Water Activities in Grasonville, MD

Take the helm for a relaxed cruise along the Annapolis waterfront

Celebrate the bride or groom aboard a historic private sailboat

Private Chesapeake Bay sailing aboard a 1935 ketch

Relax and cruise the South River on a spacious pontoon

Private evening on the water with sunset views from the South River

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

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

Sail the Miles River aboard a historic 1935 ketch

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

A relaxed captain-led ride through Chesapeake Bay tributaries to Annapolis

Cruise Chesapeake Bay coves and historic waterfronts en route to Galesville

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

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

Cruise Chesapeake Bay to Rock Hall with time to explore ashore

Cruise the Chesapeake Bay to explore historic St. Michaels by boat

See Chesapeake landmarks and explore historic Oxford by boat

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

See three historic lighthouses from the water

Paddle from Eastport or take a sit-inside kayak to your favorite spot

Cruise Kent Narrows waterways with local narration and panoramic views