Smith Island Boat Tours & Sunset Cruises in Crisfield

Located at the edge of Maryland’s Chesapeake Bay, Crisfield stands as the gateway to Smith Island, the state’s only inhabited water-bound community. Experience Smith Island brings the natural rhythm and rugged lifestyle of these remote Bay waters to life through immersive boat tours that blend history, culture, and the region’s famed seafood industry. Set aboard a comfortable, well-maintained vessel captained by sixth-generation local Everett and his wife Carol Ann, the tours offer an authentic window into an often overlooked chapter of bay life. The flagship Smith Island Tour navigates through three small island communities, each with distinct character and workaday charm. Guests disembark for a fresh crab cake lunch in Ewell, witness a live crabbing demonstration at a working waterman’s shanty, and enjoy a hands-on Smith Island cake making presentation from a local family matriarch. Between stops, the waters teem with pelicans, blue crabs, and the occasional osprey, forging a connection to wildlife that is as pronounced as the sense of place. The Sunset Cruise invites travelers to experience the Bay at a slower pace, where the fading light casts long shadows on salt marshes and oyster beds while stories about the people who shape this landscape unfold. Whether you come for a couple’s getaway or a group excursion, the experience is rooted in genuine hospitality and deep local knowledge that breaks through the usual tourist veneer. In a region defined by shifting tides and disappearing waterfront communities, Experience Smith Island safeguards a living history and offers an engaging outdoor day on the water that captures the grit and grace of Maryland’s Eastern Shore shorescape.