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How and Where to Find Eastern Shore Cruises in Maryland

Ships ahoy! Get your sea legs with these water excursions.

Sunset from boat ride on Maryland's Eastern Shore
Photo by Renee Sklarew

Whether you want to paddle yourself or sit back and relax, these Maryland boating companies have options for Eastern Shore cruises that promise a great day on the water.

Kent Narrows Rentals  

Kent Island

Dreamed of sleeping overnight on a houseboat on the bay? This outfitter has two well-equipped houseboats for rent at the Kent Narrows Bridge, walking distance to the waterfront bars and fishing charters. The houseboats are suspended on the dock for a stable experience. Choose a one- or two-bedroom, both with patios for watching the sunset. Rates start at $179 per night. 

St. Michaels Harbor Shuttle  

St. Michaels  

Behold the awesome beauty of a St. Michaels sunset on Harbor Shuttle’s BYOB Sunset Cruise. The 75-minute tour departs from the port on Mulberry Street near Blu Miles Seafood & Grill, where you can pick up supplies for an onboard picnic. Groups and pets are welcome. There’s also a one-hour, narrated History & Folklore cruise. Sunset cruise runs $45 per person. 

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Let’s Go Crabbing   

Tilghman Island  

Charter a day of crabbing with a Coast Guard–certified captain on the 42-foot Riley Kat. Capt. Russell Dize motors to the top spots and teaches his passengers how to use the traditional trotline. Dize, a sixth-generation waterman, provides bait, nets — and hopefully sends you home with a bushel of tasty crabs. Rates are $600 per charter, with up to six guests.  

Choptank Riverboat Company  

Hurlock  

Roll down the scenic Choptank River on a reproduction of an 80-foot paddle wheeler. The company has two heated, air-conditioned boats, with a variety of options, from sightseeing to a crab feast to themed cruises — murder mystery on the water anyone? Public and private cruises run from April through December and depart from Suicide Bridge Restaurant. Rates start at $32 per person.  

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The Oxford-Bellevue Ferry   

Oxford   

At 341 years, The Oxford-Bellevue Ferry is the oldest privately owned ferry service in the country. Cars, bikes, motorcycles, and people are welcome for this 10-minute ride across the Tred Avon River. Be forewarned: The ferry closes by sunset. Pedestrians ride for $8 roundtrip.  

Dockside Boat Rentals  

Multiple counties   

Rent stand-up paddleboards, kayaks, and Rigid Inflatable Boats from this Oxford-based family business. Dockside will deliver your rented boat directly to your vacation home’s dock. Along with the rental, you can reserve safety gear like life jackets and dry bags to protect your valuables. Prices vary depending on the boat and duration.  

Blackwater Adventures Chesapeake Bay   

Cambridge  

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This outfitter has options, whether it’s a guided tour through the pristine waters of the Blackwater National Wildlife Refuge, or a heart-pumping jet ski ride from the Hyatt Regency Chesapeake Bay Resort in Cambridge. Guides provide instruction and lead you on kayaks to quiet coves with a bevy of wildlife. Choose a wine-tasting tour from Layton’s Chance Winery, a fishing expedition, or an all-day kayak and bike tour for the full Eastern Shore experience. Kayak tours start at $80; jet skis $95 for 30 minutes.  

Feature image by Renee Sklarew

This story originally ran in our May issue. For more stories like this, subscribe to Northern Virginia Magazine.

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