Schooner Woodwind

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

Teamwork

Raising the sails

It takes a team to raise the main sail! Photo by Seth Adams of Annapolis, MD

Sunset on the Bay

Couple in the sunset on the schooner

I found the perfect opportunity to take a picture that gives the viewer the mood of entire sailing trip: breezy, relaxing, romantic. Photo by Seth Adams of Annapolis, MD

Sailor’s Delight

Purple sunset sky above the sails

I wish I could say it was all in the editing, but the sky genuinely took on such a range of colors as we headed back to shore that evening. It didn’t seem to matter so much that we lost the race. Photo by Jenna Kanell of Atlanta, GA

Sunset will save me

Shot of the Woodwind II life preserver

sunset over the life ring during the sunset cruise on the Woodwind II Photo by Desiree Noel of Columbus, New Jersey

Schooners by the Academy on a beautiful Aug afternoon

Schooners by the Academy on a beautiful August afternoon

While sailing with friends on an Annapolis Sailing School Rainbow, we enjoyed watching both of your schooners sailing by the Naval Academy. It was a beautiful Saturday in August – with wind. Later, eating outside at Pusser’s, we sat in between where the Schooners were docking, too. Photo by Nancy DiPaolo of Arlington, VA

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