Best of the Bay Boating

Creative Director

I’m not from the Chesapeake. I come from the land-locked Midwest; Duluth was my “seaside town.” But I was fortunate enough to grow up with a lakefront cottage where I spent the summers driving outboards, pulling waterskiers, and sailing in one-design races on a tiny lake in Iowa. I loved the lakeside playground as a child but longed to someday be on a big body of water—a place where boats weren’t dodging each other, avoiding mishaps and collisions by zooming around in a tight circle. 

So the first time I stepped onto the cobblestones of Annapolis, with a view of the Chesapeake Bay from the top of Main Street (“Were there really towns like this in the U.S.?!”), I was moved to move there. My husband and I were in Annapolis to buy a boat—a sailboat, to live on. It was a harebrained idea, but as young newlyweds we didn’t have much to lose, or any idea of everything we were about to learn. Did I know that our Panda 38 would have fifteen pumps? Fifteen! Had I even heard of a pulsation dampener? Or an impeller? I thought sail trim, docking, and navigation were all you needed to know when you lived on a sailboat. I was totally wrong! 

After 33 years of boat ownership on the Chesapeake, I have come to know many people just like us who dove into buying a boat not knowing much about the mechanics of boats. But our Chesapeake community comes to the rescue. There are few places in the world where boaters have all the resources at their fingertips to learn every aspect of powerboating and sailing. From boat rental clubs—where you can get your sea legs before launching into a purchase—to diesel mechanics, electricians, riggers, and seamanship schools, our Bay is teeming with nautical experience. There is no easier place to learn the ropes (or lines) of boating than the Chesapeake Bay.

From Hoopers Island photo credit: Kate Fritzinger

There is also no better place for exploring and cruising. Our picturesque bay is shallow but soft and forgiving. The numerous anchorages are protected, peaceful, and usually have a good anchor hold. There is abundant waterfowl; fishing is top-notch. But it’s not all On Golden Pond. The summer squalls can come through with a fury, beat you up, and leave you with ripped sails and missing dinghies. Small craft need to heed the NOAA weather warnings; it can be life or death. The Chesapeake Bay classroom offers all boaters a well-rounded education.

Boat ownership does not come without its own exasperating set of challenges, however. There will be mechanical and electrical problems that make you curse the day you bought your boat. The cost of marine repairs is usually well out of your anticipated budget. The DIY fixes are in places you can barely fit into, let alone turn a socket wrench. But after a few years of fortitude you realize your knowledge of boating has grown exponentially. Every new trick you learn from your engine mechanic, your diver, your boat broker, has built up a boating knowledge you never thought you’d acquire. And docking your boat? Well, you’ve got that down like motor memory.

So don’t hesitate to lock into that dream of boat ownership. Be patient. Learn from all the Chesapeake boaters who are knowledgeable and helpful; there are as many of them out there as there are beautiful creeks and harbors to explore. 

Hampton Harbor


Annapolis, Md. and Hampton, Va.

Annapolis is known as “America’s Sailing Capital,” not just because of the year-round series of races for boats big and small sponsored by several different yacht clubs, but also because it happens to be the capital city of Maryland. Oh, then there are all the bars, too. And of course, it’s the home of the original in-water sailboat show that’s gathered sailors to the City Dock from all around the world every October for more than 50 years.

Hampton has much to offer sailors and powerboaters alike cruising in the southern Chesapeake Bay, from gracious yacht clubs to resort-like marinas and restaurants embracing Tidewater traditions. Summer is regatta season on the Hampton River, home to numerous sailing schools. Attractions include the Fort Monroe National Monument and the Old Point Comfort Lighthouse to the Virginia Air and Space Science Center. Hampton boasts a multitude of boat ramps and kayak launches that allow access to its many beaches and natural areas where wildlife abounds.

Herrington Harbour South


Herrington Harbours North and South, Anne Arundel County, MD

These two family-owned marinas on Herring Bay in southern Anne Arundel County earn kudos on multiple levels, from their manicured grounds to the country club amenities like swimming pools, saunas, formal and informal dining options, not to mention nearly 600 protected, deep-water slips with direct access to the open Chesapeake Bay. The onsite Yacht Center is considered one of the most comprehensive boat repair and maintenance facilities on the East Coast. 

Riverwalk Landing Piers, Yorktown, Va.

