Travel & Outdoors

Bay Window

These 10 tours immerse visitors in the wonders of the Chesapeake Bay.

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

Crab-Bytes (Chance)

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


If you want a (wet) thrill, climb onto the netting and you’ll feel like you’re flying.

Chesapeake Sailing Tours (Arnold)

The Tour: Trimarans—three-hulled, sail-powered boats—are an uncommon sight on the Chesapeake, which is what makes a trip aboard the Dragonfly such a unique experience. The 27-foot-long boat is one of the fastest crafts on the bay, but its multi-hull design also makes it one of the more stable. On a two- or three-hour daytime or sunset sail along the Magothy River and out in the bay, you’ll speed past the Baltimore Harbor Light, keep an eye out for stingrays and jumping fish, and gawk at the million-dollar homes along Gibson Island. If you want a (wet) thrill, climb onto the netting between hulls and you’ll really feel like you’re flying over the water. Your Guide: Captain Dan Tobin earned his sailing cred while leading charter boat tours in Florida for about a dozen years. He has been cruising the Chesapeake on Dragonfly for almost 10 years. Highlight: Tobin lets willing passengers take the helm or trim the sails. “It’s always fun when we pass some multimillion-dollar sailboat with a little kid steering,” he says. Details: $250 for up to four passengers for a two-hour trip, $75 an hour after that; includes a $20 gift certificate to Deep Creek Restaurant & Marina. 1050 Deep Creek Ave., 410-349-4360

Wm. B. Tennison (Solomons)

The Tour: Buyboats used to be ubiquitous on the Chesapeake. The sturdy crafts would cruise around the bay, purchasing oyster caches so watermen wouldn’t have to return all the way to port to sell their catch. The Wm. B. Tennison, built in 1899, spent most of her life doing just that, but these days, she runs tours out of the Calvert Marine Museum in Solomons. The one-hour voyages are a relaxing way to explore the Patuxent River, while cruising past the Navy Recreation Center, busy Solomons harbor, and under the 135-foot-tall Governor Thomas Johnson Bridge. Your Guide: Captain Don Prescott, who has piloted the Tennison since the late 1990s, does the heavy lifting, while mates relate the history of the boat, and point out prominent sights. Highlight: Just getting a chance to sail on a 118-year-old bugeye, the predecessor to the skipjack, is a pretty cool experience. The Tennison’s sails were swapped out for an engine in the early 20th century, but the nine huge logs that comprise her hull—instead of the frame-and-plank type of construction used more frequently for bugeyes—remain. In fact, she’s the only Coast Guard-licensed log-hulled vessel in the United States. Details: Tours depart from the museum dock at 2 p.m., Wednesday through Sunday, May through October, with additional cruises on summer weekends. $7 for adults; $4 for children, 5-12. 14200 Solomons Island Rd., 410-326-2042

Sultana Public Sails (Chestertown)

The Tour: The original Sultana patrolled the coastline of Colonial North America from 1768 to 1772 enforcing the despised Townshend Acts, a series of acts that most notably imposed taxes on colonists. This exact replica, launched in 2001, cruises the Chester River with a much more benign purpose: educating audiences on the ecology of the bay. During the week, the Sultana hosts myriad school kids, but on Saturdays from spring through fall, it’s time for kids of all ages to have fun. Best bet is the late morning Ecology Sail, during which the crew drags a net behind the boat and pulls up crabs, catfish, choker, eels, and other river critters, and plops them into an on-board tank. This allows passengers to see, touch, and learn about them firsthand before depositing them back into the water. Your Guide: Captain Michael Fiorentino and a complement of mates let passengers hoist sails or take the helm, while relaying historic information about the boat and the ecology of the river. Captain Mike also worked on the Pride of Baltimore II and captained the Lady Maryland, but he had another life before he found the sea: Fiorentino once designed sets for Broadway shows. Highlight: Like any good Colonial-era schooner, the Sultana packs some punch: During the tour, the crew fires off the swivel gun. (Hold your ears!) Details: Public sails depart Saturdays, April through October. $30 for adults; $15 for kids under 12. 105 S. Cross St., 410-778-5954


“I like to get people out of their comfort zones. I like to blow minds.”

