. Every Tuesday aboard the Woodwind is our beer tasting night. This month we are featuring the Flying Dog Brewery from Frederick,Md. The starting line-up is: … Read more

New Friends and Old Friends…….

Great day of sailing on the Schooner Woodwind II

We had some fun kids out on the boat today. Nia joined us along with her family all the way from Atlanta,Ga. She could not get enough helm time. Look at that smile. We had small groups all day so we were able to give her plenty of time behind the wheel. Braeden and his … Read more

Wine in the Wind…..Italian Style

Look at those smiles. Dee and Dave just got engaged on the schooner!

And what a great day it was for it!! The sun was out and the winds were blowing 10-15 knots all day. Yeeha hold onto your hats. We started our day with a trip full of girl scouts doing our Power of  Team program. They got to learn about the boat, trim the sails and … Read more

Can you Believe this weather……

If you would have told me that I would be sailing in this kind of weather in June in Annapolis , I would have thought you were joking. We had cool temps. and a nice breeze that just made it so enjoyable to be out on the water. On our 1st trip of the day … Read more

Rainy Day Friday….

We weren't the only ones out in the rain....

Friday was one of those days you wish you were in front of the fireplace snuggled up with a good book and some hot chocolate. But we decided we would go sailing instead with the few brave souls who ventured down to the docks today…. I pulled out the gore-tex gear and weathered the storms … Read more

Schooner Woodwind
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