Current Photo Contest Entries

This image is everything! It includes the Chesapeake bay as well as shows how amazing this boat really is! Photo by Rachel Beckman of Mount Airy, MD

Layla Robinson taking a turn steering the sailboat toward the Bay Bridge. Photo by Jim Robinson of Middletown, Maryland

Our most memorable wedding day on April 19, 2026! Photo by Nao Gamo of Greenbelt, MD

View from the deck at the start of sailing Photo by Julie Cross of Saint Louis, MO

Finn’s turn to steer! Photo by Julie Cross of Saint Louis, MO

Red, White, and Chesapeake Blue 🇺🇸 Photo by Katie Fisher of Cherry Hill, New Jersey

Black and white photo of the sails of the woodwind 2 Photo by Amarilis M of Severna Park, MD

My wife, Maddie, enjoying some wine amidst a downpour Photo by Charlie Carita of Washington, DC

Woodwind sailboat in Annapolis! Photo by Niloo Kamali of Leesburg, VA

Photo of us driving the boat Photo by angela bowes of philadelphia, pennsylvania

Sailing present from my wife. Saw this boat several times and finally went out. Excellent time! Photo by Jim Manning of Pittsburgh, pa

Sailing where the wind takes us Photo by John Folger of Pittsburgh, PA

A bridge with a beautiful sunset Photo by Lionel Schoenbauer of Washington, DC

Tricolor spinnakers inbound Photo by Robert Woods-Corwin of Vienna, VA

Boat behind us in the reflection of the sun Photo by Mackin Lofaso of Rochester, NY

Two thumbs up for sailing in a downpour. Photo by Eric Phillips of Arlington, VA

14 year wedding anniversary 🙂 Photo by Grady Wise of Royersford, PA

Aug 3, 2026 the sky turned pink for us over the beloved Greenbury Point! Photo by Sue Steinbrook of Annapolis, Md

Just another lively night on the Schooner Woodwind, HDR photo that I captured at sunset. Photo by Sue Steinbrook of Annapolis, MD

Atticus learns how to sail. Photo by JESSICA ORR FLINCHUM of Brandywine, MD

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