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
Racing into Annapolis Harbor

June 20, 2013

Perfect night on the Woodwind

Captain's Blog1 Comment

  We had just one sail today on the Woodwind, the other boat had all four cruises, but we only had one. Tonight was a private event, I call it a shmooze cruise. Well the weather and breeze could not have been any better for saying thank you to your best customers. We put up …
Read More >>

Another beautiful sunset from the Woodwind.

June 19, 2013

It’s Not Always about Going Fast and Racing…

Captain's Blog    No Comments

We had a very light wind day today on the Woodwind. And we had a 4.5 hour private event for employees and their families of a nearby engineering firm. They brought a bunch of kids that were very inquisitive. We did our very best to keep them happy and into the sailing even though we …
Read More >>

Beautiful sunset on USNA

June 17, 2013

Monday Funday!

Captain's Blog    No Comments

We had such a nice, small cruise on the 11:00 sail on Monday. Our crew member Frank wanted to show the kids aboard how to navigate by using a chart. Hayden, was very intrigued by the entire process. Frank showed him how to triangulate a position using lines of position and how to use a …
Read More >>

Sailing fast on the Woodwind

June 16, 2013

Happy Fathers on Father’s Day

Captain's Blog    No Comments

Working on Father’s Day is one of the best days to work on the Schooner Woodwind. You get happy families wanting to share sailing with their children.  Today was no different and we had wonderful weather. It was hot on land, but on the water we had a nice breeze. The breeze was so nice …
Read More >>

Crab eating at Cantlers, sailed over by the Woodwind

June 12, 2013

Crabs and Sailboat Racing… that’s what Annapolis does

Captain's Blog    No Comments

The wind was blowing and we were psyched to have a private charter book the boat for 5 hours to go to Cantler’s Crab House.  This would be my first trip to Cantler’s this season by Woodwind, which is always the best way to arrive at Cantler’s. Our cruise had 30 guests aboard and the …
Read More >>

Three friends celebrating a birthday on the Schooner Woodwind!

June 9, 2013

A little wind, a lot of fun

Captain's Blog    No Comments

Today was one of those days, when the wind didn’t really want to say hello to the Schooner Woodwind. We had a great team building program with multi girl scout programs within the MD/VA/DC region. The girls had a lot of fun enjoying their time aboard a 74-foot Schooner!  We had them sailing the boat, …
Read More >>

Minddrive Kids from Kansas City

June 8, 2013

Teamwork is Everything

Captain's Blog    No Comments

Everyone talks about team work, but really what is it? That was our challenge today with our JUNIOR Girl Scouts from Vienna, VA. So imagine, 26 girls that ranged from 9-11 years old. They all signed up for the “Power of Team” Sailing Cruise. This is where the crew and captain train the girls to …
Read More >>

Woodwind rounds the windward mark first.

May 29, 2013

It Ain’t Over Until…

Captain's Blog    No Comments

I only worked one sail today, the Wednesday Night Race.  Wow!  It was so much cooler on the Bay! During the race we saw 8-15 knots of wind. We picked a perfect racecourse that ended with enough time for the guests to take a turn at the helm. We had a bunch of young kids …
Read More >>

Sailing fast on Sunset Sail

May 25, 2013

One Sail, Two Sail, Three Sail, Four

Captain's Blog1 Comment

Winds were “honking” when I woke up. It’s going to be a terrific day for sailing, I thought. I even wrote this on Woodwind’s Facebook page while trying to find a pic of the Woodwind healing nicely to add to the post. When I arrived to the dock, the tide was down 2 feet from …
Read More >>

Getting ready for the start of the Wednesday Night Race. On the starting line just before the start.

May 22, 2013

Over 55 miles in one day

Captain's Blog    No Comments

What a day!  The wind started blowing from the SE at 10-15 and increased to over 22 knots by the 4:00 sail. We were lucky enough to have a 4.5 hour private charter for a day outing on the bay. We put just under 40 miles on the boat in just this cruise. We sailed …
Read More >>

© Copyright 2014. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.