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 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.
Sailing Schedule for History Mondays 2022:
Monday, May 2: The Key to Annapolis History, Jefferson Holland 5:30-7:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
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Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, May 9: Working Women of Colonial Annapolis, Heather Ersts 5:30-7:30
Before the American Revolution, Annapolis was full of a cast of colorful women working to make ends meet. Hear their stories, their triumphs, and tragedies, and then walk in their footsteps along Annapolis streets and into their homes and workplaces, that still exist today. Heather Ersts is Chesapeake born and raised, is happiest on a boat, and loves the smell of low tide. She is a social historian with multiple degrees, lots of random information in her head, and way too many books in her house.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, May 16: The Key to Annapolis History, Jefferson Holland 6:30-8:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, May 23: Schooners, Yawls and Ketches Oh My, Michael John Williams 6:30-8:30
The history of the schooner is very much the history of America. Invented by the Dutch in the 16th or 17th century, the schooner was further developed, and one could say, perfected in North America. The schooner came into extensive use in New England from the early 18th century onward, helping young America develop into a trading nation. Built for speed and windward ability, the schooner was a backbone of the early American economy participating in trading, slaving, privateering, blockade running, and offshore fishing. In the Chesapeake Bay region, several special types of schooners such as the Baltimore clipper, the bugeye, and the pungy developed. In this history Monday sail, Prof. Mike Williams of Syracuse University, will explore the history of the schooner covering how the schooner and its rig developed, the construction of schooners over the centuries and their evolution from working boats into leisure yachts. He’ll also touch on the wider evolution of working boats such as cutters, ketches and yawls into the pleasure craft we love and enjoy today. Michael Williams is Associate Professor of International Relations at Syracuse University. A native New Englander and sailor, Michael spent summers in Vineyard Haven, MA a wooden boat Mecca and has been consumed by the craft of wooden boats since childhood.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, May 30: The Key to Annapolis History, Jefferson Holland 6:30-8:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, June 6: Legends & Lore of the Annapolis Waterfront, Dave Gendell 6:30-8:30
Annapolis sailor and author David Gendell brings aboard stories of Annapolis, the Naval Academy, sailing, and the people who make the Chesapeake Bay one of the world’s most vibrant sailing grounds. David Gendell is a lifelong Annapolis sailor. He is the co-founder of SPINSHEET and PROPTALK magazines. He is the author of THOMAS POINT SHOAL LIGHTHOUSE, the only book devoted to the iconic lighthouse located in the Chesapeake Bay off Annapolis.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, June 13: The Key to Annapolis History, Jefferson Holland 6:30-8:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, June 20: Pirates on the Chesapeake, Heather Ersts 6:30-8:30
As you sail the Chesapeake, hear tales of the swash-buckling pirates who sailed these waters before you. The ferocious Blackbeard, reluctant founders of the College of William and Mary, and the brave and bold who were the Nest of Pirates are just a few. Heather Ersts is Chesapeake born and raised, is happiest on a boat, and loves the smell of low tide. She is a social historian with multiple degrees, lots of random information in her head, and way too many books in her house.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, June 27: Battle of the Severn, Steve Carr 6:30-8:30
Learn the forgotten story of the lost town of “Providence”, the first Annapolis. The Battle of the Severn was a bloody skirmish fought on March 25, 1655, on the Severn River at Horn Point (today’s Eastport). It was an extension of the conflicts that formed the English Civil War, pitting the forces of Puritan settlers against the Catholic forces aligned with Lord Baltimore, then Lord Proprietor of the colony of Maryland. It was the only battle of the English Civil War fought in North America and the last clash of that nine-year struggle for religious rule. Steve Carr was born and raised in Annapolis, attended the Naval Academy, and worked at the Grand Canyon for fifteen years. Steve is the author of six books, including the very popular book about the Chesapeake entitled “Water Views”. He was a columnist for “Bay Weekly”. He is also is a travel writer and performs on stage in Washington, D.C. as part of “Story District”.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, July 11: Birds of the Chesapeake, Heather Ersts 6:30-8:30
On the Atlantic Flyway, a superhighway of the bird world, the Chesapeake is rich with all kinds of birds. Chesapeake birds have adorned the rich and famous’ heads and tables for decades survived chemicals, and remain highly sought after prizes. Hear tales of our feathered friends, and catch sightings of them, as we sail their home waters. Heather Ersts is Chesapeake born and raised, is happiest on a boat, and loves the smell of low tide. She is a social historian with multiple degrees, lots of random information in her head, and way too many books in her house.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, July 18: The Key to Annapolis History, Jefferson Holland 6:30-8:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, July 25: Bay Ridge of the Chesapeake- “the Queen Resort”, Carol Patterson 6:30-8:30
