Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind.
We feature a History-slanted sunset sail every Monday night (May through September). When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries. We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town. Topics change weekly.
We are working on the 2019 calendar now and will post it soon
Schedule for History Mondays 2018:
Monday, May 14: The Key to Annapolis History, Jeff Holland 6:30-8:30
The key to Annapolis history lies somewhere in the harbor… Jeff uses his original songs and narrative verse to tell three centuries worth of stories about Annapolis, some of which are actually true.
Monday, May 21: The Key to Annapolis History, Jeff Holland 6:30-8:30
The key to Annapolis history lies somewhere in the harbor… Jeff uses his original songs and narrative verse to tell three centuries worth of stories about Annapolis, some of which are actually true.
Monday, May 28: Tunes & Tales of the Golden Age of Annapolis, Tom Guay 6:30-8:30
On Schooner Woodwind’s History Monday cruises, Tom’s fiddle playing takes you on a trip back in time to The Golden Age of Annapolis (1750-1783). Tom plays brings the life and times of Annapolis to life with stories of the social and musical events that enriched the lives of this charming city. He also has a few stories about the fiery events in town that helped turn British America into the fledgling new nation.
Monday, June 4: History of the Schooner Woodwind from Dream to Reality, John Scarano and Ken Kaye 6:30-8:30
25 years ago, Ken, Ellen, and Jennifer Kaye had a dream realized with the building of the Schooner Woodwind at the Scarano Boat Yard, the second schooner that Scarano built. Listen to the Naval Architect and Designer of the boats talk with Ken Kaye about how they decided upon the hull design, sail plan, functionality and proportions of the Woodwind. John Scarano will talk about the beginning days of his family’s boatyard, and how it has grown to build more and more certified USCG vessels for entrepreneurs across the country. This will be the first time since Woodwind II was finished, that they will be in a relaxed atmosphere to reminisce about the dreams they both had 25 years ago and where they are now.
Monday, June 11: The Life of Frederick Douglass, William Ridgley 6:30-8:30
Frederick Douglass was described as a living counter-example that blacks we’re ignorant and unable to learn to read or write. Come learn how his everyday life was as a slave and how he was able to escape slavery.
CANCELLED (Boat privately chartered) Monday, June 18: Legends & Lore of the Annapolis Waterfront, Dave Gendell 6:30-8:30
Lifelong Chesapeake Bay sailor Dave Gendell brings aboard a boatload of stories of the Annapolis waterfront with a special focus on the Schooner America, wooden boatbuilding in Annapolis during World War II, and the personalities and events that make the waters off Annapolis one of the world’s most vibrant sailing grounds.
Monday, June 25: The Key to Annapolis History, Jeff Holland 6:30-8:30
The key to Annapolis history lies somewhere in the harbor… Jeff uses his original songs and narrative verse to tell three centuries worth of stories about Annapolis, some of which are actually true.
Monday, July 2: The Heyday of Bay-Front Beach Resorts, Stephanie Sperling 6:30-8:30
In the decades before the Bay Bridge was constructed, city people flocked to Anne Arundel County’s shores for summer recreation and relaxation. Many of the new communities included rustic cottages, dance halls, concert venues, gambling, and sandy swimming beaches. But most were segregated and closed after the passage of the Civil Rights Act. Learn about this complicated and fascinating history and how it affected our 21st-century landscape.
Monday, July 9: Tunes & Tales of the Golden Age of Annapolis, Tom Guay 6:30-8:30
On Schooner Woodwind’s History Monday cruises, Tom’s fiddle playing takes you on a trip back in time to The Golden Age of Annapolis (1750-1783). Tom plays brings the life and times of Annapolis to life with stories of the social and musical events that enriched the lives of this charming city. He also has a few stories about the fiery events in town that helped turn British America into the fledgling new nation.
Monday, July 16: Pirates of the Chesapeake Bay, Heather Ersts 6:30-8:30
Pirates have plied the waters of the Chesapeake Bay for hundreds of years and still do today. Hear tales of Black Beard, the town dubbed the “Nest of Pirates,” and today’s modern pirates as you sail along the same waterways they have sailed.
Monday, July 23: The Oyster Wars, William Ridgley 6:30-8:30
The oyster wars were series of sometimes violent disputes between oyster Pirates and authorities and legal Waterman from Maryland and Virginia in the waters of the Chesapeake Bay and the Potomac River from 1865 until around 1959.
Canceled (Boat privately chartered) Monday, July 30: The Maritime Republic of Eastport, Still revolting after all these years! Kevin Brooks 6:30-7:30
Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s interesting and downright fun history through the past four centuries. Historic forts, world-class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music-filled journey through the “Gulf of Eastport and Around the Horn”…(Horn Point that is…) sunset sail through history, music, and mirth.
Monday, August 6: The Tale of Two Cities, Janet Williman 6:30-8:30
Since 1845, America’s sailing capital and our Navy intertwined to engage with interesting characters from all of over the world. Delight in nautical skyline views; while discovering amazing, amusing and sometimes surprising stories. For example, a connection with the movie, King Kong is revealed during our sail.
Monday, August 13: Pirates of the Chesapeake Bay, Heather Ersts 6:30-8:30
Pirates have plied the waters of the Chesapeake Bay for hundreds of years and still do today. Hear tales of Black Beard, the town dubbed the “Nest of Pirates,” and today’s modern pirates as you sail along the same waterways they have sailed.
Monday, August 20: The Maritime Republic of Eastport, Still revolting after all these years! Kevin Brooks 6:30-8:30
Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s interesting and downright fun history through the past four centuries. Historic forts, world-class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music-filled journey through the “Gulf of Eastport and Around the Horn”…(Horn Point that is…) sunset sail through history, music, and mirth.
Monday, August 27: Legends & Lore of the Annapolis Waterfront, Dave Gendell 5:30-7:30
Lifelong Chesapeake Bay sailor Dave Gendell brings aboard a boatload of stories of the Annapolis waterfront with a special focus on the Schooner America, wooden boatbuilding in Annapolis during World War II, and the personalities and events that make the waters off Annapolis one of the world’s most vibrant sailing grounds.
Monday, September 3: The Tale of Two Cities, Janet Williman 5:30-7:30
Since 1845, America’s sailing capital and our Navy intertwined to engage with interesting characters from all of over the world. Delight in nautical skyline views; while discovering amazing, amusing and sometimes surprising stories. For example, a connection with the movie, King Kong is revealed during our sail.
Monday, September 10: Environmental History of the Bay, Alice Christman 5:30-7:30
How is the Bay? It’s a popular question to ask when you are cruising. But how has the Bay changed is also a good question? We’ll talk about the environmental history of the Bay, starting with what John Smith saw leading up to today. Hosted by the Chesapeake Bay Foundation.
When she is not working, she is found messin’ about on the Bay, where she races sailboats, catches sunsets, and finding daily inspiration to keep others inspired. Fair warning when you meet her: you will either end up being her best friend or hosting her as a guest speaker at a special event.
Monday, September 17: Steamboats and Ferries of the Bay, Jeff Holland 5:30-7:30
Steamboats and Ferries were once common on the Severn River. They transported people, agricultural produce, and the seafood bounty that made the Chesapeake famous. They also were part of the leisure travel industry that has brought tourist to our beautiful capital city on the water for 100s of years.
Monday, September 24: The Maritime Republic of Eastport, Still revolting after all these years! Kevin Brooks 5:30-7:30
Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s interesting and downright fun history through the past four centuries. Historic forts, world-class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music-filled journey through the “Gulf of Eastport and Around the Horn”…(Horn Point that is…) sunset sail through history, music, and mirth.
