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 to a Crabfeast at Cantler's Crab House on the Schooner Woodwind

August 14, 2012

Crabs, Beer, & Sailboat Racing (that’s what Annapolis does)

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Quoting a line from Wedding Crashers to make it appropriate here… but it’s so true! We sailed to a crab-feast, the guests had plenty of beer, and then 2 Maryland Breweries battled it out on the racecourse to see who would take home the Brewer’s Cup. All in a day’s work. The day started with …

Wine in the Wind, Woodwind in a glass!

August 12, 2012

Wine in the Wind

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Today was all about wine. “Wine in the Wind” is the name of our wine tasting cruises aboard the Schooner Woodwind. The region for this month’s tasting was Down Under Wines, New Zealand and Australia. Howard Dinkel from Bacchus Distributing was aboard to educate us about wines from this region and to explain about the …

Schooner Woodwind sailing fast in Annapolis

August 11, 2012

Great wind for 2 sails

Captain's Blog2 Comments

We had a terrific day today with 2 great, windy cruises. We hit over 10 knots. The guests aboard both of our cruises really appreciated that we really sailed. And sailed fast. The boat was healing nicely over and everyone felt the excitement of a wonderful sail. We had a lot of sailors aboard and …

Beautiful sunset over the Annapolis City Skyline

August 8, 2012

Teachers, Clouds, Buy Boats & More

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Our first cruise of the day, 11:00 sail, we had a light breeze from the North that allowed us to sail at around 5 knots of boat speed, out into the middle of the Bay, into the shipping channel and back. We saw a bunch of anchored ships. One named “Genius” (funny name for a …

Sailing up the Severn River on the sunset sail as its raining

August 5, 2012


Captain's Blog1 Comment

What a day!  Amazing wind for the middle of summer. You have to love the days, as a captain, when you need to warn people where the “splash zone” is. On the first sail, we had 20-25 knot winds and sailed under the bridge in what felt like record time. On the way back to …

August 2, 2012

Intimate Details

2012 Photo Contest1 Comment

Enjoying everything local dinner cruise to celebrate our 9th wedding anniversary. This is how we ended our evening. What a view! Photo by Stephanie Sutton of Eldersburg, Maryland

August 2, 2012

Moonlight and Romance

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After a lovely evening with my wife celebrating our 9 years of marriage on the Everything Local dinner cruise , we sailed into Annapolis to this lovely view. Photo by Kevin Sutton of Eldersburg, Maryland

Woodwind sailing under the Chesapeake Bay Bridge while a car carrier crosses under too!

July 30, 2012

Room at the Bay Bridge

Captain's Blog1 Comment

Our first sail was with 11 people. The wind was beautiful and the clouds reminded me of the Caribbean. We sailed out with great wind for the first half of the trip and then the wind dropped down just as we headed into the Severn. One of the comment cards read, “Amazing trip… I want …

Sailing aboard the Woodwind II for a dinner cruise

July 29, 2012

takin a day off so dad can sail

Captain's Blog1 Comment

Captain Ken wanted to sail so Jennifer got to enjoy time with the passengers. Photo by dave pierce of centreville, va This photo was entered into our photo contest, but I think it deserves it’s own blog. (I published 2 of his photo contest entries already.) Dave and his wife came from Virginia to go …

Great photo as Woodwind II passes us at sunset in Annapolis

July 28, 2012

Best Sunsets lately!

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Our first sail was a private charter for a pretty full boat. The partners of the company were taking out their summer interns to say thank you. The bottles of bubbly were a favorite amongst the crowd. We had some very interested folks who loved sailing the boat and talking with me about navigation. We …

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