Current Photo Contest Entries

Love to see sails full and the crew getting their Sail On! Photo by Krista Wallach of ANNAPOLIS, Maryland

Making sure you don’t get boomed Photo by Brian Lieberman of Columbia, MD

My husband and I in my new Helly Hansen, to brave the brisk Mother’s Day sail!! Photo by Shelagh Hafner of Lutherville-Timonium, MD

Forever in need for some Vitamin Sea. Photo by Christine Johns of Haymarket, VA

Sunset cruise 4/16 Photo by Susan Guiliano of Gilbertsville, PA

Great Sunset Cruise returning to Port. Perfect weather and clear skies. Excellent Crew & great way to celebrate our 14th Wedding Anniversary! Photo by John MacCoy...

Beginning of a cruise on the Chesapeake Photo by Christian Michel of Gaithersburg, MD

Parker in the Red Jacket with his questions & Captain Micky with his answers kept us laughing the whole cruise. Photo by JAMES WU of COLUMBIA,...

It doesn’t Rain In Woodwind Sailing ⛵️. It rains On Woodwind Sailing⛵️. Photo by James Wu of Columbia, MD

A beautiful afternoon with a nice breeze on the Woodwind ! Photo by Sarah Schaefer of Edgewater, Md

Captured Sam in the Sun Photo by Eddy Vleugels of Annapolis, MD

We sailed on a perfectly beautiful day and saw a beautiful Sun set behind the sails of Woodwind 2. Photo by Eddy Vleugels of Annapolis, MD

Sunset as seen through the rigging on the starboard side of the ship. Photo by Deborah Mulligan of Annapolis, Maryland

Woodwind at dusk with red and pink hues. Photo by Deborah Mulligan of Anna, Maryland

Sailing at the end of the day just as the sun set. The reflection was the Woodwind sister ship. Photo by Deborah Mulligan of Annapolis, Maryland

Champagne sails on the Woodwind I. Cheers to Captain Jen! Photo by Danielle Autieri of Philadelphia, PA

Sunset sail view of downtown Annapolis Photo by My Nguyen of Edgewater, md

In their first ever sailboat ride, they got to raise the sails and it made it even more special! Photo by MIA Mckitterick of Lees summit,...

Picture taken from WoodWind on Sunset cruise (May 29th) Photo by Mandy Decker of Edgewater, MD

Lear one about the golf course they don’t need Photo by Gretchen Houk of Sulphur Springs, Texas

SchoonerWoodwind Lover! Thank you! Photo by MariaPaz Ribadeneira of Chicago, Illinois

Sails floating in the clouds. Photo by Sean Valis of Annapolis, Md

My kids and I had a great time sailing yesterday. Thanks for making our first sailing experience a good one. We will be back. Thanks...

Pro Team build. Photo by Jacob Lutes of Schaumburg, IL

David & Anna aboard the Woodwind with their wedding party, kicking off their wedding weekend celebrations in Annapolis. Photo by Anna Fell of Berwyn, PA

Captain of the Woodwind Photo by Nusaybah Abo-Issa of Springfield, Va

Celebrating 47 Years of sailing together. With friends CAPN Mickey, Stephanie, Ali and Sophia. Photo by Steve Whelan of Gaithersburg, MD

I have no words! Photo by Anne Fetsko of Annapolis, Maryland

June 8, 2022. 11:00 cruise. I took this photo lying on the seating area and looking up. The photo does not really give the view...

Osprey on Channel Marker #4 Photo by Wendy Crowe of Glen Burnie, MD

Osprey chick in nest on channel marker, wrapped up in vegetation like a baby blanket! Photo by Wendy Crowe of Glen Burnie, MD

Celebrated dads 60th with an amazing Schooner sail! Thank you schooner crew! Photo by Aubrey Lerner of Santa Monica, CA

First time on a sailboat and someone let this kid drive! Photo by Tina Terranova of Ellicott City, Maryland

Schooner at sail Photo by Nicole Grego of Drums, Pa

A symbol of how the US is unprecedentedly divided Photo by Grazia Mieren of Annapolis, Maryland

Taken June 29 on Schooner Woodwind II Wed sailing race. Woodwind I made a questionable turn when we had ROW. Photo by Rosalie Galante of Lewes,...

Beautiful sunset photo of the Woodwind II Photo by Deborah Mulligan of Annapolis, Maryland

Rounding the buoy in the Wednesday night race. Photo by Paige Berkebile of Belmont, NC

End of the Race – Sunset through the Rigging Photo by Deborah Mulligan of Annapolis, MD

Sailing on Monday June 27 in a down pour while singing Photo by Lisa Rahman of Oxon Hill, MD

Riley taking the wheel. Photo by Wanda Forrest of Laurel, MD

Sam watching the sails Photo by Casey Wenrich of Colorado Springs, Colorado

Taken of the sunset tour shorty after the captain took the helm. Photo by Mason Sullivan of Rosemount, MN

PopPop Kevin’s Birthday Sail Photo by Felecia Fischell of West Hills, CA

We were offered by Captain Jen to hold the fort while we were facing high wind and two of our colleagues went ahead at the...

Pop-Pop Kevin’s 69th Photo by Felecia Fischell of West Hills, CA

Jib and a sunset Photo by Katie Nicholos of Washington, DC

Bringing the boat back to dock at sunset Photo by Katie Nicholos of Washington, DC

Ladies day that became a bit hairy Photo by Allison Sherman of Washington, Dc

Caught the Woodwind II from City Dock after we took an earlier sail. Photo by Jonathan Haber of Rockville, MD

A photo of the crew “manning” the sails Photo by Jonathan Haber of Rockville, MD

June on the Chesapeake Photo by Tara Orr of Erie, CO

My wife n I watching the Capt. Work the hard winds ! Photo by Den Stallings of Columbia, Md

Sailing two stars to the right and on until morning Photo by tom Lanyon of annapolis, md

Woodwind one from Woodwind 2 Photo by William Kraus of Edgewater, Maryland

The end of a beautiful sail on the Woodwind I with the storms all around us. It was a wonderful night with gentle winds, history...

To conclude our wedding weekend in Annapolis, we thought renting one of the Schooner Woodwind boats would be the perfect way to end what turned...

Amazing , shot of us sailing into the sunset. We had a great time and would definitely do it again. Photo by Cathy Scarborough of Baltimore,...

Navigating back to port Photo by Charles Young of Washington, DC

Bachelorette party Photo by Brittany Hogan of Severna Park, MD