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

Happy Fathers on Father’s Day

Sailing fast on the Woodwind and guests holding on

Working on Father’s Day is one of the best days to work on the Schooner Woodwind. You get happy families wanting to share sailing with their children.  Today was no different and we had wonderful weather. It was hot on land, but on the water we had a nice breeze. The breeze was so nice … Read more

Crabs and Sailboat Racing… that’s what Annapolis does

Guest eating crabs at Cantlers, sailed over by the Woodwind

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 … Read more

A little wind, a lot of fun

Three friends celebrating a birthday on the Schooner Woodwind!

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, … Read more

Teamwork is Everything

Minddrive Kids from Kansas City

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 … Read more

It Ain’t Over Until…

Woodwind rounds the windward mark first.

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 … Read more

One Sail, Two Sail, Three Sail, Four

Sailing fast on Sunset Sail

Winds were “honking” when I woke up. It’s going to be a terrific day for sailing, I thought. I even wrote this on Woodwind’s Facebook page while trying to find a pic of the Woodwind healing nicely to add to the post. When I arrived to the dock, the tide was down 2 feet from … Read more

Over 55 miles in one day

Getting ready for the start of the Wednesday Night Race. On the starting line just before the start.

What a day!  The wind started blowing from the SE at 10-15 and increased to over 22 knots by the 4:00 sail. We were lucky enough to have a 4.5 hour private charter for a day outing on the bay. We put just under 40 miles on the boat in just this cruise. We sailed … Read more

Lighthouse Cruise on the Bay

Thomas Point Lighthouse

The cruise we had today was the re-named Blue Angels Cruise.  After the Blue Angels were canceled due to sequestration, we had many people signed up for this cruise. We changed the theme to a Lighthouse Cruise and asked them what they wanted to do, and many wanted to stay on the cruise. So, we … Read more

Remembering what makes Annapolis special

Sunset on the Annapolis Skyline

You’ve heard people say, “I never explore what’s in my own backyard”. Tonight, we took out many local, downtown businesses through the Annapolis Business Association and Bricks and Clicks organization for them to explore their own backyard. We had about 30 people join us for a two hour sunset sail to the Bay Bridge and … Read more

Happy Mother’s Day!!

Going through the buffet line on the Schooner Woodwind II for Mother's Day Brunch.

What a terrific Mother’s Day. The wind was howling and the sky was absolutely clear. Terrific day for sailing! Having Mother’s Day Brunch? Maybe the conditions were not ideal due to the high winds, but all of the guests had a terrific time and raved about the food. The salmon and beef were amazing, were … Read more

Schooner Woodwind
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