things to do in Saint Leonard, MD

Private Chesapeake Bay sailing aboard a 1935 ketch

Paddle a brackish waterway beside Blackwater Refuge

Paddle the Little Blackwater River and watch for wildlife along its banks

Explore Deale's creeks and bay at your own pace on a paddle board

Sail the Miles River aboard a historic 1935 ketch

Paddle Dorchester County waterways with equipment delivered to your location

Greet the day with a guided paddle at sunrise on Chesapeake Bay

Plan a private proposal aboard a historic 1935 ketch

Reach shallow fishing spots beyond the reach of deeper-draft boats

Paddle the creek, then pause at a local waterfront restaurant for brunch

Launch from a private ramp less than a 10-minute paddle from Chesapeake Bay

Sail a historic ketch at sunset with champagne and Chesapeake Bay views

Private catamaran sailing with harbor views and Miles River breezes

Sail the Miles River aboard a spacious catamaran

Harbor views and wind-powered sailing on the Miles River

Savor rotating craft beer tastings aboard the historic Lady Patty

Build Practical Sailing Skills With Private, Hands-On Instruction

Take the Helm and Learn Hands-On Sailing Skills

Make your vows your own aboard a private Chesapeake Bay catamaran

Exchange vows aboard a historic sailboat with a ceremony shaped around you

Bottom-fish with room to cast on a 16-angler boat

Bring your group together for a laid-back escape on the water

Take the controls for a Chesapeake Bay jet ski ride

A Chesapeake Bay seafood feast with traditional Smith Island flavors