An account of the turn-of-the-century decades when Bay Ridge flourished as a grand Victorian resort served by steamship and train. Carol Cushard Patterson received her B.A. and M.A. degrees in English Literature from the University of Maryland. She and her husband Noel live in Bay Ridge, Annapolis, where they raised two children and now have three grandchildren. Carol is co-author, along with Jane Wilson McWilliams, of Bay Ridge on the Chesapeake, 1986. Over the past 35 years she has given numerous talks, lectures, and slide presentations about the Bay Ridge Victorian resort, including those for the l999 Heritage Lecture Series of the Cultural Heritage Alliance, The Chesapeake Bay Maritime Museum, Annapolis History Consortium, the 2020 Winter Lecture Series of Annapolis Maritime Museum, and as guest speaker aboard the schooner Woodwind during summer evening cruises to Bay Ridge.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, August 1: Providence: The Original Annapolis, Drew Webster, 6:30-8:30
Did you know that Annapolis was originally located on the other side of the Severn River? Known as Providence, the original English settlement was established in 1649 near Greenbury Point. Join us as we learn what history and archaeology can tell us about the first colonial settlement in Anne Arundel County — one that would later become the Capital of Maryland. Drew Webster is an archaeologist with Anne Arundel County’s Cultural Resources Section and the Lost Towns Project nonprofit. He has a Master’s degree in Historical Archaeology and is currently pursuing a Ph.D. at the University of Maryland, College Park. He loves using artifacts to tell the stories of everyday people in the past.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, August 8: The Key to Annapolis History, Jefferson Holland 6:30-8:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, August 15: Battle of the Severn, Steve Carr 6:30-8:30
Learn the forgotten story of the lost town of “Providence”, the first Annapolis. The Battle of the Severn was a bloody skirmish fought on March 25, 1655, on the Severn River at Horn Point (today’s Eastport). It was an extension of the conflicts that formed the English Civil War, pitting the forces of Puritan settlers against the Catholic forces aligned with Lord Baltimore, then Lord Proprietor of the colony of Maryland. It was the only battle of the English Civil War fought in North America and the last clash of that nine-year struggle for religious rule. Steve Carr was born and raised in Annapolis, attended the Naval Academy, and worked at the Grand Canyon for fifteen years. Steve is the author of six books, including the very popular book about the Chesapeake entitled “Water Views”. He was a columnist for “Bay Weekly”. He is also is a travel writer and performs on stage in Washington, D.C. as part of “Story District”.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, August 22: The Key to Annapolis History, Jefferson Holland 6:30-8:30
Discover why Annapolis is what it is today as Jefferson Holland leads you through 400 years of local history through humorous stories, songs, and poetry. Jefferson Holland is a modern-day Chesapeake Troubadour: singer, songwriter, poet, story-teller, performing all original material inspired by decades of life on the Bay. Jeff has served as the director of the Annapolis Maritime Museum, as the Riverkeeper for the West and Rhode Rivers, and a Research Associate at the Smithsonian Environmental Research Center.
More Info
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, August 29:
Legends & Lore of the Annapolis Waterfront, Dave Gendell 5:30-7:30
Annapolis sailor and author David Gendell brings aboard stories of Annapolis, the Naval Academy, sailing, and the people who make the Chesapeake Bay one of the world’s most vibrant sailing grounds. David Gendell is a lifelong Annapolis sailor. He is the co-founder of SPINSHEET and PROPTALK magazines. He is the author of THOMAS POINT SHOAL LIGHTHOUSE, the only book devoted to the iconic lighthouse located in the Chesapeake Bay off Annapolis.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, September 5: What You See Around You- History Cruise hosted by the Captain & Crew, 5:30-7:30
When the History Speaker cancels, we get the chance to take a deep dive into the history that you will see specifically on the cruise. We will talk about the old radio towers, seaplanes on the Severn, the Victorian resort on Bay Ridge, the area where George Washington ran aground and so much more. The Captain and Crew will be sharing stories, fun facts, and humor that is heavily slanted to the history that you can see and what was once there.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, September 12: What You See Around You- History Cruise hosted by the Captain & Crew, 5:30-7:30
When the History Speaker cancels, we get the chance to take a deep dive into the history that you will see specifically on the cruise. We will talk about the old radio towers, seaplanes on the Severn, the Victorian resort on Bay Ridge, the area where George Washington ran aground and so much more. The Captain and Crew will be sharing stories, fun facts, and humor that is heavily slanted to the history that you can see and what was once there.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
Monday, September 19:
Legends & Lore of the Annapolis Waterfront, Dave Gendell 5:30-7:30
Annapolis sailor and author David Gendell brings aboard stories of Annapolis, the Naval Academy, sailing, and the people who make the Chesapeake Bay one of the world’s most vibrant sailing grounds. David Gendell is a lifelong Annapolis sailor. He is the co-founder of SPINSHEET and PROPTALK magazines. He is the author of THOMAS POINT SHOAL LIGHTHOUSE, the only book devoted to the iconic lighthouse located in the Chesapeake Bay off Annapolis.
Tickets go on Sale 6 Days In Advance, Buy Tickets Now
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