Back in college (the 70s), a bond was set for life with a few guys who were both fraternity brothers and roommates in a succession of apartments after we all moved out of the dorms. Our alma mater, Old Dominion University, is blessed to have the Chesapeake Bay as both a classroom and playground.  

Collectively this group has thousands of Bay miles and thousands of ICW miles under their belts. 

In those days, one of us had a sailboat, a venerable Cape Dory 25. I can’t tell you the number of classes we skipped to be out on the water—definitely playground!

I lived on a houseboat in Norfolk for a year or so post-graduation. So, the “boys” and I enjoyed a little extended boat time. But eventually the jobs, marriage, and kids took their rightful place in our lives. For a while, the pursuit of happiness did not include a boat.

In 1992 I pulled them back together for a “boys sail.” It was the first of what has become an annual, and sometimes more than annual, event.

Kevin Hoffman. What started out as "boys sails" eventually shifted to powerboat cruises.

We have cruised the Chesapeake on six different sailboats, owned or chartered for the purpose. About seven years ago, like so many sailors before me, I converted to power. In a succession of three powerboats, the boys and I have cruised the Bay and the ICW to south Florida and back.

My fraternity brothers/roommates turned crewmates are Dave Sampson, a retired high school teacher; Kevin Hoffman, a retired civil servant; and Skip Gibson, a retired consultant. Collectively they have thousands of Bay miles and thousands of ICW miles under their belts. Okay, yes, they also have a few thousand adult boat beverages under their belts, and it is starting to show.

In our 30 years of Bay and ICW cruising we have had some memorable and some wish we could forget experiences, all part of boating. 

In our 30 years of Bay and ICW cruising we have had some memorable moments.

One such memory was a leg from Norfolk to Reedville on my then-boat, an eight knot North Pacific trawler. We were pushing to get to Annapolis, so we headed out into the Bay under dubious conditions. We had a mixed sea with waves out of the north and remnant waves from the east. The result of this was what I would call the “washing machine” effect. 

Not far past Mobjack Bay, the inevitable mal de mer set in for two of us (who shall go unnamed). Two of us managed to keep breakfast down and navigate to our back-up destination of Reedville. As we turned towards Reedville, the motion got temporarily worse and one of the bilge alarms announced high water.  

With no available crew to look inside the engine room we just plowed on to calmer water. It seemed like forever but was likely only a few minutes. The entrance to Reedville was a blessing in more ways than one. The calm water had an immediate impact on the sea sickness sufferers. It also afforded me the opportunity to turn over the helm and look in the engine room where I found the bilge alarm was just a float switch stuck in the up position. 

These "boys sails" were certainly never dull. 

Another great memory, almost catastrophic but with a happy ending, was along the ICW. One of us (not me) was at the helm in a real “ditch” section of the Ditch. They call the ICW the Ditch for a reason as some sections are merely wide enough for two boats to pass, with high mud banks on the sides. 

When navigating the ditch sections, the autohelm is very handy. The helmsman can navigate a fairly straight line and follow the deeper water course by touching the autohelm buttons for one degree left or right turn.

Some autohelms are also set up for a 110-degree sailboat tack. This was the case on my trawler. The helmsman needs to hit both the one-degree and ten-degree buttons at the same time to tack.  

Yes, as fate would have it, an intentional one-degree shift left became a 110-degree command when both buttons were unintentionally hit. The hard left turn was abrupt at eight knots. I was in the galley making lunch. I set a land speed record scurrying up the steps to the pilothouse, reaching for the autohelm to go to manual steering, while slamming the boat in reverse. We narrowly escaped planting the bow in the mudbank side of that section of the ditch.

Left to right: Dave Sampson, Kevin Hoffman, Mike Pitchford, and Skip Gibson in Jupiter, FL. 

Fortunately for us we were relatively alone in the Ditch at that moment. With no other boats observing our strange maneuver, we backed away and restarted our true course while breathing a collective sigh of relief. The unintentional tack became known as the “fat finger move,” F2M for short. Not long thereafter, and to this day, the reference brings a smile to our collective faces. 

In 2022 we have one boys sail on the Bay under our belts and one to go. The boat will winter in south Florida, so an ICW delivery leg is scheduled for October. 

The recently completed first of the year boys sail started with a trip from Annapolis to Baltimore for an overnight downtown at the Inner Harbor Marina and an Orioles game. Cruising is now at 20 knots on my downeast style Back Cove 37, the third powerboat since converting from sail. We got to Baltimore in a couple of hours! The marina was great, but the O’s game was rained out. The rain, however, did not keep us from finding a great dinner in Federal Hill.

Our next stop was Georgetown, MD, which is 10 miles up the Sassafras River. I had not been there since my 30-something sons were young teens. Our chosen marina, Skipjack Cove, and Georgetown itself had not changed much in the intervening years. Everything looked the same except that I could not find the rope swing on the edge of the Sassafras, near the marina, that the kids played on 20 years earlier. Their pool however was a welcome relief on this hot August cruise (adults don’t look good on a rope swing anyway).    

Winsome Winn.

From Georgetown we headed to Deale and Herrington Harbour North. The marina is huge! Let me just observe that they nearly run out of alphabet naming the piers. You can get your daily 10,000 steps walking the marina grounds. Most importantly they had a pool!

This boys sail, like many of our cruises, featured a ballgame. In this particular itinerary we planned a second game, ending the cruise back in Annapolis so that we could drive to a Washington Nationals game on Saturday evening. The weather was finally a little cooler and this game was never threatened by rain. And the Nats won, a not so common occurrence for a struggling last place team.  

The final event of the cruise was our visit to Chick & Ruth’s Deli in Annapolis. Chick & Ruth’s is a more than 50-year-old Annapolis institution. It is a favorite of the legislators and staff in this capital city. The walls are lined with photos of notable guests and the menu items are named after legendary lawmakers.     

It was Sunday morning and our visits to Chick & Ruth’s are often a religious experience as one among us worships their breakfast potatoes. And so, worship (and overeat) we did! 

By Mike Pitchford