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

“Do not go gentle into that good night.”

Storm clouds gathering over the schooner

This afternoon, aboard Woodwind II, we sailed with a crew of fun folks from a DC PR firm.  They held a fashion show and a talent contest aboard.  Our crewmate handsome Matt, fresh off the runways of Milan, warmed up the action.  He strutted down the Annapolis Waterfront Hotel Dock catwalk, donning the latest in … Read more

The Odd Couple

Two people rowing a wooden row boat with dog in it too

This weekend marks the start of Commissioning Week in Annapolis.  There are many activities and events surrounding the graduation of Midshipmen at the Naval Academy.  One of these events is the Class of 2015’s Ring Dance.  We were pleased to have Lindsey aboard today, a member of the class of 2015.  Lindsey received her ring … Read more

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

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

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


Schooner Woodwind departing Back Creek

  Charlotte, Don, and I started the day by inspecting Woodwind II’s mainmast.  We frequently perform inspections as a matter of maintenance to preserve the safety, performance, and aesthetic of our schooners.  While gathering tools and materials for the inspection, we saw Woodwind sailing into Back Creek, where we were docked.  I grabbed the boat’s camera, went … Read more

Short tacking Ego Alley

Two guests with fun hair dos that look like the wind is blowing their hair high into the air

  Our boats live at the mouth of Ego Alley, one of the busier intersections in town.  We see it all go down: cruisers making a dinghy run for ice cream cones, fishermen triumphantly returning for cold beers, backflips off of moored boats, stand up paddling with a dog, runabouts styling and profiling in their summer mating … Read more


Two very young guests helping to steer the schooner

    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!

Schooner Woodwind