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

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

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

Light Winds and History….

Young man in sunglasses at the helm of the Schooner Woodwind

The day started off with a good amount wind and the 1st trip was a 3 hour charter and we sailed all the way down to the Thomas Point Lighthouse. It is always a treat to have the right wind direction and speed to make it down here and back, it was nice to have … Read more

Rainy Day Tuesday……

Guest sailing the schooner with a bright green poncho on a stormy day

The 100% chance of rain didn’t scare these guys off. They came prepared with their own ponchos. Mom’s birthday was going on no matter what the weather gods said and we went sailing. Mom and Dad had been out with us 10years prior to celebrate another birthday with us and decided to return and bring … Read more

Another great day on the Bay…….

Young boy helps raise the Stay Sail

The wind was almost non-existent today, but that did not stop us from having a great day. We started out the day with the sighting of one of the beautiful yachts that lives here in Annapolis part of the year. The S.S. Sophie. She steamed passed us as we were setting sail and heading out … Read more

Monday and it still feels like the weekend……..

Erinn at the helm of the Schooner Woodwind

The boat was full most of the day and it felt like we were operating on a Saturday or Sunday. FUN…Lots of people and good sailing to boot. Erinn and her grandfather came out for a sail today and this was her training run. Erinn’s grandfather operates a couple of ships in the Caribbean and … Read more

94 years young….

Gentleman in white hat and blue shirt at the helm of Schooner Woodwind

I hope when I am a retired sailor that I have the spunk and energy of Evan Bostdorf. Celebrating his 94th birthday he came out with us today with family and friends and won the hearts of all. It was a pleasure to have you aboard. Happy Birthday Evan!!! It was awesome day on the … Read more

Schooner Woodwind