2024 Sailing Season is coming! See you April 13, 2024!
Captain Jennifer 
We started the sail with virtually no wind, so I decided to motor to Thomas Point Lighthouse. As we get close, the wind picked up and were able to sail back to Annapolis. We anchored with great visibility of the fireworks and of the city skyline. All I kept thinking of was how lucky I … Read more
It was a scorcher… on land. Out on the water we had a nice breeze for 3 of the 4 sails. The first sail was the battle of the land breeze with the sea breeze. We had good breeze, until we sailed in the convergence zone where there was none. This is always fascinating to … Read more
We had a busy day with private charters. We had a company do a shmooze cruise with clients that they wanted to say thanks for all the business that they give them. I like the word shmooze cruise. They chartered the boat for 4 1/2 hours, and we got to Thomas Point Light, under the … Read more
What a terrific day we had on the water today!! The first sail we had a girl scout cruise along with some other public guests. They were treated to some fantastic sailing. We started with all 4 sails, and had to lower the fisherman before we tacked as we made it under the Bay Bridge. … Read more
Tonight, we sailed with one of my favorite groups of the season… J-Word Sailing School. All season, we sail around each other telling our guests about their sailing school and what maneuver they are teaching their students at that moment. It may be a man overboard drill, how to hove-to, or just how to sail … Read more
A beautiful Saturday filled with wind seemed like a fairy tale. But that is what we had for the 11:00 sail! We sailed straight across the Chesapeake Bay. Cool breezes with low humidity was a wonderful way to start the day! The low humidity was with us all day. The breezes slowed down as the … Read more
It was a strange day on the water. All sails except the first sail had virtually no breeze for a part of the cruise. And then all within the same cruise, the wind picked up and we were going 7.5 knots and the boat is healed over. Most of this was due to small clouds … Read more
The heat is on!! Wow, what a hot day yesterday… but we had a nice breeze on the boat. Our first cruise of the day was a Girl Scout Troop from VA. They were juniors learning our Sailing & Navigation program. After the cruise they were going to do the Geocaching Adventure Trail that we … Read more
A very light air day we had today. We were able to sail on all of our sails even though we didn’t venture very far into the Chesapeake Bay. But the flat water did help for viewing of the wildlife on the Chesapeake. We saw our first baby osprey head above the Red #4 Day … Read more
On June 9, we had four great sails with great people and very flukey winds. On our 4:00 sail, we were sailing with a Sea Breeze in the Chesapeake Bay, meanwhile the other Woodwind, with Captain Ken (Woodwind II), was sailing in a breeze blowing down the Severn River. Truly amazing wind conditions out there. … Read more