It takes only a few hours spent along its lapping waters, soaking up the peace and natural beauty, to realize that the bay’s highlights include much more than just fabulous seafood. Whether dipping a paddle into a pristine creek or learning about the region’s rich history aboard a magnificent vessel, the Eastern Shore of Maryland and Virginia is home to trips designed to celebrate its treasures. So if you’re searching for adventure, or wanderlust has captured your heart, consider one of our top 10 tours of the Chesapeake Bay. You'll come away with memories that will serve as reminders of just how lucky we are to have this spectacular attraction in our midst.
Sail Selina II (St. Michaels)
The Tour: A sail on the Selina II is a trip back to the Gatsby-era, when elegant wooden yachts plied the bay and ladies called everyone “dahling” instead of “hon.” These days, the 41-and-a-half-foot-long yacht—the world’s largest surviving vintage catboat, according to its owner and captain, Iris Clarke—makes for a relaxing sail out of St. Michaels. On the two-hour afternoon tour, depending on wind conditions, the six-passenger, single-masted boat either heads up the Miles River or past the ritzy waterfront mansions along Leeds Creek. Clarke offers several tours, including a sunset champagne cruise and a unique beer-tasting cruise, during which voyagers get to sample up to a half-dozen Eastern Shore microbrews. Your Guide: The Selina II has been in Clarke’s family since her “fabulously wealthy” grandparents had it commissioned in 1926. Captain Iris peppers her tours with ample info about the yacht’s history, local sea life, and copious amounts of adult beverages. “I’m a fount of information,” she says, “as well as beer and wine.” Highlight: As much as we like the beer-themed trip, the Moonlight Cruises, offered once a month when the moon rises as the sun sets, are magical. “Watching the stars come out is like watching a photograph develop before your eyes,” notes Clarke. Details: Prices vary by tour. 101 N. Harbor Rd., 410-726-9400
Parkers Creek Guided Canoe Trip (Prince Frederick)
The Tour: Located about an hour-and-a-half’s drive from Baltimore, Parkers Creek is a beautiful anomaly: one of the last undeveloped tributaries on the bay’s western shore. The 3,000 acres abutting the creek have been preserved and protected by the nonprofit American Chestnut Land Trust (ACLT). You can hike the trails throughout the property, but the best way to see the area is on an ACLT-led canoe tour of the creek. Paddlers launch from a beach on the bay and then enter the quietly flowing creek, paddling upstream. The three-hour roundtrip weaves through salt marsh and wooded wetlands that look much the same as they did 400 years ago, when explorer John Smith passed by. Your Guide: A rotating cadre of knowledgeable guides from the ACLT ensure even rookie paddlers are looked after, as they point out the variety of waterfowl and wildlife and talk about how the tributary has remained so well-preserved. Highlight: The unspoiled wilderness and serenity can’t be beat. On a trip last fall, we spotted roughly a dozen bald eagles soaring above the waterway. Details: Canoe trips depart several Saturdays per month, spring through fall. Tours are free, but there is a suggested $15 donation per person. Scientists’ Cliffs Rd., 410-414-3400
The Tour: If you’ve ever wondered how soft-shell crabs get from the water to your plate, join Butch and Macy Walters on one of their Crab-Bytes tours, which give crab lovers a front-row seat to the business. Tourgoers can help Butch haul up peeler pots in a tributary of the bay, or join Macy at the family’s crab shanty to see how the crustaceans shed their shells and are sorted for market. The three-hour tour on the couple’s 40-foot deadrise out of Chance allows the Walterses to share their way of life. “It’s an opportunity for us to tell our story,” says Macy. Best of all, you can buy what you catch. Your Guides: Butch is a fifth-generation waterman and Macy also can trace her maritime pedigree back four generations. “Working the water is all we know how to do,” she says. Highlight: Hauling up a pot full of crabs makes for great Facebook photos, but hearing the Walters family lore is likely what you’ll remember most. Ask Macy about her grandfather, Captain Biscuit, who earned his nickname by eating a pan of home-baked biscuits every day. Details: Tours run May through October. Oyster-dredging tours are offered during winter months. $50 per person, Eldon Willing Rd., Chance, 410-430-6788