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
Great photo as Woodwind II passes us at sunset in Annapolis

July 28, 2012

Best Sunsets lately!

Captain's Blog    No Comments

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 …
Read More >>

Wednesday Night Racing on the Schooner Woodwind

July 25, 2012

Teamwork

Captain's Blog    No Comments

Today we had a 4 1/2 hour team-building cruise on the Bay. A company chartered us out to have their team have fun, but also work together. It was a nice small group of only 12 people, so after lunch, we started the training. It was very interesting to see how everyone got along and …
Read More >>

Wine in the Wind on Schooner Woodwind in Annapolis

July 22, 2012

Wine in the Wind

Captain's Blog2 Comments

What a terrific day! I love the wine tastings we do on the Schooner Woodwind! French Wines were the theme today, each “Wine in the Wind” has a different theme. Franck Agostino was the host today. And he knows wine. His job is the coolest job, I might add. He is from France and he …
Read More >>

Fun loving group from Cincinnati aboard the Schooner Woodwind II

July 21, 2012

Smiling in the Rain

Captain's Blog    No Comments

It was a rainy Saturday.  Everyone is calling, “are you still going sailing, even in the rain”? Yes, we sail rain or shine. Ponchos were handed out to everyone and the rustle of poncho plastic made each sail unique. We had wind, a nice breeze from the NE that had us doing about 8-9 knots. …
Read More >>

Woody, the grasshopper, goes for a ride on Schooner Woodwind

July 19, 2012

Friends and Mascots

Captain's Blog    No Comments

We always get the most wonderful people that sail on the Woodwinds! On our 11:00 sail, we only had 7 guests aboard. But they felt like friends immediately.  Dave was celebrating his birthday with his grandparents (almost 21st birthday) and he had a blast learning all about sailing. He was hooked into the love and …
Read More >>

July 18, 2012

Thank you Mother Nature

Captain's Blog    No Comments

Today was a very interesting day on the Woodwind. We had a team building for the first 2 cruises and then 2 public sails afterwards. One of those public cruises was the Wednesday Night Race. Thank you Mother Nature for 15 knots of wind from the SW! We had a good teambuilding with a company …
Read More >>

Sailing to Cantler's to enjoy a Maryland Crabfeast

July 17, 2012

Feeling Crabby

Captain's Blog    No Comments

We only had one sail today, a round trip private cruise to Cantler’s Crab House. This is my first cruise to Cantler’s on Woodwind this season so I was excited for it. The wind was blowing beautifully, 10 knots, from the NW as we gybed our way out of the Severn with about 35 guests. …
Read More >>

Amazing clouds building in the sky as we sailed around the Chesapeake all day

July 10, 2012

We needed the rain?

Captain's Blog    No Comments

As I walked down the dock this morning, schools of fish were everywhere. They were schooling in the most gorgeous way. This was so mesmerizing. It was a nice pleasant day on the water. Most of the boat traffic was from the 10 sailing camps on the Severn River. I may be exaggerating a little …
Read More >>

Sailing into the sunset on the Chesapeake Bay

July 8, 2012

Hot Summer Breeze

Captain's Blog    No Comments

All everyone was talking about was the heat… on Sunday, we were talking about the breeze. We had a nice breeze pick up from the NE. First cruise, we were able to sail around the US Junior Sailing Olympics. They had 3 different fleets out in the Chesapeake Bay. They had Lasers, 420′s and Optimist …
Read More >>

Chris and Kristin surprise proposal aboard Woodwind

July 6, 2012

“At least she said yes…”

Captain's Blog    No Comments

We were privately chartered for a special cruise tonight on our sunset sail. My cruise details said that we were having a surprise proposal happen. At 6:10, friends of Chris Wood and Kristen came to board the boat early for the surprise. They would be hiding below and come up when he pops the question. …
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.