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

Our Day Today…..In The rain….

Guests enjoying Rain, Wind and Beer..Oh what a night

We started the day off with a 5 hour charter from Annapolis to Cantler’s Crab house and back. While sailing up to the Chesapeake Bay Bridge on the way we saw the Kalmar Nyckel sailing under the center span toward us. What a fun sight. Sailing under the bridge is always fun…. Here is a … Read more

The Start of the Great Chesapeake Bay Schooner Race…..

Four Schooners at the start of The Great Chesapeake Schooner Race

Go Woodwind…!!!!   Competing in her 21st race Woodwind got off to a good start today. We were out there on Woodwind II with a boat load of well wishers. The conditions were in Woodwinds favor with lighter winds coming from the south making it and upwind race to start. Woodwind does well in the … Read more

Classic Boat Regatta

Elf Schooner moves swiftly by in the light breeze

The Fifth Annual NSHOF Classic Sailboat was held Sunday.  It was sponsored by the National Sailing Hall of Fame which is adjacent to City Dock.  What a great event!  What makes this event unique and special is that all the boats are made out of wood.  No “plastic fantastics” here.  There are many reasons to marvel … Read more

Star Spangled Sailabration

The Lynx is rigged similar to the Pride of Baltimore II. The original Lynx was a privateer built in Fells Point and was used during the War of 1812. Notice her split lower square sail on her foremast.

This past weekend was the 200th anniversary of the Battle of Baltimore which took place Sept 12 – 13, toward the end of the War of 1812.  It was one of the most significant battles of the war.  Francis Scott Key witnessed the event from on board a British warship while trying to secure the … Read more

Today on the Bay…..

Woodwind caught in the sunlight

We were lucky on our 1st sail today to time our arrival near the leeward mark just right to see both of the downwind legs in the J80 North American Championships. Look at all the fun spinnakers coming down wind to the mark with the bay bridge in view behind the fleet. Got right up … Read more

Stacey’s First Sail, Dramatic Sky

The threatening cloud points directly at Woodwind under jib and main.

Sunday, the southwest wind  blew between 15 to 20 knots, producing ideal sailing conditions.  We tacked out of the harbor and then eased our course and toward the Chesapeake Bay Bridge.  Stacey had never sailed before, but she enjoyed the experience so much that she asked to take the helm a second time.  Later in … Read more

History Monday and More……

Another beautiful sunset over Annapolis

What a great day on the water we had today. We had lots of fun families join us and we put them right to work. And they did a great job. After helping with the sails they came back to the wheel and helped me steer the boat as well. Thank you guys for doing … Read more

Anyone Can Sail When It’s Sunny…….

Welcome to the Woodwind Adventure.

But it takes a special type of person to come sailing when it’s raining. And that is exactly what I kept telling everyone all day as the rain continued to fall. But the winds were great and the sailing fantastic and all had a good time. The rains didn’t come until the 2nd sail of … Read more

Schooner Woodwind