Explore the Chesapeake Bay Maritime Museum – Walk the docks, climb historic lighthouses, and check out classic Chesapeake boats

Stroll Talbot Street – Charming main street with boutiques, art galleries, and local shops

Grab drinks by the water at Foxy’s Harbor Grille – Laid-back, great views, perfect for a casual afternoon (one of our favorites!)

Dinner at The Crab Claw – Classic Maryland crab house experience right on the harbor

Bike around town or along the water – Easy, scenic, and a great way to explore

Sunset cruise on the Miles River – Relaxing way to take in the Chesapeake Bay views

Visit a local winery or brewery – Try St. Michaels Winery or nearby craft breweries

Stay or grab a drink at Inn at Perry Cabin – Beautiful waterfront property (you might recognize it from Wedding Crashers)

Kayak or paddleboard the harbor – Rentals available for a fun, active option

Enjoy fresh seafood everywhere – Oysters, crab cakes, and more are a must while you’re here