Current Photo Contest Entries

The wind was very strong, the water was rough, so captain Josh called for help! Photo by SERGIO PIMENTA of Belo Horizonte, MG

5/6/26 Photo by Zoe Forezzi of Albany, Ny

2 hr bay bridge tour. Perfect way to spend my birthday! Photo by Shannon Chapline of Catonsville, MD

Us Photo by Amy Riestenberg of Corinth, TX

First sail on woodwind. Great experience! Photo by Martin Niebrzydowski of Rockwood, Mi

At the helm of the Schooner Woodwind with Captain Jen! Photo by Fred Siebelts of Killingworth, CT

Good times! Photo by Fiorella Avalos of Woodbridge, New Jersey

May Day 2026 Photo by Andrea Colabella of Hoboken, NJ

Getting to steer the sailboat! Photo by Megan Lanphere of Sinclairville, New York

Weather bird Photo by Daniel Mayers of Frederick, MD

This is our third time sailing. We got engaged right before this and came here to celebrate! Photo by Kendall Connolly of Baltimore, MD

Photo of the sister ship at sunset Photo by Elizabeth Dare of Mullica Hill, NJ

Showing the new owners 59 North Off Shore sailing how a captain sails the boat. Just kidding. Loved the experience. Photo by Rob Ronk of Falls Church, Virginia

6 year old, Ian K., steering the Woodwind II, during his first sailing trip. Photo by Christopher Kwan of Lorton, VA

6 year old, Ian K., steering the Woodwind II, during his first sailing trip. Photo by Christopher Kwan of Lorton, VA

Nana visiting from Altoona, PA. Her grandson had a great time! Photo by Kara Burke of Severna park, MD

Having a great time! Photo by Rebecca Waters of Hubertus, WI

Take during the tail end of a bachelorette trip for our wonderful friend, Willing Photo by Kerrin Thomas of Boston, MA

We’re bonified captains now! Photo by Lacoya Heggie of Fredericksburg, VA

Spring sale 3pm 4/17/2026 Photo by Eric Denham of Scottsdale, AZ

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