Last updated: August 10, 2026
Thing to Do
Historic 1935 Lady Patty Sailing Charter
Laura’s Focus Photography
St. Michaels Sailing Charters offers visitors an opportunity to experience the Chesapeake Bay aboard Lady Patty, a beautifully restored wooden ketch built in 1935 on Maryland's Western Shore. Departing from historic St. Michaels, this Chesapeake Gateways Experience combines authentic sailing with interpretation of the Bay's natural, cultural, and maritime heritage.
Each sail invites visitors to experience the Chesapeake as generations of mariners have, powered by the wind while exploring the Miles River and surrounding Bay waters. Small group charters encourage conversation with the captain and crew, who share stories about Chesapeake shipbuilding, working waterfronts, navigation, local wildlife, and the communities that have depended on these waters for centuries. Along the way, visitors observe changing shorelines, tidal habitats, birdlife, and historic landmarks while learning how the Bay continues to shape the region's culture and economy.
Built as an offshore racing yacht, Lady Patty spent decades sailing and racing across the Chesapeake before transitioning into a cruising vessel. Today, the vessel serves as a living example of traditional wooden boat craftsmanship and Chesapeake maritime history.
As part of the Chesapeake Gateways Network, Lady Patty Sailing Charters connects visitors with the Chesapeake Bay through recreation, interpretation, and stewardship. Each voyage encourages a deeper appreciation of the Bay's history, ecology, and enduring importance while inspiring care for this nationally significant watershed. Learn more by visiting their website.
Each sail invites visitors to experience the Chesapeake as generations of mariners have, powered by the wind while exploring the Miles River and surrounding Bay waters. Small group charters encourage conversation with the captain and crew, who share stories about Chesapeake shipbuilding, working waterfronts, navigation, local wildlife, and the communities that have depended on these waters for centuries. Along the way, visitors observe changing shorelines, tidal habitats, birdlife, and historic landmarks while learning how the Bay continues to shape the region's culture and economy.
Built as an offshore racing yacht, Lady Patty spent decades sailing and racing across the Chesapeake before transitioning into a cruising vessel. Today, the vessel serves as a living example of traditional wooden boat craftsmanship and Chesapeake maritime history.
As part of the Chesapeake Gateways Network, Lady Patty Sailing Charters connects visitors with the Chesapeake Bay through recreation, interpretation, and stewardship. Each voyage encourages a deeper appreciation of the Bay's history, ecology, and enduring importance while inspiring care for this nationally significant watershed. Learn more by visiting their website.
This location does not accept the America the Beautiful—National Parks and Federal Recreational Lands Pass. Entrance fees and ticket policies are set independently by the managing partner, as detailed on their website.
Details
Duration
2-7 Hours
Most sailing charters are 2-hour duration, but they offer options for half-day and full-day sailing experiences.
Activity
Sailing
A guided sailing tour on the Chesapeake Bay
Age(s)
Yes, children of all ages are welcome on all their family-friendly trips
Pets Allowed
Yes with Restrictions
Pets are only permitted on private charters and cannot be accommodated on per-person or shared sails.
Activity Fee
Yes
Sailing charters start at $95 per person.
Location
101 N Harbor Rd. St. Michaels, MD 21663
Reservations
Yes
Reservations are recommended due to limited seating capacity. Book online or call 410-849-9864
Season
Spring, Summer, Fall
They sail 7 days a week from mid-April into November. Book online or call at 410-849-9864
Time of Day
Day, Dusk
They offer 3 day-time sails followed by a sunset sail which ends at dusk.
Accessibility Information
The yachts are not accessible to wheelchairs. Participants should be able to walk and step up/down a handful of steps to safely board our sailboat. If your guest is completely wheelchair bound, then we recommend you call the charter at 410-849-9864 to discuss your personal needs. Once aboard guests can sit back and relax for the majority of the experience.
Tags:
chesapeake bay ,
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maryland,
boating,
education and science,
environmental literacy,
heritage,
maritime,
on the water,
public access,
rivers,
scenic views,
stewardship,
trails and tours,
watching wildlife,
water,
watersheds