Chesapeake Lights (Tilghman Island)

The Tour: The best way to take in the majesty of a real Chesapeake lighthouse is from the water, of course. Captain Mike Richards offers four different lighthouse adventures in scope and length from 13 lights over two days (for lighthouse fanatics only; you know who you are) to five-hour trips that visit beaming beacons along the mid-Eastern Shore to a one-and-a-half-hour sunset trip that just stops at Sharps Island Light. “We get so close you can see the rivets,” says Richards. Your Guide: Few people know more about Chesapeake lights than Richards, who has been leading these tours on the MV Sharps Island—his stout, former U.S. Navy Special Forces boat—for about 14 years. Best of all, you can combine a tour with an overnight at Tilghman Island’s The Lazyjack Inn, which Richards runs with his wife, Carol. Highlight: Seeing a lighthouse close up should be on every Marylander’s bucket list. Added bonus: Motoring under the Bay Bridge on a busy summer weekend is far more pleasant than crossing it. Details: Tours range from $40 for the Sunset Pursuit trip to $280 for the two-day tour. Locations vary, 410-886-2215

Captain Barry’s Backbay Cruises (Chincoteague Island, VA)

The Tour: This isn’t a sit-back-and-relax boat ride. On a trip with Captain Barry Frishman, you can expect to get dirt on your hands and mud between your toes. Frishman, who has been called the “Indiana Jones of the Chincoteague,” is on a mission to expose people—both kids and adults—to nature as closely as possible. That means docking his pontoon boat on sandbars and digging for clams, foraging for snails and hermit crabs, and learning how to shuck—and slurp—an oyster. “There’s a whole generation of kids growing up on laptops,” he says with despair. “I like to get people out of their comfort zones. I like to blow minds.” Your Guide: Frishman, who has been operating these tours for more than 25 years, is a whirlwind of energy and an encyclopedia of Chincoteague wildlife. He keeps the tours limited to six, so he can “crawl around on his hands and knees” with every passenger. Highlight: You’ll likely remember Frishman just as much as the trip itself. (Take a selfie with him before disembarking.) Photo ops of seabirds and water views are plentiful. You can even snap one of your kid holding a live jellyfish—the kind that doesn’t sting. Details: The two-hour tours depart five times daily during summer. $40 per adult and $35 for kids 11 and under. 6262 Marlin St., 757-336-6508

Kayak Winery Tour (Cape Charles, VA)

The Tour: We don’t usually endorse mixing booze with water sports, but kayaking and sampling wines on SouthEast Expeditions’ Kayak Winery Tour—thought to be the first in the nation—is a don’t-miss experience. Tourgoers depart from the tiny watermen’s hamlet of Bayford on Virginia’s Eastern Shore, and paddle an easy 45 minutes along the pristine, protected shoreline of Nassawadox Creek to Church Creek before disembarking at Chatham Vineyards. The 20-acre waterfront farm makes a lovely setting for a picnic lunch. After sampling the winery’s half-dozen vintages, it’s back into the kayaks for a decidedly mellower trip home. Your Guide: Several certified eco-guides lead the tours out of SouthEast Expeditions’ Cape Charles, Virginia, locale. At Chatham Vineyards, the winemakers themselves, Jon and Mills Wehner, often do the meet-and-greet and chat up visitors about the vintages. Highlight: If you join a tour in spring or fall, you’ll paddle past a blue heron rookery on an island in the middle of Church Creek. All tours include a complimentary bottle of Chatham Vineyards wine. Details: Tours run spring through fall. $89 per person, which includes single or tandem kayak rental. 32218 Lankford Hwy., 757-695-4001

Skipjack Sails on the Rebecca T. Ruark (Tilghman Island)

The Tour: One of the best ways to experience the bay is the most traditional: aboard a working skipjack. The Rebecca T. Ruark, a National Historic Landmark and the oldest surviving skipjack on the bay, has been plying the Chesapeake since she was built in 1886. The two-hour tours on the Choptank River are as relaxing as they are educational: Captain Wade Murphy, a fourth-generation waterman, dispenses history and science lessons on bay ecology, as well as plenty of opinions on the challenges of earning a living from the sea. Your Guide: After six decades of working the water, Murphy and his boat have reached legendary status. During his tours, the captain shares plenty of personal stories from a lifetime spent on the bay, including the sad tale of when the Ruark sank during a storm in 1999. (She was raised and rehabbed soon after.) Highlight: If you’ve ever fancied yourself a waterman, this is an opportunity to prove your mettle: Captain Murphy lets landlubbers hoist the sails, steer, and sometimes work the dredge—all this and you don’t even have to wake up at the crack of dawn to do it. Details: The Ruark sails twice daily from the end of May through October. $30 per person. 21308 Phillips Rd., 410-886-2176