Author Archive | Captain Mike

"Rage, rage against the dying of the light."

“Do not go gentle into that good night.”

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 […]

Float Everything!

The Odd Couple

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 […]

Sunset over the Statehouse

Pleasant Living

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 […]

Cruising back to the Marriott Dock

May Day!

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 […]

Making 10kts on Woodwind II

Annapolis Spring Sailboat Show Weekend

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 […]

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

Opening Day

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 […]

Don Avery, Crewmate Eternal

This Must Be The Place

  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 […]

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 […]


Short tacking Ego Alley

  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 […]

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!

© Copyright 2018. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.