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

Songs of the Chesapeake….

Deanna Dove aboard The Schooner Woodwind

This was our last Music Thursday of the season. But that did not stop us from enjoying 3 great sails today. Starting out it looked as if we weren’t going to have much wind, but as we came out of the harbor the wind picked up as we headed for the bay. The number of … Read more

Dogtoberfest….And Flying Dogs

Flying Dog's new Atlantic Lager

Our last beer tasting of the season. Flying Dog Brewery is our sponsor this evening and we will be tasting 3 of their wonderful beers. Ben Wiser from the brewery will be Flying Dog’s representative aboard the Woodwind this evening. Always fun and entertaining it is a pleasure to have Ben aboard. And what a … Read more

History Mondays are History….

Lauren at the wheel of Schooner Woodwind

  We had 3 great sails today. The winds were a little fluky in the river in the morning but by the last 2 sails it had settled down to a steady direction from the north and the sailing was fantastic. We had fun people out all day. The group sizes are getting a little … Read more

Girl Scouts sailing with Wooden Sailing Yachts

1888 Sailing Vessel "Elf" sailing with all of her sails up

Our first cruise was a Junior Girl Scout Program where we teach the girls how to sail the boat and work as a team on the Schooner Woodwind. The first lesson for them to learn was how to communicate. Picture all the girls learning the commands and nautical terms for sailing. We had them split … Read more

Hospice Cup Racing

Donnybrook (80+ foot race boat) sailing through the fleet of Hospice Cup

Today we had a fun-packed schedule of sailing cruises. And it was so nice that the wind wanted to contribute to the day! Our first cruise, we were asked to be a spectator boat for the Hospice Cup. A regatta to fund raise for 3 different Hospice programs in the area. We had the Montgomery … Read more

Fun Day on the Water….

Connie sailing and celebrating

I think the weather has something to do with it, but everyone seems to have a spring in their step and just be in overall good mood. The day was awesome. We had great wind a fun crew and wonderful guests all day. Our 1st sail started out with several frequent sailors joining us for … Read more

Amazing Sunset

Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

Today we had 2 sails on Woodwind II. A crew match race with the other Woodwind and a sunset shmooze cruise with dinner. For the Crew Match Race, a client privately charters both boats and we have the guests help us to win the race. We will have them switch their weight, tack the fisherman … Read more

Wild & Windy

Sailing with lots of wind under the US Naval Academy Bridge. Photo taken by Joshua McKerrow from the Capital Newspaper. (It was on the front page!)

The forecasts for today was a small craft advisory in the morning, then a gale warning for the afternoon, and then strong storms near 5:00. We had a 12:30-5:00 team building program where the clients learn how to sail the schooner and then race against their other team. With these wind conditions, Mike (the other … Read more

Small Craft Advisory?

Small Craft Warning Beer aboard the Schooner Woodwind

The only sail that we had today was a private event for the Heavy Seas Brewery! It was a sunset sail with full dinner and dessert. Sounds perfect… add in a Small Craft Advisory into the weather, and this makes it even more fun. As Hugh (owner of brewery) boarded the Woodwind, we joked how … Read more

Schooner Woodwind
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