Archive | Captain’s Blog

Sailing Woodwind Alongside a Trimaran at the Mouth of the Severn River

The problem with a fast boat…

  Everyone want to race ya We had some fun with this trimaran, while heading into the Severn River this evening.

Schooner Woodwind on the Bay

More Wind Please….

I think almost every time you mention the word Regatta the winds head the other way. At least that is what I am blaming the lack of wind on. Thisweekend is the Annapolis Race Week Regatta and I feel for all those people out there drifting around with out any wind. Hope fully today will […]

chesapeake sailing Woodwind Marriott

Lower the Main Sail

The wind was light, but pleasant.  We have sailed into the harbor.  Reluctantly, I turn on the engine and head Woodwind into the dying breeze and order the main lowered.  Andy, our crew member is able to get two young sailors to help lower the sail by pulling in our reef lines.  I call to […]

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 […]

Fran and Joe on Schooner Woodwind

Close Encounters of the Crew Kind…

So there I was on a beautiful Tuesday morning raising the sails when all of the sudden I was inundated with crew from all directions and in all types of water craft. Capt. Jen on the paddle board, Whitney on the laser, Sam in the blue kayak and Jocyln in the red kayak. What a […]

Adventure Saturday….

And that is exactly how the  day was. It was an adventure all day long. And everyone that came out with us today had the true adventurer spirit. Despite the rain, which wasn’t to bad, the wind was awesome and made the sailing exhilarating. With winds exceeding 20+ knots sometimes the boat was flying. We […]

J-Boats racing in very, very light air taken from our sunset sail on the Schooner Woodwind

Chillaxing on a Light Day

Today, we had a private charter book us for a 3 hour cruise. No… not the Gilligan’s theme song.  They were 5 minutes late, so no need to sing. Anyway, they all were teachers in a private school and wanted to relax before the first day of school on Monday. Relax they did. With very […]

Lesson #1 on Schooner Woodwind

New Sailors / Old Friends

Claudette from Phoenix is our newest sailing junkie. After dropping her daughter off to school and having some free time on her hands she came out sailing with us today. Letting us know that she wanted to take sailing lessons we put her in charge of the boat right away. After Rena explained the number […]

© Copyright 2015. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

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