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Here’s How to Cruise the Entire Bay in a Runabout (One Loop at a Time)

Editor’s Note: We receive several stories per year from Chesapeake Bay Magazine readers who want to share their special boating memories from time spent cruising the Bay. While we can’t publish them all, we love this concept from three-decade CBM reader David Avedesian, a former 100 Ton Master who has cruised all over the mid-Atlantic. We can’t wait to copy some of his cruises!

Avedesian makes a strong case for seeing almost any nook of the Bay with a trailerable/shallow draft boat. He shares the close-to-shore routes and tricks that allowed him to see much of the Chesapeake’s tributaries without voyaging across large swaths of Bay. Get inspired by his trips: Launch your own small boat and see the Bay.

In my years of boating, I have owned two trailerable boats: a 16-foot Evinrude tri-hulled ski boat and a 23-foot recreational runabout (a restored 1977 Formula 233 we call Black Beauty). With these two boats, I have cruised the waters and tributaries of the Chesapeake Bay in a manner that traditional (larger) cruising boats could only dream about doing. And I did it with 2-4 people on board.

Black Beauty tied up on Mobjack Bay during a boat trip.

Since 1994, my family, friends, and I have been gathering for Boat Trip Weekends (about 48 hours of fun, door to door). These special weekends began after my grandmother’s funeral. A survivor of the Armenian Genocide of the Ottoman Empire, she passed away at 84 years old. The grandchildren expressed a common sentiment: Why do we only get together for funerals and weddings?

I said, “I can fix that!” and began organizing an annual boating weekend. We have leveraged the advantages of a trailerable/shallow-draft boat to see the wonder of the Chesapeake Bay’s natural riches. The two big advantages of small boats? You can tow them anywhere and you can navigate the skinniest, most protected water.

Because a small boat is not intended for use on rough water, the key to my trips is to avoid large stretches of potentially choppy open water. With the 16′ ski boat, we limited our trips to rivers and canals. The ski boat drew a mere 6″ of water with the 125hp Yahama outboard engine tilted up. In any other boat, we might still be waiting for the tide to change.

Planning can be fun when working within small-boat parameters, and each trip has a “personality” all its own. On a cruise from Lewes, Del. to Ocean City via Assawoman Creek, we were able to run the creek in both directions. On the first leg south, the tide and water depth allowed us to power all the way through. On the return trip north, not so much. At one point, I had to get out and push until the incoming tide could get us moving. We still speak about the trip often, and would not have enjoyed it as much without the added adventure of those moments waiting for the tide.

On our small boats, we experienced great hospitality in some of the Bay’s most far-off communities. On Smith Island, I tasted the best cream of crab soup I’ve ever had at Ruke’s Seafood Deck. (Sadly, Ruke’s closed for good in 2015.) When we got there looking for crab soup and learned the restaurant had recently closed, someone ran to get the women that had made Ruke’s soup. They offered to make a full pot of cream of crab soup for our gang. We enjoyed it knowing the soup was the last of its kind. It was made in genuine goodwill to strangers from the sea.

The late, great home of my favorite cream of crab soup.

On a Rappahannock River cruise to Urbanna, some friends and I enjoyed cigars and Crown Royal Manhattans at a nice restaurant in town. We kept the stories and the Manhattans flowing for hours. When the restaurant owner informed us he had run out of Crown Royal, we paid a runner to pick up more Crown from the next town over. On my next boat trip to Urbanna, the marina dock manager said, “Oh, so you are the guys who drank Urbanna dry of Crown Royal! Welcome back.”

The story goes that we ran Urbanna dry of Crown Royal. Photo: Virginia Water Trails

Along with some forays within New York and New Jersey waters, here is a baker’s dozen of Bay-region weekend cruises that we have completed in our small boats:

  1. Lewes, DE, to Lewes/Rehoboth Canal to Assawoman Creek/Canal to Fenwick,
    DE, to Ocean City to Lewes, DE (inside passage)
  2. Chincoteague to Cape Charles to Chincoteague
  3. Crisfield to Smith Island to Tangier Island to Pocomoke River to Snow Hill to
    Crisfield
  4. Norfolk to the Great Dismal Swamp, to Elizabeth City, NC to Coinjock, NC to
    Norfolk
  5. Cambridge to Blackwater Wildlife Refuge to Nanticoke River to
    Seaford, DE
  6. Cambridge to Wicomico River to Whitehaven to Salisbury to
    Cambridge
  7. Cambridge to Choptank River to Tuckahoe Creek to Greensboro, MD
  8. Colonial Beach to White Oak Landing, VA, to Mattaponi River to York River to
    Mobjack Bay to North River to White Oak Landing, VA
  9. Jordan Point, VA, to James River to Chickahominy River to River’s Rest to Chickahominy Lock/Reservoir to Jordan Point, VA
  10. Fredericksburg, VA to Urbanna to Fredericksburg
  11. Havre De Grace to Chesapeake City to Salem, NJ to Havre De Grace
  12. Gravelly Point, VA, to Mount Vernon, VA to Colonial Beach to St. Mary’s City
    to Shark Island to Mattawoman Creek to Gravelly Point
  13. Gravelly Point to the Potomac River to St Mary’s City to Gravelly Point.

(We have also seen the historic sights in Baltimore and Annapolis.)

On our Chesapeake City trip, we stayed at the historic Ship Watch Inn, and you can see why.

No matter the destination, we plan our weekend itinerary with roughly the same formula. It’s the journey itself that varies widely. Here’s how we travel well for 48 hours without a galley or proper cabin on board:

A leisurely lunch aboard at Lake Drummond, Feeder Ditch for the Great Dismal Swamp National Wildlife Refuge

Friday: The crew trailers the boat 3-4 hours from home to the first night’s stay, usually at a bed and breakfast (airbnbs work just as well).

Saturday: We launch the boat at a public boat ramp, leaving our vehicle and trailer overnight. Loaded with gear and food, we cruise towards Saturday night’s destination and stop somewhere to eat lunch on board. We make this lunch a real event, provisioning our small boat with things like bagels with smoked salmon and all the trimmings, Italian homemade Sopressata with cheese and olives, some traditional Armenian delicacies, brie with hot pepper bacon jam, dark chocolate covered bacon, and the list goes on. We spend 2+ hours enjoying the feast and get back underway. Upon arrival to our destination town, we check into an B&B and step out for dinner. Sometimes there are Manhattans.

Sunday: After breakfast, we board the boat and retrace Saturday’s float plan, with a stop for another relaxing lunch. Back at the boat ramp, we reload the boat on the trailer and travel 3-4 hours back home with stories to tell.

The serene view at North River Plantation, where we made friends with the staff and the chef prepared us a seven-course dinner.

Because we tackle a different destination each year, the adventure lies in exploring new waters. I find that everyone has fun for six months talking about last year’s trip and then we have fun talking up the new boat trip for six months in advance.

Note: When planning an adventure in a small boat, it’s especially important to take safety precautions. The captain is responsible for assessing the weather, water depths, tides and sea conditions for the safety of their vessel and for the boating skills of the crew.