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

The Start of a Race means everything

Racing schooners

It was an exciting start to the Wednesday Night race this week. We just finished our rules seminar with J World Sailing School, so we ready to practice using the rules. See all the photos on our Facebook page.

Pleasant Living

Sunset over the Statehouse

Living aboard is a lifestyle that is relatively common around the temperate mid-Atlantic coast.  In Annapolis, there are folks that weekend on boats, some stay for a season, some for a lifetime.  It’s a good place to be, the Land of Pleasant Living is what my favorite beer proclaims!  I always look forward to staying … Read more

May Day!

Couple cruising back to the Marriott Dock

Please don’t misunderstand, there was no emergency today.  May 1, commonly referred to as May Day, is the traditional spring holiday.  Sure, around Annapolis, the tradition of burning socks on the spring equinox is more popularly celebrated.  Still, May Day is a fine reason to grab a friend for a beer and a sail.   After … Read more

Cocktail Cruise up the Severn

Cocktail Cruise up the Severn

What do you do when the wind gusts up to 30 knots and you have food and cocktails to serve?  Not only that, but many of our guests are dressed up for an elegant cruise with a gentle breeze.  Thank goodness for the Severn River and the adaptable schooner rig.  “Folks, the sun is shining, … Read more

Annapolis Spring Sailboat Show Weekend

Making 10kts on Woodwind

This weekend is the Annapolis Spring Sailboat Show.  This event has been growing bigger every year, and attracts a variety of sailors.  It’s a great opportunity to pick up some fresh gear, shop for new rigging, buy the boat of your dreams, or just kick the tires.     Woodwind and Woodwind II are sailing out … Read more

Thumbs Up to Opening Weekend

First day of sailing on Woodwind

The day has finally arrived! The boat is shiny and beautiful, fresh out of winter maintenance work and it is time to actually sail! Even though, the first day of sailing was yesterday… it was my first day of sailing today. We had great winds around 15 knots and sailed almost to Thomas Point Lighthouse … Read more

Opening Day

Brennah and her sister win a print of Nancy Hammond's "Woodwind"

Baseball, rockish, and Chesapeake sailing season.  There’s always a sense of urgency, longing, anticipation, and burning for opening days.  Okay, maybe burning is going too far.  Regardless, Woodwind sailed twice today, and scratched the itch.  Woodwind II came out to play in the mid afternoon.                 To celebrate, we … Read more

This Must Be The Place

Don Avery, Crewmate Eternal

  Hooray!  Today, Woodwind landed in her slip at the Annapolis Waterfront Hotel Dock on Spa Creek!  All the while, I had the Talking Heads song “This Must Be the Place (Naive Melody)” running through my head 🙂  Securing lines at the mouth of Ego Alley gave me a sense of restoration and content.  The … Read more

Sweet Racing and Sunsets

Woodwind sails by just before the sun sets.

What a beautiful Saturday! When I saw how much wind was out there, I knew we could make it to see the J70 North American Championships being held in the middle of the Bay. This was my goal for the day. I wanted show guests a starting line with 90 boats on it, but had … Read more

Annapolis Classic Boat Regatta

Elf sailing, with everything flying

Annapolis is such a fun place to sail out of.  Today we were able to watch classic wooden boats race in the harbor.  This race was set up by Captain Rick Carrion.  Rick is the captain and owner of the oldest race boat in the USA.  Elf was built in 1888 and has been painstakingly … Read more

Schooner Woodwind
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