Archive | Captain’s Blog

Flying Dog's new Atlantic Lager

Dogtoberfest….And Flying Dogs

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 […]

Lauren at the wheel of Schooner Woodwind

History Mondays are History….

  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 […]

1888 Sailing Vessel "Elf" sailing with all of her sails up

Girl Scouts sailing with Wooden Sailing Yachts

Our first cruise was a Junior Girl Scout Program where we teach the girls how to sail the boat and work as a team on the Schooner Woodwind. The first lesson for them to learn was how to communicate. Picture all the girls learning the commands and nautical terms for sailing. We had them split […]

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 […]

Connie sailing and celebrating

Fun Day on the Water….

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 […]

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 Cruises, Chesapeake Bay, Annapolis Marriott Waterfront Hotel, schooner

Music on the water (two Woodwinds, mandolin, violin, guitar and voice)

Woodwind was aptly named.  Made of wood and driven by the wind.  The musical side of the name is also inescapable.  Clarinet, oboe, bassoon, to name a few.  Guitar, mandolin, and violin may not be the wind part, but they are wood.  Add voice and you add wind.  So tonight, Thursday, we have those very […]

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 […]

William as John Sands on History Monday

History Mondays are Winding down

  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. […]

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