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

Dogtoberfest….And Flying Dogs

Flying Dog's new Atlantic Lager

Our last beer tasting of the season. Flying Dog Brewery is our sponsor this evening and we will be tasting 3 of their wonderful beers. Ben Wiser from the brewery will be Flying Dog’s representative aboard the Woodwind this evening. Always fun and entertaining it is a pleasure to have Ben aboard. And what a … Read more

History Mondays are History….

Lauren at the wheel of Schooner Woodwind

  We had 3 great sails today. The winds were a little fluky in the river in the morning but by the last 2 sails it had settled down to a steady direction from the north and the sailing was fantastic. We had fun people out all day. The group sizes are getting a little … Read more

Fun Day on the Water….

Connie sailing and celebrating

I think the weather has something to do with it, but everyone seems to have a spring in their step and just be in overall good mood. The day was awesome. We had great wind a fun crew and wonderful guests all day. Our 1st sail started out with several frequent sailors joining us for … Read more

History Mondays are Winding down

William as John Sands on History Monday

  Only one more History Monday to go for the season.  Tonight we had William from Historic Annapolis out with us and everyone thouroughly enjoyed his portrayal of John Sands. Thank you William. Besides William’s wonderful performance we also had wonderful sailing. The breezes were blowing between 12-15 knots and the boat was roaring along. … Read more

Saturday’s Sails….B&B Sunrise

Sunrise In Annapolis Aboard Schooner Woodwind

We had a great day of sailing today. The winds were steady in the 12 to 15 knot range and we had a 4.5 hour  charter. We sailed down to Thomas Point Light and then most of the way to Bloody Point Light then all the way back up the bay to home. What a … Read more

Saturday’s Sails….B&B Sunrise

Sunrise In Annapolis Aboard Schooner Woodwind

We had a great day of sailing today. The winds were steady in the 12 to 15 knot range and we had a 4.5 hour  charter. We sailed down to Thomas Point Light and then most of the way to Bloody Point Light then all the way back up the bay to home. What a … Read more

Another Great Day of Sailing…..

Jim and Michele at the Wheel of Schooner Woodwind

And the wind came up for the end of the week just great. We had 3 excellent sails today. On our 1st sail we had a couple that actually grew up with one of the brother s that owns the company in Albany,NY. where the Woodwinds were built. Michele and Jim had a great time … Read more

Can You Say Fall Sailing….WOW

Sunset Anniversary Sailabration

We had the most incredible day of sailing yesterday. Everyone who came out with us was treated to one of the better days of sailing we’ve had in a long time. The temperatures felt like a nice fall day. Cool, crisp and really clear. The visibility was fantastic up and down the bay all day. … Read more

More Wind Please….

Schooner Woodwind on the Bay

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 … Read more

Close Encounters of the Crew Kind…

Fran and Joe on Schooner Woodwind

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 … Read more

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