The Riverwalk Landing Piers provide docking for transient boaters close to all the town’s many restaurants and shops, outdoor concerts and festivals. The concrete floating piers provide 1,200 linear feet of dockage. A second pier located behind the Riverwalk Restaurant provides additional docking. Mooring balls are also available. Amenities include electrical, water, and sewer pump-out, plus a private shower and restroom. Readers appreciate the facility’s “Clean Marina” status.



Leo Wardrup Memorial, Cape Charles, Va.

For nearly 20 years, the Leo Wardrup Memorial Cape Charles Cup has provided a weekend-long “cruising event for serious racers and a racing event for serious cruisers.” Sponsored by the Broad Bay Sailing Association, the regatta is named in honor of veteran sailor Leo Wardrup, who passed away in 2014. Rolling starts of various classes launch in mid-August from Norfolk’s Little Creek Marina and sail about 16 miles across the Chesapeake Bay to Cape Charles on the southern tip of Virginia’s Eastern Shore. 


Triple Crown of Charity Sailing, Annapolis, Md.

The Triple Crown of Charity Sailing, sponsored by Weems and Plath, was created in 2018 to recognize the top sailor and fundraiser for The CRAB Cup, The Leukemia Cup, and The Hospice Cup races. The skipper with best score in the three races and highest fundraising wins a “keeper trophy,” while the permanent trophy is on display at the Market House in downtown Annapolis. Proceeds benefit Hospice of the Chesapeake, The Leukemia & Lymphoma Society, and the Chesapeake Region Accessible Boating program.


Best Place for Kayakers to See Bald Eagles: Blackwater National Wildlife Refuge Cambridge, Md.

With some 28,000 acres of forestland, saltmarsh and shallow water, Blackwater National Wildlife Refuge accommodates one of the East Coast’s largest breeding populations of bald eagles, a species seen year-round in this bird-filled Dorchester County sanctuary. Two launch sites, three scenic water trails, and several outfitters offering rentals and guided tours make Blackwater a welcoming haven for paddlers as well.
– Marty Legrand

The esteemed editors of CBM have sent me on another fool’s errand to pin down the “Best of the Bay.” Lucky for them I am just the fool to try, with this caveat: There are too many great fishing products made in Chesapeake region to pick just one. 

Best Bay-Made Fishing Lures: G-Eye Jig

Years back, when Capt. Lonnie Johnson first introduced his G-Eye Jigs, I asked him why he decided to make his own jig heads. He replied that since he is super-focused on realistic action and quality, the best way to accomplish those goals is do it himself. What sets G-Eye Jigs apart from other jigs are the oversized, prism eyes, which help incite game fish to strike. G-Eye Jigs are hand-poured using quality materials, and each jig is finished with a topcoat of UV paint for increased underwater visibility. He also uses superior hooks, so when you do hook into that big fish, it stays hooked.

Best Handmade Custom Fishing Rods: JLS Custom Rods

As a fishing outfitter and part-time guide, I’ve learned a few things about quality rods. A relative newcomer to the custom rod-building game, JLS Rods will make you a rod to catch fish, whether it’s panfish, freshwater trout, red drum or cobia. Their rods are in the hands of hundreds of hardcore anglers and professional guides. Heavily focused on using high-quality components and craftsmanship, perhaps it is their willingness to do unique customization that sets them apart, at least in the eyes of their customers. So if you’re looking for a high-quality, custom rod, JLS Custom Rods should fit that bill.

– Chris D. Dollar

Best Watermen’s Heritage Tours: Rappahannock Roundstern Tappahannock, Va. 

Join Capt. Richard Moncure and Mate Nate Parker aboard one of two vintage 38′ roundstern deadrise workboats for fishing, natural history, and eagle tours around the spectacular Fones Cliffs; exploration of the Captain John Smith Chesapeake National Historic Trail; and hands-on oyster tours.

John Page Williams

Best Long-Distance Boat Race: Great Chesapeake Bay Schooner Race

Every October around Columbus Day weekend, schooners from all around the world gather in Baltimore to take part in this iconic overnight race to Norfolk for fun, camaraderie, and a grand pig-and-oyster roast at the end. The fleet parades around Baltimore’s Inner Harbor and down the Patapsco for the spectacular race start off of Annapolis. Proceeds support the environmental and educational programs of outstanding Chesapeake Bay organizations.
– Jefferson Holland

Best Place to Get Hard-to-find Items for Your Boat: H.W. Drummonds, Eastern Shore of Va.

