Archive | Captain’s Blog

Let's go sailing..rain or shine we have a good time

Rainy Day Tuesday……

The 100% chance of rain didn’t scare these guys off. They came prepared with their own ponchos. Mom’s birthday was going on no matter what the weather gods said and we went sailing. Mom and Dad had been out with us 10years prior to celebrate another birthday with us and decided to return and bring […]

Om plays a popular tune that might have been played as the ship "Peggy Stewart" burned to the waterline and then sank.

History, Violin, and Taking the Helm

Tom Gay has a perspective of Annapolis that is unusual.  He shares that perspective with our guests as we sail towards the Bay Bridge, explaining how Governor Preston Lane ran for re-election on the promise that the bridge would only cost “pennies a day”.  Everyone new what that meant: TAXES.  And they did not want […]

Thomas Point Lighthouse from the Woodwind

Lighthouse Cruise 2014

A beautiful day for a cruise to see lighthouses. As for the wind, it was light too. We tried to do as much sailing as we could, and managed to sail about 1/3 of the time. The other time was spent motoring (and making a nice breeze over the boat) as we headed to see […]

Sam's helper on the stay sail

Another great day on the Bay…….

The wind was almost non-existent today, but that did not stop us from having a great day. We started out the day with the sighting of one of the beautiful yachts that lives here in Annapolis part of the year. The S.S. Sophie. She steamed passed us as we were setting sail and heading out […]

Click the picture to watch the Woodwind Wave!

Wave! It’s your Birthday!

Our day started around noon on Woodwind II. We were planning on doing three sails that were all public, 2-hour cruises. The day started with Woodwind (with my Dad aboard) going into Back Creek for a tour of the local waterfront marinas and properties. This is what we sometimes do when there isn’t much wind […]

Erinn at the helm of the Schooner Woodwind

Monday and it still feels like the weekend……..

The boat was full most of the day and it felt like we were operating on a Saturday or Sunday. FUN…Lots of people and good sailing to boot. Erinn and her grandfather came out for a sail today and this was her training run. Erinn’s grandfather operates a couple of ships in the Caribbean and […]

Gorgeous sunset from the helm of Woodwind

Wind Dance- Its Only Weird if it doesn’t work!

Can you really ask Mother Nature to provide you with wind if you offer up a boat full of people doing the Wind Dance? Our first cruise we had a great family reunion of the Court Family.  Many of them sailed the boat and enjoyed the time at the helm- including the little ones. The […]

Evan at the helm of Schooner Woodwind

94 years young….

I hope when I am a retired sailor that I have the spunk and energy of Evan Bostdorf. Celebrating his 94th birthday he came out with us today with family and friends and won the hearts of all. It was a pleasure to have you aboard. Happy Birthday Evan!!! It was awesome day on the […]

Launching of Woodwind III

I know many of you have have been asking about the possibility of a third vessel.  Well, after much head scratching and fund raising efforts, we finally are announcing today that Woodwind III has been launched.  We will now share these photos of our new venture.  Sam was chosen as captain, Mike W as 1st […]

Sailing on the Woodwind

Is this the same schooner?

The first conversation of the day started with, “Is this the same schooner?….” We get this question a lot, followed by “as used in the Wedding Crasher’s Movie?” But this was a different question… “as the one that was here, maybe 17 years ago?” I answered them, “yes it was, did you sail with us […]

© Copyright 2018. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.