You don’t have to own a boat to get out on the water on the Delmarva Peninsula. Here are a few easy options, available in ticketed fashion rather than by putting a group together and chartering a vessel.
• THE STEAM FERRY: The Patriot is a replica 1930s steam ferry that offers narrated cruises on various themes along the Miles River, sailing out of St. Michaels, Md. You board right near the entrance to the Chesapeake Bay Maritime Museum. Details and schedule.
• THE PADDLEWHEELER: The Choptank Riverboat Company runs Mississippi-River-style paddleboat cruises along the Choptank River. Lunch cruises, dinner cruises, murder-mystery cruises–there is quite a menu of themes. The paddlewheelers sail out of the dock at Suicide Bridge Restaurant, along the backroads of Dorchester County, Md.–kinda sorta near Hurlock. Details.
• 17TH-CENTURY STYLE: Delaware’s official tall ship, the Kalmar Nyckel is a meticulously crafter replica of a vessel that brought Swedish settlers to Delaware in the 1600s. It offers public sails out of Wilmington and New Castle, Del. in the warmer months. Details.
• SAIL A SKIPJACK: The Skipjack Nathan of Dorchester offers frequent public sails out of Cambridge, Md., Depart from pretty Long Wharf on the Choptank River. Details. (I can’t quite tell from the interwebs whether Capt. Ed Farley still offers skipjack cruises out of St. Michaels, Md. His website wasn’t showing any current cruises last I looked. You could check here to see if that’s changed.
• AN EARLY 1900s YACHT: The Chester River Packet is a 65-foot, 1920s-style yacht that does public sails out of Chestertown, Md. There is a whole slate of brunch, dinner, and special-occasion cruises on the calendar. Details.
• SEACRETS AT SUNSET: Seacrets of Ocean City, Md. has now added tiki-bar cruises to their entertainment-options empire. Think Sunset Cruises, Morning Mimosa Cruises, Rum & Reggae–you get the idea. Details.
• MORE OCEAN CITY: Find some more cruising options on this page put together by the folks at Ocean City tourism. Paradise Watersports is another possibility.
• WORKBOAT CRUIES: The Chesapeake Bay Maritime Museum in St. Michaels, Md. is offering 45-minute “Historic Workboat Experience Cruises” on select days during the summer months. Learn more and look for dates at this link, starting with May 15, 22, and 29.
• 18th CENTURY SCHOONER: The Sultana is a replica built from the plans of a schooner from the late 1700s that patrolled the Chesapeake Bay for the British. The crew there offers occasional two-hour public sails out of Chestertown, Md. Details.
• ON THE DELAWARE BAY: The folks at the popular Cape Water Tours offer a menu of themed adventures aboard the multiple vessels they sail out of Lewes, Del. Think eco-tours, dolphin watching, and much more. Details.
• MORE DELAWARE: A couple of more get-out-on-the-water options appear on this page put together by the folks at Southern Delaware Tourism.
Skipjacks on the Choptank by Jill Jasuta Photography–click on the photo to see more of her skipjack shots.
• SMITH ISLAND: Capt. Everett Landon dates his roots on the island back six generations. He’s been a waterman and a minister in the past. These days, his Experience Smith Island business offers a variety of themed boat tours focused on island life, culture, and nature. Details. For more of a self-guided experience, info on transport boats from the Smith Island tourism page can be found here.
• PELICANS: Delmarva Birding leads tours out to the spectacular brown pelican rookery near Smith Island, Md. in the middle of the Chesapeake Bay. Details. Another pelican-tour option is available through the outfit listed just above here, Experience Smith Island.
• TANGIER ISLAND: You can venture out to storied Tangier Island, Va. from boats that sail out of Crisfield, Md. (info here) or Onancock, Va. (info here).
• THE BARRIER ISLANDS OF VIRGINIA: The islands are an uninhabited natural wonder open to visitors who follow some easy eco-friendly rules that vary by season of the year. One option is Virginia Coast Ecotours (info here). Another is to hire a certified guide (info here).
–Freshly updated in April 2026. Originally posted by Jim Duffy in 2023 for Secrets of the Eastern Shore/Whimbrel Creations LLC.
