2024 Sailing Season is coming! See you April 13, 2024!

Gusty Sails

Guests on board sailing away into the bright blue sky

It was the last day of the season and the last voyage of our captain. The skies were clear and the wind just right as we sailed out to the bridge, as we headed back there was calmness in the sails and everyone on board as we watched the sun start to sink into the … Read more

Date Night

Couple enjoying a sail from the deck of the schooner

My husband and I spending time after one of my last chemo treatments for stage 4 cancer Photo by Holli DIllard-Cranfill of Grasonville, MD

Helping

Guests lending a hand in raising the sails on board the schooner

First time ever on a boat Photo by Brent Cranfill of Grasonville, Maryland

Sails on the Bay

Looking through schooner sails at sailboats on the blue horizon

My husband treated me to a sunset cruise as a belated birthday gift because my happy place is on the water. It was a perfect evening! We were participating in the Wednesday night sail race in the tall ship category so we simply raced the sister ship-We Won… the captain was awesome and we had … Read more

Heading to the Harbor Sunset Sail

Schooner sailing by channel marker with Osprey nest and sunset behind it

I was sailing close to Woodwind I and II on a beautiful, breezy evening and just rounded the mark heading back to Annapolis Harbor while the sun was setting behind. Photo by Heather East of Annapolis, MD

Schooner Woodwind
410-263-7837