The Old Men and the Bay

Some adventures begin earlier than others but 35 million years ago has to be an outlier. That was about the time an exploding meteor smacked into the earth and formed a crater that became the Chesapeake Bay. Water, and its tendency to find the path of least resistance, had a role. Millions of years later, the Susquehanna River carved a 400-foot-deep canyon as it flowed from the Appalachian Mountains to the Atlantic Ocean. Ice ages, glaciers and rising sea levels played their parts, but this is not really a story about geology or climate.

It is much simpler than that, but that still does not make it simple as compared, for example, to a multi flavor order at Starbucks. It is about four guys who have progressed pretty far through their lives and their desire to spend four mid-May days together on a 47-foot boat called Reindeer sailing from Annapolis, Maryland to Norfolk, Virginia.

Our leader was 76-year-old Tony Parker, with whom I was joined in education for eight years at St. Paul’s and Harvard. Like me he has had a variety of careers and avocations, all of which contributed to making him interesting. A little like the forces that contributed to the creation of the Chesapeake Bay.

He has been a lawyer and an entrepreneur but his current company, Parkertide (note the nautical theme), provides contract labor to the federal government. He was also the multi-term treasurer of the Republican National Committee, which, shockingly, given the amount of money for which the person in that role is responsible, is a volunteer position. Worse, it is a volunteer position to which you must be elected, hence the additional burden of running for office. To his great credit, he stood down when the GOP embarked on its present course.

As in all matters related to sailing, Tony played two key roles. First, he owned the boat and second, he wrote the checks. Some in that position are admonished to “stay out of the way and keep the checkbook dry,” but not Tony. He began sailing as a child in Maine, where his father owned a boat yard, coached sailing at the Naval Academy, competed on America’s cup challengers, formed a yacht club at his bay side house to challenge for the America’s Cup, and competed at the world level in various classes.

The second participant was the comparably aged, Mike Howard, who only shared four years of education with us at St. Paul’s before going on to a distinguished rowing career at the University of Pennsylvania. He too has had a variety of careers in banking and, recently, he has led an effort to restore a Revolutionary War cemetery in his hometown of Fairfield, Connecticut.

Mike is high on the go-to list of good guy participants in golf trips as well as all manner of activities that draw men together in their “post-competitive” years. He has a background in sailing and knows his way around a boat, but not at Tony’s level.

I was the third, but readers of this blog know quite enough about me. The only thing you don’t know that might be at all relevant is that I know nearly nothing about sailing. But for a few years as a Navy officer, during which I was responsible for the seamanship aspects of my two destroyers, the “nearly nothing” would be “absolutely nothing.”

And that leads us to the fourth person. If Mike or I had fallen over the side, life on board could have continued, but, if Tony had fallen over the side, life as we knew it would have ended precipitously. (By the way, did you know that a high percentage of drowning victims recovered from sailboat accidents are found with their flies down? Pause. Reflect.)

A significant qualification of the fourth person must be that he could replace the skipper if needed. Ross Dierdorff, 67, is a Senior Analyst at the FDIC. He lives in Annapolis and has sailed with Tony for about five decades. During the summers, the Naval Academy hosts promising teenage sailors nominated by their yacht clubs for a few weeks of training, and, while coaching the Naval Academy sailing team in the early 1970s, Tony met Ross during such a training camp. They have sailed together in many offshore races including Annapolis to Newport and the Bermuda race.

You might be curious about how Tony came to be a sailing instructor at the Naval Academy. For that answer, we turn back more than 50 years. Both Tony and I graduated from college in 1968 and both of us were in Navy ROTC. On the day before graduation, we were commissioned as ensigns.

Tony was offered the Naval Academy sailing instructor job right out of college, where he had been a distinguished member of the sailing team, but he thought he would prefer to have the real experience of being a junior officer aboard a ship, so he turned it down.

About 18 months later, when that tour of duty was completed, he was offered the next “career enhancing” opportunity. Detailers are the people in the Navy who match officers with jobs. In “detailer speak” career enhancing tends to mean some manner of dreadful.

The job on offer was to be a forward air controller in Vietnam, which meant you called in airstrikes pretty much on top of your head. Between the airstrikes and the surrounding enemy, the life expectancy of a forward air controller was comparable to that of a mayfly.

