Current Photo Contest Entries

Sailing with jen Photo by Rachel matthews of sykesville, MD - Maryland

Sailing 4th of July weekend Photo by Rachel matthews of sykesville, MD - Maryland

A photograph of Michele and Michael as they set sail for their intimate ceremony with their closest family and friends. Photo by REBEKAH STOLTZFUS of Gordonville, PA

My son helping steer the boat. Photo by Kelly Day of San Diego, CA

Under the Bridge Photo by Karin Roseman of Greenville, DE

Newlyweds on the Woodwind Photo by Ben Silvian of Arlington, Virginia

Cheers! Photo by Gwen Fine of McLean, VA

Sail>power Photo by Babs Kramer of Annapolis, MD

Stephen Kramer at the helm for his birthday outing! Photo by Brittney Kramer of Washington, DC

Sailing! Photo by Rebecca Headley of Birmingham, AL

Have a great time!! Photo by Robert Corbitt of Mount joy, PA

Sailed on 28 June. Great experience! Photo by Matt Diaz of Annapolis Junction, MD

Woodwind sail stormy night. Photo by Tricia Gatto Sears of Pompano Beach, FL

Riding with the captain Photo by Andrew Wotring of Baltimore, MD

Sail away under bridge with passengers and cruise Photo by Odutola ODUTOLA of Windsor Mill, MD

Great friends great time. Very fortunate to call my work colleagues friends! Photo by Brian Zuchelkowski of Albany, NY

Returning in sister schooner Photo by Lynda Cooperrider of Hinckley, Ohio

A fun little move at the start of our sailing adventure. Photo by Eliot Crandall of Webster, FL

Sunset cruise photo of Woodwind II returning to dock Photo by Melissa Bilyeu of Clayton, NC

What a great beer to celebrate our sail! Photo by Stefanie McAnally of Wayzata, MN

Taken on fall boat show sail Photo by Heather East of Annapolis, MD

Happy Sailing! Photo by Chris Bolton of Hagerstown, MD

Sails in the breeze! Photo by Chris Bolton of Hagerstown, MD

This 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

Four 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

A young girl’s first time at the helm with guidance from Captain Delaney. Photo by Barbara Berry of Worthington, Ohio

Best friends having a great afternoon on Woodwinds II Photo by Sharon Gatt of Annapolis, Maryland

Picture 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

Captain Jen leading Junior Captain Kristin! Photo by Dan Sheehan of South Bend, IN

This 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

Captain Mickey and trainee Michael Photo by Emily Seltzer of Philadelphia, PA

Photo of the Woodwind II's blue flag under sail Photo by Barbara Brawn of Annapolis, Maryland

Our sail Photo by Mary Karen Engel of St louis, Mo

33 years! Lovely trip! Photo by Jeff Siegler of Long Branch, NJ

Fantastic day today Photo by David Dannemiller of Arlington, VA

Between the Bay twin spans pointing east. Photo by Ken Smith of La Plata, MD

Windy Day on the Bay Photo by Ken Smith of La Plata, MD

I just moved to Annapolis. I am a senior citizen and LIVING MY LIFE! Photo by Janet Walker of Annapolis, MD

Enjoyed the trip! Thank you! Photo by Rudolph Uebersezig of Leesburg, VA

Schooner races Annapolis to Norfolk Va 10/3/24 Photo by Jennifer Crews-carey of Annapolis, Maryland