things to do in Saint Michaels, MD

Plan a private proposal aboard a historic 1935 ketch

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

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

Paddle Dorchester County waterways with equipment delivered to your location

Private catamaran sailing with harbor views and Miles River breezes

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

See three historic lighthouses from the water

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

Private Chesapeake Bay sailing aboard a 1935 ketch

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

Cruise Kent Narrows waterways with local narration and panoramic views

Customize a shaded private outing on the Upper Choptank River

Walk Easton's haunted past through its notorious Tragedy Triangle

Launch from Eastport or paddle at your favorite spot

Toast the evening on a Chesapeake Bay cruise with an onboard full bar

Paddle together at your favorite Annapolis-area spots

Celebrate your occasion aboard a private party boat on Chesapeake Bay

A flexible tandem kayak rental for paddling together