Author Archive | Captain Jennifer

Sailing into the sunset on the Chesapeake Bay

Hot Summer Breeze

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 […]

Chris and Kristin surprise proposal aboard Woodwind

“At least she said yes…”

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. […]

The Roadside Show Band playing on the Schooner Woodwind II

Foot Stompin’ Music

What a hot day!!  The breezes were playing peek-a-boo with us. We had a delightful sail on our 11:00 sail with a cool breeze from the Bay. On the 2nd and 3rd cruise, the breeze was less consistent, but we found a way to keep cool with the 5th sail aboard. The D-Sail (diesel). By […]

Moon rising above anchored fleet for Annapolis fireworks

Independence Day

We started the sail with virtually no wind, so I decided to motor to Thomas Point Lighthouse. As we get close, the wind picked up and were able to sail back to Annapolis. We anchored with great visibility of the fireworks and of the city skyline.  All I kept thinking of was how lucky I […]

Sailing into the sunset on Woodwind

A Hot Breezy Day

It was a scorcher… on land. Out on the water we had a nice breeze for 3 of the 4 sails. The first sail was the battle of the land breeze with the sea breeze. We had good breeze, until we sailed in the convergence zone where there was none. This is always fascinating to […]

Scaffolding work being done on the Chesapeake Bay Bridge

Men at Work

We had a busy day with private charters. We had a company do a shmooze cruise with clients that they wanted to say thanks for all the business that they give them. I like the word shmooze cruise. They chartered the boat for 4 1/2 hours, and we got to Thomas Point Light, under the […]

Wednesday Night Racing on the Schooner Woodwind

Windy, Windy Day

What a terrific day we had on the water today!! The  first sail we had a girl scout cruise along with some other public guests. They were treated to some fantastic sailing. We started with all 4 sails, and had to lower the fisherman before we tacked as we made it under the Bay Bridge. […]

Hiking out on the Woodwind with J-World Sailing Instructors

Sailing School takes over Woodwind

Tonight, we sailed with one of my favorite groups of the season… J-Word Sailing School. All season, we sail around each other telling our guests about their sailing school and what maneuver they are teaching their students at that moment. It may be a man overboard drill, how to hove-to, or just how to sail […]

Sailing with the Roaming Gnome

There’s no place like gnome

A beautiful Saturday filled with wind seemed like a fairy tale. But that is what we had for the 11:00 sail! We sailed straight across the Chesapeake Bay. Cool breezes with low humidity was a wonderful way to start the day! The low humidity was with us all day. The breezes slowed down as the […]

Cleaning up the Bay

It was a strange day on the water. All sails except the first sail had virtually no breeze for a part of the cruise. And then all within the same cruise, the wind picked up and we were going 7.5 knots and the boat is healed over. Most of this was due to small clouds […]

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