Cruise through Maryland’s storied Chesapeake Bay aboard Experience Smith Island’s authentic boat tours. Taste fresh crab, meet watermen, and witness Bay wildlife up close on these hands-on trips departing from Crisfield.
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Difficulty
easy
Duration
3–4 hours
Fitness Level
Suitable for all fitness levels; minimal walking on flat terrain at island stops.
Wildlife
History
Smith Island is the last inhabited island in Maryland’s portion of the Chesapeake Bay, with a fishing tradition dating back six generations for some families.
Conservation
The boat tours emphasize sustainable interaction with Bay ecosystems and support watermen committed to responsible fishing and crabbing practices.
Experience Smith Island
Cruise through Maryland’s storied Chesapeake Bay aboard Experience Smith Island’s authentic boat tours. Taste fresh crab, meet watermen, and witness Bay wildlife up close on these hands-on trips departing from Crisfield.
Experience Smith Island is a Crisfield, Maryland-based tour operator specializing in authentic Chesapeake Bay experiences.
The company arranges guided boat trips to Smith Island and nearby waters, offering group tours, a 90-minute sunset cruise, a 25-minute Crisfield waterfront tour aboard the Circuit Rider, a six-hour Smith Island Tour with a crab cake lunch and hands-on demonstrations, and customizable private charters. Each trip highlights local culture, seafood heritage, and island wildlife, and includes experienced local guides and traditional Chesapeake Bay workboats.
Visitors can expect scenic boat rides, history-focused narratives, and interactive activities such as Smith Island Cake baking and blue crab catching demonstrations. The sunset cruise is led by Captain Everett Landon aboard a traditional workboat, providing narrated views of the Bay and regional stories. The Circuit Rider waterfront tour is conducted by a former waterman who explains Crisfield’s seafood industry and island connections on a short, informative route.
Experience Smith Island emphasizes authentic, place-based experiences that showcase Maryland’s waterway traditions. The business offers flexible options for groups, families, and special events, and promotes hands-on learning about local foods and maritime life. Reservations and custom charter inquiries are handled directly through the operator, allowing guests to design private or themed excursions.
Safety and local knowledge are central to the operation: tours use vetted vessels and experienced captains familiar with the Bay. The operator focuses on clear communication about trip duration, boarding locations in Crisfield, and inclusions such as meals and demonstrations. Booking details and schedules are available by contacting the operator.
Location
Crisfield, Maryland
Base for Smith Island departures
Workboat Tours
Circuit Rider & traditional boats
Authentic Chesapeake Bay workboats used
Trip Durations
25 min–6 hours
From short waterfront tours to full-day trips
Group & Custom
Group tours & charters
Custom charters available on request
Reserve a spot on a group tour, sunset cruise, waterfront tour, or custom charter departing Crisfield, Maryland.
Book in Advance
Capacity is limited on these intimate tours, so reserve your spot early, especially for weekend or group trips.
Wear Sun Protection
Bring sunscreen, a hat, and UV-blocking sunglasses to stay comfortable during open-water travel.
Bring a Camera
Keep a camera or smartphone ready – pelicans, crabs, and the coastal scenery are highly photogenic.
Stay Hydrated
Carry water or purchase refreshments to stay hydrated during the 3-4 hour trips, especially on sunny days.
Light Jacket or Windbreaker
Protects against cool breezes during early-season tours.
spring
Sunhat and Sunglasses
Necessary for sun protection on exposed decks during warmer months.
summer
Reusable Water Bottle
Keeps you hydrated throughout the multi-stop boat tour.
Camera or Smartphone
Capture the expansive wildlife and bay vistas.