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
Tony Lucca singing on the Schooner Woodwind

May 11, 2013

Tony Lucca sings and sails- May 10 & 11

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It has been over two and a half years that we have had Tony Lucca sing and perform on the Schooner Woodwind. A lot has happened since then, like he became the finalist on “The Voice” representing team Adam.  He also has a new CD coming out in June or July. Then he will get …

Schooner Woodwind Sailing Season starts

April 22, 2013

Sailing into 2013

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We have been waiting for the first sail of the season for 6 months! Sunday was not a day to disappoint! The wind was blowing from 10-18 knots and the sky was cloudless and bright blue. Today was a special day, we had the West Hill High School Choral Group on board. This choral group …

From atop the mainmast of Woodwind II at the Boat Show

October 8, 2012

Boat Show Wrap “Up”

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“Up” was the key word word of the day. At the start of the day we had a small issue with our lazy-jack system on the mast. So my day started with a ride up the foremast. Found a snarled and broken block, made a temporary repair and came back down the mast. But of …

Fred and Jody Krazeise at the helm of Woodwind

October 7, 2012

Cold Weather Sailing

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It was a cold, drizzly day by the 9 am. As we got the boat ready, we hoped for wonderful people that had a sense of adventure and enthusiasm. Our first cruise was a 25th Anniversary celebration! Fred and Jody Krazeise were the couple, and they made a weekend of the anniversary for their friends. …

US Sailboat Show in Annapolis obstructs the city skyline!

October 4, 2012

Show Boating at Boat Show

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The annual US Sailboat Show is here. The town is transformed, the skyline obstructed by sailboat masts, and everyone talks about sailing. This is one of my favorite times of year! We sail from the sailboat show on dock E2 on an hour and a half sail up to four times daily. In between sails, …

Golden glow of the sun as we sailed out of the Severn River.

September 30, 2012

Sunday Funday

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Today is the last day at the Annapolis Marriott until October 17, since the US Sailboat Show set-up starts later this evening. The Sailboat Show runs from October 4-8, click here for more info on how to sail with us then. Today was a stunningly beautiful day. We had great winds, although very flukey for …

1888 Sailing Vessel "Elf" sailing with all of her sails up

September 23, 2012

Girl Scouts sailing with Wooden Sailing Yachts

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Our first cruise was a Junior Girl Scout Program where we teach the girls how to sail the boat and work as a team on the Schooner Woodwind. The first lesson for them to learn was how to communicate. Picture all the girls learning the commands and nautical terms for sailing. We had them split …

Donnybrook (80+ foot race boat) sailing through the fleet of Hospice Cup

September 22, 2012

Hospice Cup Racing

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Today we had a fun-packed schedule of sailing cruises. And it was so nice that the wind wanted to contribute to the day! Our first cruise, we were asked to be a spectator boat for the Hospice Cup. A regatta to fund raise for 3 different Hospice programs in the area. We had the Montgomery …

Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

September 20, 2012

Amazing Sunset

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Today we had 2 sails on Woodwind II. A crew match race with the other Woodwind and a sunset shmooze cruise with dinner. For the Crew Match Race, a client privately charters both boats and we have the guests help us to win the race. We will have them switch their weight, tack the fisherman …

Sailing with lots of wind under the US Naval Academy Bridge

September 18, 2012

Wild & Windy

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The forecasts for today was a small craft advisory in the morning, then a gale warning for the afternoon, and then strong storms near 5:00. We had a 12:30-5:00 team building program where the clients learn how to sail the schooner and then race against their other team. With these wind conditions, Mike (the other …

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