2024 Sailing Season is coming! See you April 13, 2024!

Avatar photoCaptain 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.

Is this the same schooner?

Sailing on the Woodwind

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 … Read more

Celebrations Aboard!

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 … Read more

You Know it’s Windy when…

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

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 … Read more

America, the Beautiful

Blue sky sailing on a strong breeze in front of the Bay Bridge

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 … Read more

AAA came for a visit of Annapolis

Sailing into the sunset on a Schooner close to dusk

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 … Read more

Good Morning Annapolis Harbor

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

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.

Dreams Come True

Couple with sunglasses on steering the schooner

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 … Read more

The Start of a Race means everything

Racing schooners

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.

Thumbs Up to Opening Weekend

First day of sailing on Woodwind

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 … Read more

Sweet Racing and Sunsets

Woodwind sails by just before the sun sets.

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 … Read more

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