Curiously, when faced with that career enhancing option, Tony re-opened the question of the sailing instructor role and thus did it come to pass.

There is a fifth character in this story whose name is Reindeer. Our boat was built and owned by Newbold Smith, a Naval Academy graduate a generation older than all of us. He wanted to sail it into challenging places, and, on at least one occasion, it went to the Arctic. As Newbold grew older, Tony took on more and more responsibilities when they sailed together and, eventually, he bought the boat.

Tony also owns a boat called a J24 and named Bangor Packet in honor of Tony’s roots. It is a “trailer-able” keelboat that is designed for sailors who want to cruise, day sail, race against other J24s, or compete in handicap events. It can go offshore. Given its name, it is perhaps not surprising that it is 24 feet long, or just about 1/2 the length of Reindeer.

I was curious about the ratio of time spent working on a boat to the time spent sailing it. By Tony’s estimate, a J24 requires one hour of work for every 24 hours of sailing, while the figures for Reindeer are the reverse — 24 hours of work per hour of sailing.

Now you have the cast for the four-day trip from Annapolis, Maryland to Norfolk, Virginia, well except for the cook, Claire Parker, who did not make an in-person appearance during the voyage. We stayed at Claire’s and Tony’s house (yes, the putative yacht club) the night before we left, and she reappeared at the end for a Cruising Club of America weekend, but the excellence of her culinary efforts, to say nothing of the detailed direction giving, were appreciated on a daily, if not hourly, basis.

Mike and I arrived from Connecticut and Washington, respectively, the night before departure and we joined Tony and Claire for dinner at a famous seafood bar in Annapolis. Much catching up, but little that was adventure related. Tony gave each of us a tour of the Annapolis area – me before dinner and Mike the next morning as we waited for the breakfast place to open.

A key aspect of the tour was the house the Parkers are building on a point of land between the bay itself and a more sheltered Lake Ogleton behind it. The lake will be the new home of Reindeer and Bangor Packet. The house will also have room for various Naval Academy midshipmen who are part of a sponsorship program in which Tony and Claire are participating. There is a windowless room of significant size in the cellar that will house the array of sails and other gear that do not reside on the boats themselves. The selection of the site itself required much attention to the depth of the lake to assure that Reindeer would not run aground at its mooring. Bangor Packet and a smaller power boat will live on lifts at the end of the newly built dock. I am confident there are a few in our mid 70s cohort who are embarking on such elaborate plans.

At midmorning, we arrived at the boat yard where Reindeer was tied up, and we stowed our gear. Mike and I were aft in the “pit,” a space Claire refuses to enter because of the amount of stuff stored in there. Likely, there is a better word than stuff, but that would require knowing the contents of countless nylon bags. Since none of the nylon bags interfered with my bunk, I never asked.

Tony has a way of dealing with the safety tour that makes you want to pay attention to the location of fire extinguishers, radios, life preservers, safety harnesses and so forth. Human resources and compliance departments throughout the land would do well to hone their presentation skills under his guidance. There is a fine line between stressing the importance of safety at sea and sounding pedantic. If you have spent time on the ocean, as I had on destroyers, you know that you are no match for what the sea can do to you, and a destroyer is seven times bigger than Reindeer.

A trusty boat yard mechanic appeared for a minor engine repair. Here, it might be instructive to reflect on the role of cell phones. The dock to which we were tied was easily in cell phone range, but we would never get out of cell phone range during our four days on the water. It made me wonder what sailors did before cell phones with trusty boatyard mechanics on speed dial.

Ross then made his first appearance and we all introduced ourselves. This was timely because another problem arose relating to one of the sails. Jibs now wind themselves around a stay that runs from the bow of the boat to the top of the mast. They look like very long cocoons when they are tightly furled, but it is useful to know which way they spool around the stay so you can coil the correct lines around the correct winches. For some reason, seemingly related to winter storage, we didn’t. Solution: easy. FaceTime the manufacturer of the furling device, point the phone into the machinery and get his advice. Probably, pretty much what Magellan would have done.

Just before departure is probably the moment to mention that the wind was blowing from north to south, which was propitious because we too would be going from north to south for the next four days. It was less propitious that the wind was blowing 20 knots, which was close to the least it would blow for the entire trip.

