Archive | Captain’s Blog

Matt on the Helm

Relaxing on the Water……

What a great day of sailing we had Saturday. The Perron family was back to sail with us again and it was good to see you guys. Matt and Becca both took turns at the wheel and they did great. The winds were light, but it was not hot out and it made for a […]

Crab eating at Cantlers, sailed over by the Woodwind

Crabs and Sailboat Racing… that’s what Annapolis does

The wind was blowing and we were psyched to have a private charter book the boat for 5 hours to go to Cantler’s Crab House.  This would be my first trip to Cantler’s this season by Woodwind, which is always the best way to arrive at Cantler’s. Our cruise had 30 guests aboard and the […]

Three friends celebrating a birthday on the Schooner Woodwind!

A little wind, a lot of fun

Today was one of those days, when the wind didn’t really want to say hello to the Schooner Woodwind. We had a great team building program with multi girl scout programs within the MD/VA/DC region. The girls had a lot of fun enjoying their time aboard a 74-foot Schooner!  We had them sailing the boat, […]

Minddrive Kids from Kansas City

Teamwork is Everything

Everyone talks about team work, but really what is it? That was our challenge today with our JUNIOR Girl Scouts from Vienna, VA. So imagine, 26 girls that ranged from 9-11 years old. They all signed up for the “Power of Team” Sailing Cruise. This is where the crew and captain train the girls to […]

Happy Birthday!


    This morning, Annapolis was graced with excellent southerly winds arriving ahead of the cold front!  We celebrated the birthday’s of cousins Ethan and Paxton.  Ethan is now 4 and Paxton is 1 year old. Check out their cool birthday shirts!

Young Keegan takes command.

Sunday Cruises and what really BIG is!

The wind blew from the South West today.  It was an easy beam reach as we headed out across the bay.  The Kermizian, Hadfield and Renda families introduced themselves to me in the cockpit for our 1:30 cruise.  Many of them came from New Jersey on a family outing.  They were a delight to have […]

Woodwind II crosses Woodwinds bow, only so I could get the picture(haha)

Is there anyone out there celebrating???

THERE ARE!! And they all found their way to the boat yesterday. All day long we had people aboard celebrating anniversaries, birthdays, bachelorette parties and just plain getting away from it all to go sailing. And the day could not have been any better. The sun was out and it was nice and warm and as […]

Woodwind rounds the windward mark first.

It Ain’t Over Until…

I only worked one sail today, the Wednesday Night Race.  Wow!  It was so much cooler on the Bay! During the race we saw 8-15 knots of wind. We picked a perfect racecourse that ended with enough time for the guests to take a turn at the helm. We had a bunch of young kids […]

Osprey sitting out on Back Creek

Cruising for chicks!

Coming off a busy Memorial Day weekend, my crew-mates Don, Kevin, and I welcomed today’s lighter breeze on Woodwind.  After leaving the harbor with some guests, we decided to head around the Eastport peninsula to check on some of the osprey.  We cruised past George and Martha, the ospreys that reside on the Horn Point shoal marker. […]

As the sunsets behind Schooner Woodwind another Monday is History

Monday is History….

Another great day of sailing on the Chesapeake Bay is History. Every Monday we have a guest visitor from Historic Annapolis that joins us for our sunset sail. Thank you to Author/photographer Roger Miller who joined us this week.Roger spoke about several historical sights in Annapolis that should be a must see for everyone while […]

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