Captain Jennifer

About Captain Jennifer

Sailing has been a vital part of Jen's life since she was 5. Racing and cruising with her family filled her summers until she started teaching kids to sail. Her sophomore year in college, she sailed the Caribbean on a 125-ft schooner for credit in science, literature, and history. She now was addicted to schooner sailing. 3 years later, her family built the Woodwind. At 26, she became a captain.
Author Archive | Captain Jennifer
After the sunset, the skies above the Chesapeake Bay Bridge turned into Cotton Candy.

July 28, 2013

Local Everything aboard the Woodwind II

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I wish I had my better camera aboard! So, if you were on this cruise, seeing this post, please send me some pics. Many of my pics came out blurry. Local Everything…. what does that mean? To me, it means getting as much things locally sourced as you can and presenting it all on a …

Millie sailing Woodwind II while "racing" Woodwind back into the harbor.

July 27, 2013

All Smiles on Woodwind II

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Temperatures were in the low 80s, winds were blowing around 15 knots all day, and interesting clouds kept the sun from shining directly on us. We had four really fun sails, and we were able to sail to the Bay Bridge and back on 2 cruises. The other 2 sails we sailed completely across the …

July 18, 2013

“It’s so much Nicer on the Bay”

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Everyone was amazed what a nice breeze could feel like on a hot summer day on the Chesapeake Bay. We had a great private, corporate event on the first cruise. They loved the relaxing sail, and were anticipating the amazing crabs at Cantler’s Crab House. The second cruise was terrific, especially when four year old …

Jack Sherwood and Captain Jen

July 17, 2013

Heat Wave on the Woodwind

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It has been hot these past days! There was a little wind today which made us have a nice day. Our first cruise was a corporate team event where High’s Convenience Stores chartered both Woodwinds for a Crew Match Race. We got our teams ready on the fisherman sail winches and our other stations. There …

Storm clouds with the golden glow of sun on the other side of the storms.

July 7, 2013

Breeze On

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As soon as we set sail, and sailed beyond Horn Point, we knew today was going to be full of breeze and fun.  We had half filled boats for most of the day because of the heat. But with heat, it brings on the breeze on the Bay. So the people who sailed with us …

Donna & Scott Richardson

July 5, 2013

First Dates, Birthday and Alligators?

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Predictions for a breezy afternoon came true!  Great winds on all the sailing trips made for a terrific day of sailing on the Bay. On our first cruise, we scooted nicely under the Bay Bridge and back. As we headed to the bridge, one of the passengers, Donna, said to me. “It is so great …

Fireworks over Annapolis

July 4, 2013

Happy Independence Day

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Wind on July 4th?? With no threat of rain?? Delightful! We had 2 great sails to the bridge and back! And then we found a great spot to watch the fireworks, they were really great this year. And, in typical Annapolis fashion, there were 5 or 6 leftover fireworks from the finale that they shot …

Racing into Annapolis Harbor

June 20, 2013

Perfect night on the Woodwind

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  We had just one sail today on the Woodwind, the other boat had all four cruises, but we only had one. Tonight was a private event, I call it a shmooze cruise. Well the weather and breeze could not have been any better for saying thank you to your best customers. We put up …

Another beautiful sunset from the Woodwind.

June 19, 2013

It’s Not Always about Going Fast and Racing…

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We had a very light wind day today on the Woodwind. And we had a 4.5 hour private event for employees and their families of a nearby engineering firm. They brought a bunch of kids that were very inquisitive. We did our very best to keep them happy and into the sailing even though we …

Beautiful sunset on USNA

June 17, 2013

Monday Funday!

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We had such a nice, small cruise on the 11:00 sail on Monday. Our crew member Frank wanted to show the kids aboard how to navigate by using a chart. Hayden, was very intrigued by the entire process. Frank showed him how to triangulate a position using lines of position and how to use a …

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