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Schooner Woodwind Sailing Cruises

Outdoor Venue

80 Compromise St, Annapolis, MD 21402

Event Types

food_drink (60)sports (14)other (13)workshop (1)music (1)
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Upcoming Events (25)

Annapolis to Bermuda Ocean Race Watch Cruise
Fri, Jun 5, 202612:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Watch the start of the annual Annapolis to Bermuda Ocean Race aboard the 74-foot, Schooner Woodwind. The Annapolis to Bermuda Ocean Race — or A2B — started in 1979, and covers 753 miles, making it one of the longest ocean races on the east coast of the U.S. The challenging course combines inshore and offshore, down the Chesapeake Bay and across the Gulfstr

History of Watermen on the Chesapeake
Mon, Jun 8, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]James Ronayne is a sophomore at Cornell University, majoring in Environment and Sustainability with a focus on Environmental Law. He is an environmental photographer, conservationist, and storyteller. Ronayne’s photography is heavily influenced by the Chesapeake Bay and the watershed region. His photographs highlight the working men and women of the Bay and the e

History Monday
Mon, Jun 8, 20266:30 PM
Beer Tasting Sunset Sail
Tue, Jun 9, 20266:30 PM
Wednesday Night Racing
Wed, Jun 10, 20266:30 PM
Battle of the Severn
Mon, Jun 15, 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

History Monday
Mon, Jun 15, 20266:30 PM
Beer Tasting Sunset Sail
Tue, Jun 16, 20266:30 PM
Wednesday Night Racing
Wed, Jun 17, 20266:30 PM
Father’s Day Brunch Sail
Sun, Jun 21, 202611:00 AM111.42
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Sail Dad away! Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage.[/vc_column_text][vc_custom_heading text=”Details” use_theme_fonts=”yes”][vc_column_text css=””] We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Departi

History of Watermen on the Chesapeake
Mon, Jun 22, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]James Ronayne is a sophomore at Cornell University, majoring in Environment and Sustainability with a focus on Environmental Law. He is an environmental photographer, conservationist, and storyteller. Ronayne’s photography is heavily influenced by the Chesapeake Bay and the watershed region. His photographs highlight the working men and women of the Bay and the e

History Monday
Mon, Jun 22, 20266:30 PM
Beer Tasting Sunset Sail
Tue, Jun 23, 20266:30 PM
Wednesday Night Racing
Wed, Jun 24, 20266:30 PM
Skipjacks Living Symbols of the Chesapeake Bay
Mon, Jun 29, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Susan Schneider, raised in the historic seaport of Charleston, South Carolina, and formally trained in historic architecture, now volunteers in the maritime community, combining her passion for sailing with public education. She leads tours for several nonprofit organizations dedicated to preserving Maryland’s iconic skipjacks. In 2025, Susan spearheaded the retu

History Monday
Mon, Jun 29, 20266:30 PM
Beer Tasting Sunset Sail
Tue, Jun 30, 20266:30 PM
Fireworks Cruise
Sat, Jul 4, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail. We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show.[/vc_column_text][vc_custom_heading text=”Details” use_theme_fonts=”yes”][v

The Life & Times of Chesapeake Bound (1763–1765)
Mon, Jul 6, 20266:30 PM
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[vc_row gap=”35″][vc_column width=”1/2″][vc_column_text css=””]Thomas Guay is the author of Chesapeake Bound, a historical novel set in the uneasy years just before the American Revolution. Set between 1763 and 1765, the novel follows indentured servants on a perilous voyage to America, where storms, sickness, betrayal, and even Barbary corsairs test their hopes for a better life—only to find themselves on the brink of revol

History Monday
Mon, Jul 6, 20266:30 PM
Beer Tasting Sunset Sail
Tue, Jul 7, 20266:30 PM
Wednesday Night Racing
Wed, Jul 8, 20266:30 PM
Lighthouses on the Chesapeake Bay
Mon, Jul 13, 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

History Monday
Mon, Jul 13, 20266:30 PM
Beer Tasting Sunset Sail
Tue, Jul 14, 20266:30 PM

Recent Past Events at Schooner Woodwind Sailing Cruises

Wednesday Night RacingWed, Jun 3, 2026
Beer Tasting Sunset SailTue, Jun 2, 2026
History MondayMon, Jun 1, 2026
The Life & Times of Chesapeake Bound (1763–1765)Mon, Jun 1, 2026
Wednesday Night RacingWed, May 27, 2026
Beer Tasting Sunset SailTue, May 26, 2026
America 250 – Annapolis and the Birth of the RepublicMon, May 25, 2026
History MondayMon, May 25, 2026
Acoustic Brunch Sail with Gareth AsherMon, May 25, 2026
Blue Angels Performance CruiseWed, May 20, 2026
Wednesday Night RacingWed, May 20, 2026
Beer Tasting Sunset SailTue, May 19, 2026
America 250 – Annapolis and the Birth of the RepublicMon, May 18, 2026
History of Greenbury PointMon, May 18, 2026
History MondayMon, May 18, 2026

Artists Who Have Performed at Schooner Woodwind Sailing Cruises

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