Schooner Woodwind

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

HipNautic

Sailboats moored in the harbor at dusk

Mesmerizing view sailing back to the inner harbor in Annapolis on the Schooner Woodwind Sunset Cruise ⛵️ Photo by Rachel Brennan of Arlington, VA

Competition

Peering through the schooner steering wheel at 2nd schooner

Competition racing from Wed, Aug. 24th, 2016. Picture taken through the helm when we were in the lead. Photo by Darla Powell of Annapolis, Maryland

Sails Up

White sails, rigging and mast against a bright blue sky

8-3-16 Woodwind II Cruise Sails up Photo by Michael Mayhew of Glen Burnie, Maryland

Woodwind @ sunset

Sunset with rays of sun peaking through clouds over Annapolis

Watching the Woodwind eat Woodwind II’s dust and the beautiful sunset was the icing on a great day in Annapolis! Photo by Sara Pletcher of Milford, DE

So Many Sails

Schooner sailing among many sailboats on the bay

Wednesday night sail boat races on 8/3 were immensely enjoyable, particularly when Woodwind II beat Woodwind to take the summer lead 7-6! Photo by Sara Pletcher of Milford, DE

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