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Schooner Woodwind Sailing Cruises

Outdoor Venue

80 Compromise St, Annapolis, MD 21402

Event Types

food_drink (67)sports (14)other (4)family (2)workshop (2)music (1)
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Upcoming Events (25)

History Monday
Mon, Aug 3, 20266:30 PM
History of Greenbury Point
Mon, Aug 3, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Sue has been researching Annapolis history for the last 6+ years and is writing a book on the Historic Himes of Annapolis. Sue also co- founded Save Greenbury Point.[/vc_column_text][vc_custom_heading text=”Details” use_theme_fonts=”yes”][vc_column_text css=””] History Monday Sunset Sails occur every Monday, May-Se

Beer Tasting Sunset Sail
Tue, Aug 4, 20266:30 PM
Wednesday Night Racing
Wed, Aug 5, 20266:30 PM
History Monday
Mon, Aug 10, 20266:30 PM
Lighthouses on the Chesapeake Bay
Mon, Aug 10, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]John Potvin retired in 2015 and started volunteering at the Thomas Point Shoal Lighthouse. He was appointed the Lighthouse Manager in 2020 and has been instrumental in the restoration of the lighthouse. He is a Certified Chesapeake Bay Storyteller and lives in Annapolis within site of the historic lighthouse.[/vc_column_text][vc_custom_heading text=”Details

Beer Tasting Sunset Sail
Tue, Aug 11, 20266:30 PM
Wednesday Night Racing
Wed, Aug 12, 20266:30 PM
History Monday
Mon, Aug 17, 20266:30 PM
Greenbury Point – Towers to the Past
Mon, Aug 17, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Steve Carr attended the U.S. Naval Academy and rode his bicycle twice across the United States. He worked for fifteen years at the Grand Canyon, ran a successful political and environmental consulting company, and was in charge of state trails for the Maryland Department of Natural Resources before retiring. Steve has been a competitive sailor and covered yachtin

Beer Tasting Sunset Sail
Tue, Aug 18, 20266:30 PM
Wednesday Night Racing
Wed, Aug 19, 20266:30 PM
History Monday
Mon, Aug 24, 20265:30 PM
Legends & Lore of the Annapolis Waterfront
Mon, Aug 24, 20265:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Author and historian David Gendell is a lifelong Annapolis sailor and frequent speaker aboard the Woodwinds. He is the co-founder of SPINSHEET, the Chesapeake Bay sailing magazine.[/vc_column_text][vc_custom_heading text=”Details” use_theme_fonts=”yes”][vc_column_text css=””] History Monday Sunset Sails occur every

Beer Tasting Sunset Sail
Tue, Aug 25, 20265:30 PM
Wednesday Night Racing
Wed, Aug 26, 20265:30 PM
History Monday
Mon, Aug 31, 20265:30 PM
America 250 – Annapolis and the Birth of the Republic
Mon, Aug 31, 20265:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Michael Bors is an Annapolis native, history enthusiast, and experienced sailor. He recently completed his PhD in philosophy at the Catholic University of America. He also offers walking and boat tours through TourAnnapolis.com, a business he founded to share the beauty of Annapolis with the world. He looks forward to recounting Annapolis’s fascinating Revo

Beer Tasting Sunset Sail
Tue, Sep 1, 20265:30 PM
History Monday
Mon, Sep 7, 20265:30 PM
The Animal that Built America – The Eastern Oyster
Mon, Sep 7, 20265:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Jesse Iliff is executive director of the Severn River Association. He grew up on the Severn River and knew early on he wanted to do whatever he could to protect and restore the river and the bay. A lawyer by training, Jesse began his career in conservation as a riverkeeper and became a scientist by experience. Now he combines his experience and training to advoca

Beer Tasting Sunset Sail
Tue, Sep 8, 20265:30 PM
History Monday
Mon, Sep 14, 20265:30 PM
Chesapeake Patriots: Celebrating America at 250 by Uplifting the Voice of African Americans in the Fight for Democracy
Mon, Sep 14, 20265:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Dee Strum CEO, Blacks of the Chesapeake, and a frequent presenter to students and adults on the region’s Black History and environmental justice. Greg Gwaltney is a retired environmental scientist and 5th-generation Black Waterman family descendent with family members who continue to work as watermen on the Potomac and James Rivers.[/vc_column_text][vc_cust

Beer Tasting Sunset Sail
Tue, Sep 15, 20265:30 PM

Recent Past Events at Schooner Woodwind Sailing Cruises

Wednesday Night RacingWed, Jul 29, 2026
Beer Tasting Sunset SailTue, Jul 28, 2026
History of Watermen on the ChesapeakeMon, Jul 27, 2026
History MondayMon, Jul 27, 2026
Wednesday Night RacingWed, Jul 22, 2026
Beer Tasting Sunset SailTue, Jul 21, 2026
History of Greenbury PointMon, Jul 20, 2026
History MondayMon, Jul 20, 2026
Wednesday Night RacingWed, Jul 15, 2026
Beer Tasting Sunset SailTue, Jul 14, 2026
Lighthouses on the Chesapeake BayMon, Jul 13, 2026
History MondayMon, Jul 13, 2026
Wednesday Night RacingWed, Jul 8, 2026
Beer Tasting Sunset SailTue, Jul 7, 2026
History MondayMon, Jul 6, 2026

Artists Who Have Performed at Schooner Woodwind Sailing Cruises

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