2024 Sailing Season is coming! See you April 13, 2024!

Out in the Breeze

Naval Academy Sunset from Schooner Woodwind

We had 4 great sails today, and being out on the bay was the place to be today. With the heat inshore it paid to be out in the breeze and sailing. We had breeze on all our sails except the last 30 minutes of our 4:00 sail. We had a lot of fun groups … Read more

South By Southwest….

We had a great day for sailing today and had a nice south west breeze. This enabled us to get close to the Thomas Point Lighthouse on one of our cruises today. You can definitely tell summer is here though on the water. It is nice when that sea breeze finally fills in from the … Read more

Men at Work

Scaffolding work being done on the Chesapeake Bay Bridge

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 … Read more

Windy, Windy Day

Wednesday Night Racing on the Schooner Woodwind

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. … Read more

Let’s Go Sailing

Drawing from a guest on the Schooner Woodwind

Today’s blog was inspired by this great couple that came out sailing today. They had just been out with us last week and purchased a couple of our spectacular Woodwind Koozies (free beer every time you  you come back). So in the morning they looked over and saw the koozies and said ” Let’s  go … Read more

Sailing School takes over Woodwind

Hanging out on the Woodwind with J-World Sailing Instructors

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 … Read more

Windy Monday

Boy did we ever have winds. Every sail we did today we started with a certain amount of sails up and ended up taking some down as the wind strength picked up all day. Our first charter was a team building exercise and we ended up having to drop the Fisherman sail and finish the … Read more

Boat Designs

Moth Sailboat flying/sailing through the water

The NE breeze took Woodwind II to Thomas Point Lighthouse today.   Along the way we came across some amazing small boats, a Moth and a gaff rigged schooner.  There’s a boat out there for everyone, different styles serving different purposes!

There’s no place like gnome

Captain Jen sailing with the Roaming 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 … Read more

Beautiful Sunset

Sunset off of Woodwind's stern.

We had a great day sailing Thursday and beat the heat by staying on the water all day. The breezes were light but we were able to avoid using the dreaded 5th sail, the D-Sail (our trusty diesel). Our 1st and 3rd sails had about 20 people apiece, our 2nd sail had one couple from … Read more

Schooner Woodwind
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