2025 Photo Contest Entries
Welcome to the 2025 Sailing Season!
-
PLAY VIDEOPure happiness as we take a sibling sail!❤️ Photo by Erika Houska of Wadsworth, Ohio -
PLAY VIDEOTook this as we were pulling back into the harbor. It was a calm night and a pink sky. Photo by Valerie Davis of Annapolis, Maryland -
PLAY VIDEOI took this when I went on a sunset sail. It was my first experience getting out on the bay! Photo by Valerie Davis of Annapolis, Maryland -
PLAY VIDEO -
PLAY VIDEOCelebrating our wedding aboard the Woodwind II Photo by Michele Russell of Raleigh, NC -
PLAY VIDEOAn awesome Sail on the Woodwind to my favorite Lighthouse, Thomas Point Shoal Lighthouse. 10/5/2025 Photo by David Sites of Riva, Maryland -
PLAY VIDEOA guest steers the boat. Photo by Jessica Allison of Severna Park, MD -
PLAY VIDEO -
PLAY VIDEOIt was our very first time sailing together ⛵️ The crew was incredibly kind and helpful, letting us raise the sail ourselves and really experience it hands-on. With the clear blue sky and the cool breeze, it turned into an unforgettable day 💙 Photo by Ye seul Cho of Rockville, MD -
PLAY VIDEO -
PLAY VIDEOMy eleven year old son enjoying steering the boat. Photo by Bryan Jones of Millsboro, Delaware -
PLAY VIDEO -
PLAY VIDEO -
PLAY VIDEOI like to take photos from unusual angles. This photo of the sail and the clouds speaks to me of the freedom of moving in quiet on the waters Photo by Sandra Miller of Lansdale, PA -
PLAY VIDEOStitching on the sail on a beautiful fall day Photo by Sandra Miller of Lansdale, PA -
PLAY VIDEO -
PLAY VIDEOPirates of Chesapeake 🏴☠️ Photo by Elizabeth Regan of PLEASANTON, CA -
PLAY VIDEO4 nurses reuniting in Annapolis Photo by Lucia Dallas of Beaverton, Oregon -
PLAY VIDEO
2024 Photo Contest Entries
-
PLAY VIDEOTaken on fall boat show sail Photo by Heather East of Annapolis, MD -
PLAY VIDEO -
PLAY VIDEO -
PLAY VIDEOThis summer, my family and I visited Annapolis and we enjoyed our time on Woodwind cruise. I brought Leica M3 with me and shot in Kentmere iso 400 film. Annapolis was melancholic, gentle and elegant in black and white. It gave a timeless look and feel that stayed with me. We appreciate this unforgettable experience and amazing and profressional crew behind it. Hope one day we could return to the cruise and document Annapolis port and beautiful people there. Photo by Chen-Pang Chang of Astoria, New York -
PLAY VIDEOFour weeks after elbow surgery. Nothing was going to stop me from enjoying some wine and sailing the bay! Photo by Susan Sturek of Ellicott City, Maryland -
PLAY VIDEOA young girl’s first time at the helm with guidance from Captain Delaney. Photo by Barbara Berry of Worthington, Ohio -
PLAY VIDEOBest friends having a great afternoon on Woodwinds II Photo by Sharon Gatt of Annapolis, Maryland -
PLAY VIDEOPicture of sailboat alongside Schooner Woodwind on afternoon cruise with sailing school boats on the background and sunlight dancing on the water and wake waves Photo by Sherry Bowman of Arlington, Virginia -
PLAY VIDEOCaptain Jen leading Junior Captain Kristin! Photo by Dan Sheehan of South Bend, IN -
PLAY VIDEOThis is my wife enjoying her spontaneous Sunday afternoon event 2 weeks after getting her sailors licence. She was more interested in the way the sails work than the beautiful Annapolis. It was a win anyway! Photo by Serhat Arslan of Istanbul, Türkiye -
PLAY VIDEOCaptain Mickey and trainee Michael Photo by Emily Seltzer of Philadelphia, PA -
PLAY VIDEOPhoto of the Woodwind II's blue flag under sail Photo by Barbara Brawn of Annapolis, Maryland -
PLAY VIDEO -
PLAY VIDEO33 years! Lovely trip! Photo by Jeff Siegler of Long Branch, NJ -
PLAY VIDEO -
PLAY VIDEOBetween the Bay twin spans pointing east. Photo by Ken Smith of La Plata, MD -
PLAY VIDEO -
PLAY VIDEOI just moved to Annapolis. I am a senior citizen and LIVING MY LIFE! Photo by Janet Walker of Annapolis, MD -
PLAY VIDEOEnjoyed the trip! Thank you! Photo by Rudolph Uebersezig of Leesburg, VA -
PLAY VIDEOSchooner races Annapolis to Norfolk Va 10/3/24 Photo by Jennifer Crews-carey of Annapolis, Maryland
