Current Photo Contest Entries

I had a wonderful time on the beer tasting sunset cruise aboard Woodwind. The perfect mix of relaxation and site seeing. The local guides were also helpful pointing out areas of interest along the way. I will be back! Photo by Alicia Miller of Columbus, OH

40 of my closest friends came together to celebrate my 50th birthday! Photo by Kristin Duggan of Annapolis, MD

Sunset on the bay Photo by Ronda Duckworth of Charlottesville, Virginia

The special cruise was great being on the Woodwind II with Mickey, Adam & Paul. We've got some nice strong winds where we were able to lean the boat over for speed bursts. Scenery were great from typical powered boats to some regatta races of smaller sail boats. Photo by John chang of Gaithersburg, Maryland

Doodle: boat on the water in front of the tower Photo by Sean McDermott of College Park, MD

A bear and his ale on a sunset sail. Photo by Jordan Spangler of Ellicott City, MD

A day on the bay Photo by Gregory Blakey of Baltimore, Maryland

Katie and Caroline Tucker steer the Woodwind II on Father’s Day 2026 in Annapolis, MD Photo by David Tucker of Olney, Maryland

Father’s Day kisses aboard Woodwinds Photo by Alexandra Brooks of Columbia, MD

Perfect way to spend Father’s Day Photo by Alexandra Brooks of Columbia, MD

Selfie Photo by Lily Lerman of Aldie, Virginia

father’s day cruise!! Photo by Aliana Boniface of Keedysville, MD

I took Dad on this Woodwind sailing cruise as a gift for Father’s Day. It was his first time sailing and he wanted us to take a turn steering. He was happy! Photo by Toni Staub of Hanover, PA

Fun at the helm on the Woodwind! Photo by Robbin Whitley of Roanoke, Virginia

June on the water Photo by Sadee Weil of Alexandria, Va

Terry’s bach hijacks the boat!! Photo by Sonali Gupta of Olney, MD

Happy day! Photo by Beth Srour-Williams of Arnold, MD

Beautiful day for an afternoon sail by the Naval Academy Photo by Beth Srour-Williams of Arnold, MD

Enjoying our first time in Annapolis! Photo by Emily Moses of Washington, DC

Piloting the Woodwind II Photo by Kerry Branick of Rockville, 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