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
Wednesday Night Racing on the Schooner Woodwind

July 25, 2012


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Today we had a 4 1/2 hour team-building cruise on the Bay. A company chartered us out to have their team have fun, but also work together. It was a nice small group of only 12 people, so after lunch, we started the training. It was very interesting to see how everyone got along and …

Wine in the Wind on Schooner Woodwind in Annapolis

July 22, 2012

Wine in the Wind

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What a terrific day! I love the wine tastings we do on the Schooner Woodwind! French Wines were the theme today, each “Wine in the Wind” has a different theme. Franck Agostino was the host today. And he knows wine. His job is the coolest job, I might add. He is from France and he …

Fun loving group from Cincinnati aboard the Schooner Woodwind II

July 21, 2012

Smiling in the Rain

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It was a rainy Saturday.  Everyone is calling, “are you still going sailing, even in the rain”? Yes, we sail rain or shine. Ponchos were handed out to everyone and the rustle of poncho plastic made each sail unique. We had wind, a nice breeze from the NE that had us doing about 8-9 knots. …

Woody, the grasshopper, goes for a ride on Schooner Woodwind

July 19, 2012

Friends and Mascots

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We always get the most wonderful people that sail on the Woodwinds! On our 11:00 sail, we only had 7 guests aboard. But they felt like friends immediately.  Dave was celebrating his birthday with his grandparents (almost 21st birthday) and he had a blast learning all about sailing. He was hooked into the love and …

July 18, 2012

Thank you Mother Nature

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Today was a very interesting day on the Woodwind. We had a team building for the first 2 cruises and then 2 public sails afterwards. One of those public cruises was the Wednesday Night Race. Thank you Mother Nature for 15 knots of wind from the SW! We had a good teambuilding with a company …

Sailing to Cantler's to enjoy a Maryland Crabfeast

July 17, 2012

Feeling Crabby

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We only had one sail today, a round trip private cruise to Cantler’s Crab House. This is my first cruise to Cantler’s on Woodwind this season so I was excited for it. The wind was blowing beautifully, 10 knots, from the NW as we gybed our way out of the Severn with about 35 guests. …

Amazing clouds building in the sky as we sailed around the Chesapeake all day

July 10, 2012

We needed the rain?

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As I walked down the dock this morning, schools of fish were everywhere. They were schooling in the most gorgeous way. This was so mesmerizing. It was a nice pleasant day on the water. Most of the boat traffic was from the 10 sailing camps on the Severn River. I may be exaggerating a little …

Sailing into the sunset on the Chesapeake Bay

July 8, 2012

Hot Summer Breeze

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All everyone was talking about was the heat… on Sunday, we were talking about the breeze. We had a nice breeze pick up from the NE. First cruise, we were able to sail around the US Junior Sailing Olympics. They had 3 different fleets out in the Chesapeake Bay. They had Lasers, 420′s and Optimist …

Chris and Kristin surprise proposal aboard Woodwind

July 6, 2012

“At least she said yes…”

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We were privately chartered for a special cruise tonight on our sunset sail. My cruise details said that we were having a surprise proposal happen. At 6:10, friends of Chris Wood and Kristen came to board the boat early for the surprise. They would be hiding below and come up when he pops the question. …

The Roadside Show Band playing on the Schooner Woodwind II

July 5, 2012

Foot Stompin’ Music

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What a hot day!!  The breezes were playing peek-a-boo with us. We had a delightful sail on our 11:00 sail with a cool breeze from the Bay. On the 2nd and 3rd cruise, the breeze was less consistent, but we found a way to keep cool with the 5th sail aboard. The D-Sail (diesel). By …

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