Explore the timeless beauty and culture of Smith Island, Maryland

See the Chesapeake as you’ve never seen it before.

Experience Smith Island’s communities, traditions, environment and culture on our customized tours. Guided by local islanders onboard a classic deadrise workboat, our tours take you to the heart of the island’s beautiful, unforgettable landscapes and close-knit villages.

Video to show what Experience Smith Island LLC has to offer customers that book a tour day trip with us will experience.

Custom small-group experiences

From full-day island hopping excursions to pelican watching, Smith Island Cake baking demonstrations or fishing up soft shell crabs, our tours explore the people and places that make Smith magical.

Aerial picture of Ewell Smith Island MD showing the channel, boats, crab shanties, and businesses along the waterfront.

The Story of Smith Island

Smith Island, Maryland lies 12 miles offshore in the heart of the Chesapeake Bay. The island's small towns, Ewell, Tylerton, and Rhodes Point, were established as fishing and crabbing communities, relying on the bounty of the Bay for sustenance and livelihood. Over the years, Smith Island’s resilient inhabitants have preserved their unique culture, known for their distinct dialect, fishing methods and tradition of cake-making. Today, Smith Island remains a testament to the enduring spirit of coastal communities and their connection to the Bay.

Get the island’s insider experience.

With Smith Islanders as your guides, you’ll have access to authentic behind-the-scenes experiences. From listening to watermen’s fishing stories to learning a family recipe for Smith Island cake, our tours are designed to give you a true taste of island life. We know the people, the places, the captains, and everything else that is needed to make for an amazing visit.

Meet Your Experience Smith Island Guides

We’re Everett and Carole Ann Landon, born and raised Smith Islanders who are passionate about sharing our unique heritage.

We can’t wait to explore Smith Island with you!

Owners of Experience Smith Island LLC in the boat Circuit Rider with sign displaying their website at the stern of the boat.

Guest Feedback

  • Rhodes Point MD

    What a truly incredible experience…The experience Everett and Carol Ann Landon and her family have created is as close as you can get to some of the best people on this planet. The history and immersing tour should be a right of passage for any Marylander. The views were only topped by the hospitality of everyone we encountered.—K. Flayhart

  • What a great trip! Captain Everett and Carol Ann are gracious hosts that provide a wealth of knowledge about all three communities of Smith Island. I especially enjoyed the crabbing and cake demonstrations. This experience is a MUST when you visit Somerset County, MD. —A. Riggin

  • Our group had a lovely day, exploring the three villages of Smith Island. Everett and Carole Ann were gracious hosts, sharing the place that they both grew up in. It was a great way to tour the remote island on a different schedule than offered by the regular cruise from the mainland and allowing for greater exploration.— Wendy Robertson

  • Captain Everett flawlessly navigated our three-hour tour. He narrated a wonderfully informative visit to each of Smith Island's three settlements sharing the culture, values, history and facts about the watermen and their craft, including a stop at his father's Rhode's Point crab shanty where he demonstrated crabbing equipment and pots and described the troubled industry in detail —Joel Schlesigner

  • For more client feedback and reviews, check out our Google page!

    Google Reviews