Bootlegger

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Bootlegger The sailing adventures of weekend Pirates of the Chesapeake Sean, Laurie and Sammi are excited to begin our new adventures on Bootlegger.

Through this page, you can stay in touch with us and follow us as we travel around the Chesapeake Bay.

Late to post, but we had a great time catching up with friends and checking out boats at the Us Sailboat Show- Annapolis...
10/23/2026

Late to post, but we had a great time catching up with friends and checking out boats at the Us Sailboat Show- Annapolis Md last weekend.

Quick trip to Pirates Cove for the crew of Bootlegger.
09/20/2026

Quick trip to Pirates Cove for the crew of Bootlegger.

09/10/2026

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More w**e. Dinner with our Hunter Sailing Association Station #1 friends and the Reagan Years at the Jetty. Another ...
09/07/2026

More w**e. Dinner with our Hunter Sailing Association Station #1 friends and the Reagan Years at the Jetty. Another great day on Bootlegger!

Hunter Sailing Association Station #1 w**e cruise!
09/06/2026

Hunter Sailing Association Station #1 w**e cruise!

09/05/2026
08/31/2026
08/17/2026

So much fun!

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Herrington Harbour North
Tracys Landing, MD

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