Catering to watermen since 1959, H.W. Drummonds is a family-owned business that carries a wide variety of hard-to-find parts and accessories for boats, engines, and trailers. Drummonds is especially strong on all kinds of lubricants, lights and terminals, bottom paints, zincs, cleaning supplies, fuel tanks and treatments, and electronics like depth finders, radars and GPS units. The knowledgeable staff will take time to understand your needs, and if they don’t have it in-house or at one of their four locations (plus three gas stations), they can usually get it in one day. 
– Robert Gustafson

Best Place to Watch the Sunrise and Sunset: St. Michaels, Md., and Annapolis, Md.

My favorite places to watch sunrise or sunset are far removed from quiet anchorages. I like to greet the sun or end the day in a marina or on a mooring ball in the company of nearby kindred spirits. In St. Michaels harbor, watching the orange and gold of the sun as it creeps up through the masts never gets old (and I’ve got the pictures to prove it). For sunsets, Annapolis Harbor is my choice. Just before the sun goes down, it colors the tops of the waves with gold. Along with the State Housedome in the distance and the sounds of “Retreat” from the Naval Academy, sunset doesn’t get any better.,

– Niambi Davis

Antique & Classic Boat Festival, St. Michaels, Md.

It’s a Father’s Day weekend tradition for the family to head over to the Chesapeake Bay Maritime Museum and watch Dad drool over all the beautifully bright-finished mahogany runabouts, vintage race boats, and elegant wooden motor yachts crafted by the likes of Chris-Craft, Trumpy, Gar Wood, and Lyman, on display in the water and ashore at the Antique & Classic Boat Festival. Enthusiasts from all around the Bay area bring their lovingly restored floating treasures to the festival. Produced by the Chesapeake Bay Chapter of the Antique & Classic Boat Society, this June marks the event’s 34th year. 

If you’re looking for a project, you’ll find it among the dozens of boats for sale in the “Field of Dreams.” The Nautical Flea Market has a wide variety boating accessories and equipment. The Arts at Navy Point features some of the best-known maritime artists and craftspeople from Canada to Florida. But the best fun is watching the fleet of 9-foot-long Jersey Skiffs hydroplaning across the Miles River.
– Jefferson Holland

Best Historic Water Trail: Capt. John Smith Chesapeake National Historic Trail

At 1,800 miles around the tidal waters of the Chesapeake, Capt. Smith’s is the National Park Service’s only all-water National Historic Trail. It follows the explorations of Captain John Smith and his crews from April 1607 to October 1609. During that time, he took extensive notes that he incorporated into the first accurate map of the Chesapeake Bay and its large tidal rivers, which he followed all the way to their heads of navigation. Publication of the map in 1612 opened the Bay to English colonization in the 17th century. Explore it today by any vessels from paddlecraft to trawlers, using the free online guide at
-John Page Williams

Best Little-visited Waterfront Park: Magothy Bay Natural Area Preserve, Townsend, Va.

For solitude in beautiful Eastern Shore surroundings, the Magothy Bay Natural Area Preserve is a hidden gem. A few miles north of Cape Charles, Magothy Bay is a 445-acre state park that is little visited and a little hard to find! Its two trails include a loop through migratory songbird habitat, but the crown jewel is the 2.2-mile walk through the coastal pine forest and along a causeway overlooking the salt marsh along Magothy Bay and the barrier islands beyond. Look for wading birds foraging for shellfish, and diamondback terrapins and marsh hens enjoying the mud flats.
– Robert Gustafson

Best Ferry: Tangier Ferry, Tangier and Onancock, Va.

There’s been a lot of talk of ferries lately, from suggestions of a ferry crossing to alleviate Bay Bridge backups to electric ferries in downtown Annapolis. But at the foot of Bay, ferries are a way of life for the folks on Tangier Island. The Joyce Marie II, a 36-foot, deadrise-style boat captained by Tangier native Mark Crockett, does twice-daily roundtrips between Onancock and Tangier from May until October, ferrying locals and their groceries, visitors and their suitcases, and whoever else needs the hour-long passage. Tickets are available on a first-come, first-served basis at Tangier Harbor (departing 7:30 a.m. and 3:30 p.m.) and Onancock Harbor (departing 10 a.m. and 5 p.m.), so get there early—or better yet give them a call to reserve in advance. Keeping it old-school, payment is by cash or check only—no credit cards.
-Susan Moynihan