Author Archive | Captain Jennifer

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

Hospice Cup Racing

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

Amazing Sunset

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

Wild & Windy

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 […]

Small Craft Warning aboard the Schooner Woodwind

Small Craft Advisory?

The only sail that we had today was a private event for the Heavy Seas Brewery! It was a sunset sail with full dinner and dessert. Sounds perfect… add in a Small Craft Advisory into the weather, and this makes it even more fun. As Hugh (owner of brewery) boarded the Woodwind, we joked how […]

Schooner Woodwind and Martha White meet in Annapolis

It’s Schooner Season

I hope this fall sailing pattern is setting in. We have had some  glorious sailing days in the past 5 days. Today was no different, we had winds just topping 10 knots and beautiful blue, crisp skies. The first trip filled up quick for a mid-week lunch-time cruise. A local association treated their employees to […]

Wedding aboard the Schooner Woodwind II

Wedding, Winds & Wetness

What a day! The day started out with the wedding of Stephanie Mafrici and Frank Cook. This couple sailed with me earlier in the season to see about having their wedding aboard. By the time we got back to shore the wedding was planned.   They wanted the ceremony to be on the Woodwind, while […]

Sailing into the Sunset with local music aboard the Woodwind

Singing & Sailing into the Sunset

Woke up to the sound of rain. So much rain, that no one signed up for the first sail today.  By the second sail, 3:00-5:00, we had 2 lovely people sign up. They had a private cruise (for $72)!  We had perfect wind and made it under the Bay Bridge and back. Maureen and Jim […]

Sailing around the submarine off of Annapolis

Circumnavigating a Submarine

The first day of Labor Day Weekend has begun. We had about 25 people on our early sail and we had about 10-14 knots of breeze. Within a half hour of the sail, we spot a submarine in the distance. We just had to check it out.  I decided to circumnavigate the sub, while staying […]

"The Roadside Show" performs on the Schooner Woodwind

Breeze + Music= Great

We had some great breezes today. It’s funny how “great breeze” might be defined among the captains and crew on the Woodwinds. To us, the crew of the Woodwind II, for today… we had great breezes. Why? The forecast was for no breeze. While we were getting the boat ready to sail, we had no […]

Sailing the Schooner Woodwind into the Chesapeake

Fish, Sail, Fish

The day started by a warm greeting on the dock by Steve. He admired the Woodwind for many years and was excited to finally make today the day he was going to sail on her.  He was out fishing earlier on his boat and he said it was blowing around 18 knots. He shared that […]

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