Current Photo Contest Entries

4 yr old takes the high seas Photo by Amy Neff of Columbus, GA

Beautiful night for a sail—and race! Photo by Mark Porter of Davidson, NC

Raising the sail Photo by Tracy WOODSON of WILMINGTON, DE

Sunset photo taken at the bow Photo by Laney Gibson of Wayne, PA

A sunset photo off of the stern Photo by Laney Gibson of Wayne, PA

Aaron and Ilene Kohen Photo by Ilene Kohen of Virginia Beach, VA

Captain Mickey and Captain Aaron Photo by Ilene Kohen of Virginia Beach, VA

0.5 photo of me and my friend enjoying our time in woodwind with the sails in the background Photo by Aiden Burkett of Crofton, MD

A 0.5 of my friend and I looking at two of the sails aboard woodwind Photo by Aiden Moreno of Arnold, Maryland

Enjoying a windy day with a great crew Photo by Aurora Robeson of Brandywine, Maryland

Sippin’ & Sailin’ Cheers to the Chesapeake! Photo by Carlene Boyer of Alexandria, VA

It was half past 2 pm on a gloomy day when the swell came out to play. Photo by Marcus Frias of Washingon, Dc

A sailboat on the Chesapeake. Photo by Alyssa Ray of Severn, MD

Ahoy! Photo by Greg Rickers of Waverly, Ne

CRABby Saturday Photo by Mario Da Silva of WASHINGTON, DC

Koozies were super helpful! Photo by Dawn Parsons of Round Hill, VA

What a great day on the water with a great crew. Photo by Danielle Cherence of Red Bank, NJ

Racing to see who makes it back first Photo by Dawn Parsons of Round Hill, VA

A perfect day Photo by Kristen Nebel of Lancaster, PA

Right before we got onboard the schooner woodwind. Photo by Nikita Kachroo of DC, DC

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