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

Girls Just Want To Have Fun

Three ladies smiling and steering the schooner together

Our friend Laura is getting married, so we decided to do something fun together! It was a complete surprise when she found out that we are taking her on a sailing cruise. She was thrilled! The thee of us had a wonderful time, we had a chance to take over the wheel (under supervision of … Read more

Nephew Express

Group of five guests in blue t-shirts sailing the schooner together

I live in Annapolis and have no kids of my own, but managed to get my four nephews (one the wife of one nephew) to come to Annapolis for Memorial Day Weekend. It was the first time in 19 years that they were all together in one place! I wanted to share an experience unique … Read more

Just Showin’ Off

Four Blue Angel jets soaring over the schooner and water

The Blue Angels celebrate their return to Annapolis with a flyby for the Woodwind crew and guests in their famous diamond formation. Photo by Tom Lawrence of Baltimore, Maryland

A sailors dream.

Man and women steering the schooner together

We have been married for 15 years and she has been by my side every step of the way. Recently we chartered one of the most beatiful sailboats in the Chesapeake Bay, the Schooner Woodwind. Thank you for the wonderful memories you and your staff have kindly given us. May God continue to bless you, … Read more

A Day on the Bay.

Guests enjoying a breezy sunny sail on the schooner

Enjoying a 2-hour public sailing cruise on the Schooner Woodwind on the majestic Chesapeake Bay. Photo by Tony Hancock of Harrisburg, PA

Race to the Sun

Both schooners racing each other

This was taken at the Wednesday Sailboat races as the Woodwind and Woodwind II sail into some wonderful sunlight. Photo by Sabrina Raymond of Pikesville, Maryland

Schooner Woodwind
410-263-7837