About Us


Everett and Carole Ann Landon

Experience Smith Island Founders & Guides

Owners of Experience Smith Island LLC in boat at dock.

Carole-Ann and Everett Landon both share deep roots on Smith Island. Carole-Ann can trace her ancestry on her paternal side back at least four generations, and Everett estimates at least six generations on both sides of his family tree. Their family roots are deeply embedded in the island's maritime heritage, with multiple generations harvesting the Bay’s bounty as watermen. 

For Carole-Ann, her memories are shaped by the island’s close-knit community and natural beauty of the island. She fondly recalls family gatherings and the unique experience of growing up surrounded by the Bay.

Everett enjoys the distinct way of life on Smith Island, characterized by a tight-knit community, self-sufficiency, and a deep respect for nature. As a former preacher for the island himself and a descendant of Joshua Thomas, the famous Chesapeake “Parson of the Islands,” the community’s deep faith is a defining element of island life, with everyone pitching in to help each other in times of need. For Everett, the island's tranquility and the necessity of living in harmony with nature are particularly unique, especially in contrast with the fast-paced mainland life. Despite initially taking their experiences as Smith Island natives for granted, both Carole and Everett have grown to  appreciate the island's treasures and seek to share its beauty with others.

Driven by a desire to showcase the island's uniqueness and beauty, Carole-Ann and Everett founded Experience Smith Island. Over time, the business has evolved into a meaningful way to preserve their heritage and provide for their family. As guides, they strive to offer visitors an authentic glimpse into island life, fostering an appreciation for Smith Island's culture, history, and natural beauty.

Experience Smith Island is proud to be trained & certified by the following organizations

Goup waving as boat is leaving the dock from Smith Island Maryland

Our Vessel

Circuit Rider is a 35’ fiberglass dead rise boat built for commercial fishing in the waters of the Chesapeake Bay. She was built by Eugene Evans of Evans Boats of Crisfield, MD (Evans was born on Smith Island and is Capt. Landon’s cousin). 

The name Circuit Rider was given to early American Methodist clergy who would travel on a “circuit” to several communities to minister and preach the Gospel of Jesus Christ. Captain Landon is a former preacher on the island who made his rounds, or circuit, to the three communities each Sunday.

The name is also a nod to Captain Landon’s great great great grandfather, Joshua Thomas—known as the “Parson of the Islands”—who sailed to the island communities in his log canoe The Methodist to preach the gospel.

Owner of Experience Smith Island LLC and Captain  of the Circuit Rider boat looking out the cabin window

Captain Everett Landon provides a safe and comfortable ride for Experience Smith Island passengers aboard Circuit Rider