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

Local Everything aboard the Woodwind II

After the sunset, the skies above the Chesapeake Bay Bridge turned into Cotton Candy.

I wish I had my better camera aboard! So, if you were on this cruise, seeing this post, please send me some pics. Many of my pics came out blurry. Local Everything…. what does that mean? To me, it means getting as much things locally sourced as you can and presenting it all on a … Read more

All Smiles on Woodwind II

Young Millie sailing Woodwind II while "racing" Woodwind back into the harbor.

Temperatures were in the low 80s, winds were blowing around 15 knots all day, and interesting clouds kept the sun from shining directly on us. We had four really fun sails, and we were able to sail to the Bay Bridge and back on 2 cruises. The other 2 sails we sailed completely across the … Read more

“It’s so much Nicer on the Bay”

Everyone was amazed what a nice breeze could feel like on a hot summer day on the Chesapeake Bay. We had a great private, corporate event on the first cruise. They loved the relaxing sail, and were anticipating the amazing crabs at Cantler’s Crab House. The second cruise was terrific, especially when four year old … Read more

Heat Wave on the Woodwind

Jack Sherwood and Captain Jen at the helm

It has been hot these past days! There was a little wind today which made us have a nice day. Our first cruise was a corporate team event where High’s Convenience Stores chartered both Woodwinds for a Crew Match Race. We got our teams ready on the fisherman sail winches and our other stations. There … Read more

Breeze On

Storm clouds with the golden glow of sun on the other side of the storms.

As soon as we set sail, and sailed beyond Horn Point, we knew today was going to be full of breeze and fun.  We had half filled boats for most of the day because of the heat. But with heat, it brings on the breeze on the Bay. So the people who sailed with us … Read more

First Dates, Birthday and Alligators?

Donna & Scott Richardson sailing the schooner and smiling

Predictions for a breezy afternoon came true!  Great winds on all the sailing trips made for a terrific day of sailing on the Bay. On our first cruise, we scooted nicely under the Bay Bridge and back. As we headed to the bridge, one of the passengers, Donna, said to me. “It is so great … Read more

Happy Independence Day

Fireworks over Annapolis

Wind on July 4th?? With no threat of rain?? Delightful! We had 2 great sails to the bridge and back! And then we found a great spot to watch the fireworks, they were really great this year. And, in typical Annapolis fashion, there were 5 or 6 leftover fireworks from the finale that they shot … Read more

Perfect night on the Woodwind

Racing into Annapolis Harbor

  We had just one sail today on the Woodwind, the other boat had all four cruises, but we only had one. Tonight was a private event, I call it a shmooze cruise. Well the weather and breeze could not have been any better for saying thank you to your best customers. We put up … Read more

It’s Not Always about Going Fast and Racing…

Another beautiful sunset from the Woodwind.

We had a very light wind day today on the Woodwind. And we had a 4.5 hour private event for employees and their families of a nearby engineering firm. They brought a bunch of kids that were very inquisitive. We did our very best to keep them happy and into the sailing even though we … Read more

Monday Funday!

Beautiful sunset on USNA

We had such a nice, small cruise on the 11:00 sail on Monday. Our crew member Frank wanted to show the kids aboard how to navigate by using a chart. Hayden, was very intrigued by the entire process. Frank showed him how to triangulate a position using lines of position and how to use a … Read more

Schooner Woodwind
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