Current Photo Contest Entries

Pure happiness as we take a sibling sail!❤️ Photo by Erika Houska of Wadsworth, Ohio

Took 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

I 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

Our wedding day! Photo by Michele russell of Raleigh, NC

Celebrating our wedding aboard the Woodwind II Photo by Michele Russell of Raleigh, NC

An awesome Sail on the Woodwind to my favorite Lighthouse, Thomas Point Shoal Lighthouse. 10/5/2025 Photo by David Sites of Riva, Maryland

A guest steers the boat. Photo by Jessica Allison of Severna Park, MD

Sunset Photo by Brittany Charity of Owings, Maryland

It 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

Freighter on the bay Photo by Ross Heisman of Annapolis, MD

My eleven year old son enjoying steering the boat. Photo by Bryan Jones of Millsboro, Delaware

Boat! Photo by Emma Anderson of Pflugerville, TX

Say Cheese! Photo by Sue Johnson of Birmingham, AL

I 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

Stitching on the sail on a beautiful fall day Photo by Sandra Miller of Lansdale, PA

Bay bridge Photo by Jill MacMillan of Arnold, Maryland

Pirates of Chesapeake 🏴‍☠️ Photo by Elizabeth Regan of PLEASANTON, CA

4 nurses reuniting in Annapolis Photo by Lucia Dallas of Beaverton, Oregon

CBB Photo by Karin Roseman of Greenville, DE

Between the Bridges Photo by John Bonanno of Wyomising, PA

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