Current Photo Contest Entries

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

a picture of the boat Photo by Nina Dungee of Spring City, PA

Lovely time thank you! Photo by Susan Wadsworth of Ft myers, FL

I don’t think daughter #1 knew that daughter #2 was going into the drink! Photo by Anna Siefken of Pittsburgh, PA

Great Day on the Bay!! Photo by Anne Armstrong of Edgewater, MD

First time sailing! Photo by Ivy Triana of Annapolis, MD

Pink sunset with sailboats Photo by Nikki Williams of Glen Burnie, MD

Wedding party, bride and groom. Photo by Marc Andros of Houston, Texas

Wife took the wheel for a bit Photo by Matthew Maguire of Philadelphia, Pa

Having a fun sail Photo by Andrew Gallagher of Feasterville, Pa

Oliver is now 7! (I also posted the picture of him when he was 2.5years old) Photo by Katie Brandyberry of Lancaster, PA

Oliver is 2.5 years old! Photo by Katie Brandyberry of Lancaster, PA

Captaining the Woodwind II at golden hour! Photo by Dylan Crandall of Raynham, Massachusetts

Beautiful Sunset on the Woodwind Photo by Wendy Turczynski of Lewisberry, Pa

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