Author Archive | Captain Jennifer


The Start of a Race means everything

It was an exciting start to the Wednesday Night race this week. We just finished our rules seminar with J World Sailing School, so we ready to practice using the rules. See all the photos on our Facebook page.

First day of sailing on Woodwind

Thumbs Up to Opening Weekend

The day has finally arrived! The boat is shiny and beautiful, fresh out of winter maintenance work and it is time to actually sail! Even though, the first day of sailing was yesterday… it was my first day of sailing today. We had great winds around 15 knots and sailed almost to Thomas Point Lighthouse […]

Woodwind sails by just before the sun sets.

Sweet Racing and Sunsets

What a beautiful Saturday! When I saw how much wind was out there, I knew we could make it to see the J70 North American Championships being held in the middle of the Bay. This was my goal for the day. I wanted show guests a starting line with 90 boats on it, but had […]

Sailing into Annapolis for Sunset

Oh what a beautiful Sunset

Two blogs today for me! Our sunset sail was really nice. We had a family celebration of the marriage of Mr. and Mrs. Bull. They brought aboard a tiny 3 month old, who was quite adorable (and a life-jacket). She wouldn’t give up the wheel. We had a great sunset with Woodwind sailing past the […]

Cliff sailing the Woodwind to Cantler's Crab House

The Best Charter Guests EVER

This may sound like a challenge to all of the other private charter groups  that have sailed on the boat, and all the ones that are upcoming, but it is not a challenge. It is a reflection of how nice people can be to their fellow employees, our crew and waitstaff at the restaurant they […]

Drew Baker talks about Old Westminster Wine

Wine and the Wind

We had two cruises today and they were total opposites of each other. The first cruise was a girl scout cruise of mostly teen aged girls. They learned about sailing, navigation and the Chesapeake Bay ecosystem. Each girl would go to all three stations where the crew would engage them in fun discussions and show […]

Woodwind Sailing under the Bay Bridge

Pictures tell 1000 words

Beautiful day of sailing! The day started with a successful team-building program for a local company in the morning. They learned how to sail around buoys and navigate safely in the Bay, while using great communication. On our second sail, we took out another private charter for a regional office outing. The wind picked up […]

Another pretty sunset over Annapolis

Magical, Musical Cruise

Pretty lucky weather we are having here in Maryland. We have had cool, dry conditions for the past 3-4 days and it has been gorgeous. We started the day with a private charter that had enough breeze to get under the Bay Bridge and back… well sort of. The wind died and changed direction a […]

Sailing the Woodwind

Seeing over the Steering Wheel

For Woodwind, we only had two sails today. A 3:00 and a sunset sail at 5:30. Both were public cruises. On the first sail there was a nice size birthday party, and on the sunset sail we had a Air Force retirement party of about 20 people. If course there were other guests aboard, these […]

Claudia having fun sailing

20 Years Ago…

It is so amazing to me that my family started Woodwind twenty years ago. Every so often I am reminded of how long ago it was, although sometimes it seems like yesterday. Read on and you’ll see where I am going with this. Thursday’s sails were incredible. The first sail, now at 12:30, we sailed […]

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