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
Sailing on the Woodwind

July 21, 2014

Is this the same schooner?

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The first conversation of the day started with, “Is this the same schooner?….” We get this question a lot, followed by “as used in the Wedding Crasher’s Movie?” But this was a different question… “as the one that was here, maybe 17 years ago?” I answered them, “yes it was, did you sail with us …

July 19, 2014

Celebrations Aboard!

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It was a day for celebrating!  We had three bachelorette parties aboard on 2 cruises.  They were all low key, and just wanted to spend their day sailing with their friends. On the sunset sail, we had a couple aboard Robin and (oh no… I forgot his name- I guess that’s better than writing the …

Lola, 5 years old, taking a turn at the helm

July 13, 2014

You Know it’s Windy when…

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You know it’s a windy, awesome day for sailing on the Woodwind when: Frequent Sailors’ are on each cruise and bring their friends (Russ, Joyce, Deb, Patrick, Pat, Ana, etc.) Frequent Sailors’ come by themselves because they are spontaneous and know a good sailing day when they see one. (Kathy) You have to tell guests …

July 4, 2014

America, the Beautiful

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Over this holiday weekend, it is easy to remember why we fought so hard to be our own country. What a beautiful country it is. And I am so thankful that I get to take people out sailing on the Woodwinds and introduce them to sailing. We had a terrific full weekend of sailing and …

Sailing into the sunset on a Schooner

May 19, 2014

AAA came for a visit of Annapolis

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AAA, the travel and media division- who write the books, and magazines came for a conference in Annapolis.  We wanted to show them a terrific time on the water, so we sailed them into the sunset! They loved Annapolis! Especially seeing it from the water. We were lucky to get some great photos of the …

Waking up aboard the Woodwind. The view from the Boat & Breakfast!

May 18, 2014

Good Morning Annapolis Harbor

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As the Captain of the Boat & Breakfast this weekend. I was delighted by the sky just after sunrise. I love waking up and seeing this view!  None of the guests were awake at the time, and it was a perfect moment to relax.

May 17, 2014

Dreams Come True

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Today was an exciting day!  The winds were beautiful and the temperature was mild. On every cruise other than the first one & sunset sail, we had a bachelorette party.  On the 1:30, we had two groups. On the 4:00, we had another one.  We made sure that the bride to be got a turn …


May 7, 2014

The Start of a Race means everything

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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

April 20, 2014

Thumbs Up to Opening Weekend

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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.

September 28, 2013

Sweet Racing and Sunsets

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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 …

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