2023 Photo Contest Entries
Sailing Season Starts April 15, 2023
Check back soon!
2022 Photo Contest Entries
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PLAY VIDEOLove to see sails full and the crew getting their Sail On! Photo by Krista Wallach of ANNAPOLIS, Maryland
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PLAY VIDEOMaking sure you don’t get boomed Photo by Brian Lieberman of Columbia, MD
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PLAY VIDEOMy husband and I in my new Helly Hansen, to brave the brisk Mother’s Day sail!! Photo by Shelagh Hafner of Lutherville-Timonium, MD
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PLAY VIDEOForever in need for some Vitamin Sea. Photo by Christine Johns of Haymarket, VA
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PLAY VIDEOSunset cruise 4/16 Photo by Susan Guiliano of Gilbertsville, PA
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PLAY VIDEOGreat Sunset Cruise returning to Port. Perfect weather and clear skies. Excellent Crew & great way to celebrate our 14th Wedding Anniversary! Photo by John MacCoy...
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PLAY VIDEOBeginning of a cruise on the Chesapeake Photo by Christian Michel of Gaithersburg, MD
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PLAY VIDEOParker in the Red Jacket with his questions & Captain Micky with his answers kept us laughing the whole cruise. Photo by JAMES WU of COLUMBIA,...
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PLAY VIDEOIt doesn’t Rain In Woodwind Sailing ⛵️. It rains On Woodwind Sailing⛵️. Photo by James Wu of Columbia, MD
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PLAY VIDEOA beautiful afternoon with a nice breeze on the Woodwind ! Photo by Sarah Schaefer of Edgewater, Md
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PLAY VIDEOWe sailed on a perfectly beautiful day and saw a beautiful Sun set behind the sails of Woodwind 2. Photo by Eddy Vleugels of Annapolis, MD
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PLAY VIDEOSunset as seen through the rigging on the starboard side of the ship. Photo by Deborah Mulligan of Annapolis, Maryland
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PLAY VIDEOWoodwind at dusk with red and pink hues. Photo by Deborah Mulligan of Anna, Maryland
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PLAY VIDEOSailing at the end of the day just as the sun set. The reflection was the Woodwind sister ship. Photo by Deborah Mulligan of Annapolis, Maryland
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PLAY VIDEOChampagne sails on the Woodwind I. Cheers to Captain Jen! Photo by Danielle Autieri of Philadelphia, PA
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PLAY VIDEOSunset sail view of downtown Annapolis Photo by My Nguyen of Edgewater, md
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PLAY VIDEOIn their first ever sailboat ride, they got to raise the sails and it made it even more special! Photo by MIA Mckitterick of Lees summit,...
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PLAY VIDEOPicture taken from WoodWind on Sunset cruise (May 29th) Photo by Mandy Decker of Edgewater, MD
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PLAY VIDEOLear one about the golf course they don’t need Photo by Gretchen Houk of Sulphur Springs, Texas
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PLAY VIDEOSchoonerWoodwind Lover! Thank you! Photo by MariaPaz Ribadeneira of Chicago, Illinois
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PLAY VIDEOSails floating in the clouds. Photo by Sean Valis of Annapolis, Md
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PLAY VIDEOMy kids and I had a great time sailing yesterday. Thanks for making our first sailing experience a good one. We will be back. Thanks...
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PLAY VIDEODavid & Anna aboard the Woodwind with their wedding party, kicking off their wedding weekend celebrations in Annapolis. Photo by Anna Fell of Berwyn, PA
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PLAY VIDEOCaptain of the Woodwind Photo by Nusaybah Abo-Issa of Springfield, Va
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PLAY VIDEOCelebrating 47 Years of sailing together. With friends CAPN Mickey, Stephanie, Ali and Sophia. Photo by Steve Whelan of Gaithersburg, MD
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PLAY VIDEOJune 8, 2022. 11:00 cruise. I took this photo lying on the seating area and looking up. The photo does not really give the view...
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PLAY VIDEOOsprey chick in nest on channel marker, wrapped up in vegetation like a baby blanket! Photo by Wendy Crowe of Glen Burnie, MD
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PLAY VIDEOCelebrated dads 60th with an amazing Schooner sail! Thank you schooner crew! Photo by Aubrey Lerner of Santa Monica, CA
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PLAY VIDEOFirst time on a sailboat and someone let this kid drive! Photo by Tina Terranova of Ellicott City, Maryland
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PLAY VIDEOA symbol of how the US is unprecedentedly divided Photo by Grazia Mieren of Annapolis, Maryland
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PLAY VIDEOTaken June 29 on Schooner Woodwind II Wed sailing race. Woodwind I made a questionable turn when we had ROW. Photo by Rosalie Galante of Lewes,...
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PLAY VIDEOBeautiful sunset photo of the Woodwind II Photo by Deborah Mulligan of Annapolis, Maryland
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PLAY VIDEORounding the buoy in the Wednesday night race. Photo by Paige Berkebile of Belmont, NC
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PLAY VIDEOEnd of the Race – Sunset through the Rigging Photo by Deborah Mulligan of Annapolis, MD
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PLAY VIDEOSailing on Monday June 27 in a down pour while singing Photo by Lisa Rahman of Oxon Hill, MD
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PLAY VIDEOSam watching the sails Photo by Casey Wenrich of Colorado Springs, Colorado
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PLAY VIDEOTaken of the sunset tour shorty after the captain took the helm. Photo by Mason Sullivan of Rosemount, MN
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PLAY VIDEOPopPop Kevin’s Birthday Sail Photo by Felecia Fischell of West Hills, CA
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PLAY VIDEOWe were offered by Captain Jen to hold the fort while we were facing high wind and two of our colleagues went ahead at the...
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PLAY VIDEOPop-Pop Kevin’s 69th Photo by Felecia Fischell of West Hills, CA
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PLAY VIDEOBringing the boat back to dock at sunset Photo by Katie Nicholos of Washington, DC
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PLAY VIDEOLadies day that became a bit hairy Photo by Allison Sherman of Washington, Dc
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PLAY VIDEOCaught the Woodwind II from City Dock after we took an earlier sail. Photo by Jonathan Haber of Rockville, MD
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PLAY VIDEOA photo of the crew “manning” the sails Photo by Jonathan Haber of Rockville, MD
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PLAY VIDEOMy wife n I watching the Capt. Work the hard winds ! Photo by Den Stallings of Columbia, Md
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PLAY VIDEOSailing two stars to the right and on until morning Photo by tom Lanyon of annapolis, md
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PLAY VIDEOWoodwind one from Woodwind 2 Photo by William Kraus of Edgewater, Maryland
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PLAY VIDEOThe end of a beautiful sail on the Woodwind I with the storms all around us. It was a wonderful night with gentle winds, history...
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PLAY VIDEOTo conclude our wedding weekend in Annapolis, we thought renting one of the Schooner Woodwind boats would be the perfect way to end what turned...
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PLAY VIDEOAmazing , shot of us sailing into the sunset. We had a great time and would definitely do it again. Photo by Cathy Scarborough of Baltimore,...
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PLAY VIDEOBachelorette party Photo by Brittany Hogan of Severna Park, MD