Archive | Captain’s Blog

Sunset over Annapolis,Md. from Schooner Woodwind on 7.29.12

Worthy of a Picture

We had great sailing conditions all day. The weather forecasting a chance of rain and light winds. We had no rain and the winds were in the 5 to 8 knot range most of the day. With the temperature topped out at 84 degrees it was a delightful day of sailing. And the people agreed. […]

Great photo as Woodwind II passes us at sunset in Annapolis

Best Sunsets lately!

Our first sail was a private charter for a pretty full boat. The partners of the company were taking out their summer interns to say thank you. The bottles of bubbly were a favorite amongst the crowd. We had some very interested folks who loved sailing the boat and talking with me about navigation. We […]

Schooner Woodwind at the Races

Frequent sailor Wednesday

Everyone that has sailed with us knows that at the  end of every sail we do we pass out frequent sailor cards to everyone. This is to encourage you to come sailing with us again and again. After sailing 5 trips with us you get your 6th trip free and you also get a free […]

Wednesday Night Racing on the Schooner Woodwind


Today we had a 4 1/2 hour team-building cruise on the Bay. A company chartered us out to have their team have fun, but also work together. It was a nice small group of only 12 people, so after lunch, we started the training. It was very interesting to see how everyone got along and […]

Thomas Point Light

Thomas Point Light

The winds were fantastic all day. Thanks for whoever prayed to the wind gods for us. We were able to sail down to the Thomas Point Light 3 out of 4 sails today. We had tons of great people out on the boat. A couple of mermaids joined us from Baltimore and we talked them […]

Monday, Monday

Everybody has their expectations of what Monday should be like. I am like everyone else. I was expecting a light wind, hot and maybe rainy day. Boy was I suprised. We had 4 great sails today. The wind was a little light but we never got any rain and the breeze was much better offshore […]

Wine in the Wind on Schooner Woodwind in Annapolis

Wine in the Wind

What a terrific day! I love the wine tastings we do on the Schooner Woodwind! French Wines were the theme today, each “Wine in the Wind” has a different theme. Franck Agostino was the host today. And he knows wine. His job is the coolest job, I might add. He is from France and he […]

Fun loving group from Cincinnati aboard the Schooner Woodwind II

Smiling in the Rain

It was a rainy Saturday.  Everyone is calling, “are you still going sailing, even in the rain”? Yes, we sail rain or shine. Ponchos were handed out to everyone and the rustle of poncho plastic made each sail unique. We had wind, a nice breeze from the NE that had us doing about 8-9 knots. […]

Woody, the grasshopper, goes for a ride on Schooner Woodwind

Friends and Mascots

We always get the most wonderful people that sail on the Woodwinds! On our 11:00 sail, we only had 7 guests aboard. But they felt like friends immediately.  Dave was celebrating his birthday with his grandparents (almost 21st birthday) and he had a blast learning all about sailing. He was hooked into the love and […]

Thank you Mother Nature

Today was a very interesting day on the Woodwind. We had a team building for the first 2 cruises and then 2 public sails afterwards. One of those public cruises was the Wednesday Night Race. Thank you Mother Nature for 15 knots of wind from the SW! We had a good teambuilding with a company […]

© Copyright 2017. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

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