An easy walk from the Inn at Perry Cabin or any of the hotels we recommend, Saint Michaels has plenty of local shops, galleries, and eateries you won’t want to miss.

Sailing, cruising, kayaking, paddle boarding, fishing, and crabbing are all available for those who love the water. Sail Selena II, Patriot Cruises, St. Michaels Harbor Shuttle, and Shore Pedal and Paddle are options for whatever type of water experience you seek.

Saint Michaels is rich in early American history. There are several museums in the quaint downtown area, including the Chesapeake Bay Maritime Museum, which is home to the Hooper Strait Lighthouse and Waterman’s Wharf, and the Saint Michaels Museum.

Miles of great hiking and biking are near by. Some of our recommended hotels have bikes available for guests, but if you are staying at an Airbnb or VRBO, you can rent bikes at Shore Pedal and Paddle. You can also walk the 2.5 mile St. Michaels Nature Trail if you’d like to venture beyond the downtown area on foot.

For those wishing to extend their time in and around Saint Michaels, there are several small towns worth visiting within a 30 mile radius. Easton, the county seat of Talbot County, is a 20 minute drive from Saint Michaels. You will find upscale shops and restaurants, history, arts, cultural attractions and picturesque streets in this delightful town. Tilghman Island, also a 20 minute drive from Saint Michaels, is like going back in time to an original waterman’s village. This scenic village lets you know what life was like when crab was king in the Chesapeake region.