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Cruise Away on the Chesapeake Bay: Explore the main attractions of cruising

Apr 26, 2016 03:27PM ● By Ann Powell
We launch a three-part article series on the joys, tact, challenges, and whims of cruising Bay waters, navigating coves, and exploring the towns that dot the Chesapeake. Is the good life for you?

Story and photography by Ann Powell

Ah, the cruising life. Gently swinging on an anchor. Swimming off the stern. Nodding off to the rhythmic lap of water on the boat hull. Waking to the sounds of birds calling and workboats thrumming through the mist. Climbing above deck to begin a new day, the pungent smell of coffee brewing in the galley. This is the cruising life—it’s the Chesapeake Bay cruising life.

No question, the human soul needs to be outdoors and physically in touch with the world around us. You can get your earthly fix anywhere you choose—on a mountain, in a meadow, in a city park, in your garden, or just relaxing on a flat rock or an Adirondack chair. But if you’ve got the time and the nautical know-how, you’ll want to be on a boat on the Chesapeake Bay.

The Bay is beautiful viewed from the shore, but the world as seen from a boat is a whole new adventure. Boating takes many forms: fishing, paddling, river rafting, diving, sailing, and speed racing— but the most fulfilling just might be Chesapeake Bay cruising. The Bay has over three thousand miles of shoreline to visit, with around 48 rivers and hundreds of creeks, a lifetime of possibilities for a cruiser.


The Cruising Life

Chesapeake Bay cruising means using the boat as a kind of floating RV for overnight voyaging from place to place. Cruising really is a lot like camping, only a little cleaner—it’s great for anyone with a wanderlust and a desire to see the world from a new perspective. In the Bay’s most remote coves and crannies, you’ll see solo boaters, romantic couples, groups of friends, and families with small children, all overnight cruising on vessels of every size and persuasion.

Cruising offers an intense form of togetherness for family and friends. My own family has cruised for more than 30 years to many anchorages and marinas on the Bay, and every trip leads to unexpected adventures and plenty of quality family time.

We provision the boat with meals, bedding, swim gear, games, electronics, and everything else needed for a great vacation. After somehow stowing all this below deck and then circling back to the dock at least once to retrieve forgotten items, we’re underway, full steam ahead. There is no better feeling than heading out by boat to travel the Bay.

Voyages on First Light

Every sailboat and powerboat has its own personality and design for sleeping, cooking, and hanging out. We love our boat First Light, and she gets us wherever we want to go, but a multi-room mansion she is not. First Light is a Sabre 42 powerboat with passenger seating above deck near the helm. Below deck, the boat has two sleeping rooms called staterooms, each with a queen-sized bed called a berth.

The v-berth is in the forward stateroom, tucked in the boat’s v-shaped bow. Another stateroom with berth lies along the starboard side of the main living space, known as the main salon. The dining table banquette in the main salon converts to a third berth. That’s it. The boat sleeps six people max—unless someone is willing to sleep on the deck. As they say, “sleeps six, loves eight.” There is nowhere else to lay your head—those twin diesels in the engine room take up an awful lot of space. But somehow the tight fit never gets in the way of the fun.

Our four adult children grew up cruising on our Jeanneau 42 sailboat, Hurricane. The sailboat Hurricane had four “staterooms” with plenty of berths, and the kids loved our voyages on the Bay, including many two-to-ten day cruises with friends in the Sailing Club of the Chesapeake. We lived and played in close quarters, meshing our personalities and subtle quirks, as we learned about teamwork, tolerance, patience, and what it means to be a family.

But the day came when the kids became teenagers, as kids will do, and suddenly other things became far more important to them than long sailing trips. Social lives, soccer and basketball games, marching band tournaments, and more kept us on a short leash on the Bay. That’s why (dare I say it?) we’re now cruising on a powerboat.

1) Betsy Dunigan and George Dunigan cruising on Lightfoot. 2) Spinnaker flying on Corsair. Author’s husband, Eliot Powell, takes a “flight” while friends enjoy other aqua activities. 3) First Light at anchor


A Great Way to Have Fun

No one wanted to miss the most delightful parts of cruising—hanging on a hook in a quiet cove, rafting up with other boats and friends, and maybe taking the dinghy to a beach or the local town pier to explore. Staying out overnight on the Bay can range from grabbing a mooring in Spa Creek at Annapolis, to anchoring in an undeveloped nook on the pristine Little Choptank River, to taking a transient slip at a marina in Rock Hall.

There are several ways to secure a boat—there’s tying the boat to a permanently fixed mooring marked by a buoy in a harbor —or dropping an anchor to grab the mud on the creek bottom—or tying the boat to the pilings in a slip at a marina pier. Anywhere on the Bay, you can find like-minded folks mooring their boats, anchoring out, or overnighting at marinas. There’s a cruising group in nearly every community, marina, and yacht club, as well as many options for chartering a boat.

No place on the Chesapeake is too far to go if you have a few days, a nautical chart, and a depth sounder. We’ve travelled south to the Rappahannock River and north to the Chesapeake and Delaware Canal, as well as to many gorgeous creeks and friendly marinas in between.

Chesapeake winds, weather, tides, currents, water depth, and shifting shoals can be fickle and tricky. Running aground on a shoal can do damage to a skipper’s dignity and vessel, for sure. Any good skipper studies the rules of the road and the responsibilities of seamanship before heading out, and filing a float plan with contacts at home is a must.

1) John Roberts on Windemere


Rafting Up and Gunkholing

Anchoring out is a little more work for the skipper and crew, but the rewards include privacy and quiet, clear water for swimming, the chance to explore remote headwaters by dinghy or kayak, and sunrises and sunsets over beautiful coves. Some of the most serene anchorages lie in unfamiliar and difficult to navigate tributaries, and those are the “gunkholes” of the Chesapeake. But you don’t have to be a “gunkholer” to enjoy cruising.

Sometimes several boat captains looking to anchor out with friends choose to “raft up,” pulling alongside one another and tying their boats together using ropes (called lines) secured to metal cleats positioned along the boat deck. The procedure for rafting up is well-rehearsed with a seasoned crew. An anchor is set by the “mother ship,” and the raft then forms by lashing the vessels together one at a time and side by side. Fenders are placed between the boats to protect the hulls and rigging, just in case of rough water from boat wakes or bad weather.

It’s quite a production—our largest raft was a circle of more than 20 boats—but most rafts are maybe two-to-four boats on one hook. Maybe you’ve seen a raft of boats in a nearby cove and wondered how those folks know how to have all the fun.

When the skippers are satisfied that the raft is set in good form and the anchor will hold, kids and adults jump in to cool off, and soon the dinghies, paddleboards, and kayaks are launched. The skippers tinker happily with boat maintenance tasks, the appetizers appear from the galley, and families just…well, they just hang out. Visitors arrive by dinghy from other rafts, barbeque grills are mounted on the boat sterns, kids gather for board games while adults chat, and sometimes everyone dinghies to shore for group picnics.

It’s all about good, clean fun and friendship on the water. Try it sometime—you just might get hooked!

Adapted from the writer’s post “Family, Love, and Cruising the Chesapeake,” at, February 2015.

Read Part 2 Here: Small Boats on Big Boats

Read Part 3 Here: Four Days on the Bay