Schooner Woodwind

Now Sailing for the 2026 Season — Book Your Cruise Today!

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

Off to the Starting Line

Both schooners side by side at starting line

The Woodwind and Woodwind II are heading off to the starting line of the Wednesday Night Sailboat Races in Annapolis. Photo by Sabrina Raymond of Pikesville, Maryland

Woodwind 1

Schooner sailing along in a stiff breeze

WW1 passing by us at the blue angel practice Photo by kernie Harkleroad of annapolis, md

Our star to sail her by

Grey and yellow sunset cruise

Taken Saturday evening during Memorial Day weekend on the sunset cruise of the Woodwind II. The winds may have been light, but the sunset and all the ship’s company was perfect. Photo by Jason Weyant of Sterling, VA

Woodwind at Sunset

Calm waters reflecting sunset sail

My wife and I were enjoying our first sunset sail on the Schooner Woodwind in May of 2014. I caught this while sailing back to shore. Photo by Joseph Hjelmgren of Aubrey, Texas (TX)

Spray

Water Spraying up over the deck looking through to Thomas Point Lighthouse

I was attempting to take a picture of the lighthouse and at the precise moment when I took the shot a spray of water appeared. Photo by Harlan Shafer of Parkville, MD

Let the sunset lead you home

Delft Blue and pink skies over the schooner sailing on blue waters

From Woodwind II of the Woodwind, just outside of Annapolis harbor, Saturday evening of Memorial Day weekend. To borrow the words of a son of a son of a sailor, “It’s been a lovely cruise.” Photo by Jason Weyant of Sterling, VA

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