Two experts, one amateur and a buffoon with the wind blowing 20. The leadership was self-critical of the crispness of the departure; so it is with sailors. But we did depart, stowed the fenders, and motored out into the harbor. Then the jib was unfurled, thanks to the wisdom of the guy on the other end of the FaceTime call, and the excellent owner’s manual direction reading of the boys in charge. (Take note, ladies.) Reindeer took off like a jack rabbit under jib power alone. We never would see the mainsail.

My Navy experience did not include tomato, mozzarella, and basil on ciabatta bread for lunch, so I judged that considerable progress has been made on nautical culinary practices over the last 50 years. After lunch we replaced the jib with the spinnaker and spent the afternoon going south at about six knots.

Thanks to our exploding meteor 35 million years ago, there is a lot going on in the Chesapeake Bay that can influence the progress of a 47-foot sailboat. It had rained like mad in the week before the trip, and the rivers that empty into the bay were full. Essentially, the bay was overflowing with fast running water that was at cross purposes with the tide and current.

If things are going well on a sailing trip, there is a good deal of sitting in the sun, contemplating the day, and chatting with your shipmates. Though most of the stories that get recounted are filled with heroism and high adventure, more often, things seem to be going smoothly and you are telling stories to one another.

There are two significant differences between fables and sea stories. First, fables begin “once upon a time,” while sea stories begin “this is no shit.” Second, fables are far more likely to be true. The major categories of sea stories include mishaps in which the storyteller saves the day, and people whom the storyteller disliked spending all their time and effort trying to make themselves look good.

In these conversations, of which there were many during our four days together, I also learned that there is a difference between a good sailor and a good shipmate. A good sailor is helpful around the boat and reliable in times of stress. Almost certainly, he is experienced. Unfortunately, the stress can have a tendency to — and how shall I say this gently –- diminish interpersonal skills. Good shipmates don’t allow their interpersonal skills to falter, and they can often be nice people to have around. Having no hope in the sailor category, I took a dead aim on shipmate as, by then, I was quite certain I wanted to be invited back.

The afternoon continued without incident, and we anchored near Solomon’s Island at the mouth of the Patuxent River. After dinner, there was a repair to be made. Remember the 24 to 1 rule. We had been sailing for almost 6 hours so there should have been 144 hours of work to do. Tony reduced that number by one or two when he went up the mast in a bosun’s chair to untangle two lines that had been misaligned over the winter.

A conversation between dinner, launching Tony up the mast and bedtime was about the political frustration of four people with different life experiences, all of whom would self-characterize as moderates and all of whom dislike what passes for governance today. Four good listeners with a willingness to learn make for good shipmates. Also, some pretty good ideas.

At 8 PM, I relied on my years of Navy training to lower the flag, an activity that was to become my major on-board responsibility.

If you go to bed just after eight and sleep well despite being housed in the pit, you tend to wake up early and there was plenty of time for coffee before my major task of the day — raising the flag. It was blowing like hell and our destination was Saint Leonard’s Creek, which leads into the Rappahannock River and where we would learn about the war of 1812, mostly from Wikipedia on our phones.

Many of America’s 18th and 19th century wars were fought right where we were. The American Revolution came to an end at Yorktown, our day three destination, the War of 1812 was fought up and down the Chesapeake Bay, and the Civil War was largely fought not many miles inland from our anchorage.

By mid-morning when we took off, the wind had increased and again it was jib only, but Reindeer was going like mad. The first challenge was to avoid a bombing range (the blue circle on the GPS screen), which definitely seemed like a good idea.

Once we were clear of that, I was allowed to steer for a while and I discovered that what appears easy in the hands of an experienced sailor is, in fact, quite difficult. The wind pushes the boat one way, and the waves push it another. I was aiming for a specific point in the distance, but each wave would point the bow in a different direction, and I would try to compensate. This left a wake that looked like a snake, and that is the sign of an inexperienced helmsman.

By then, it was blowing 30 knots and Tony went below and returned with four safety harnesses. He told the rookies how to wear them and where to attach them, and there was not the slightest resistance to following his instructions.

About then, he said, “if I had known it was going to be like this, we would not have come.” Our speed had increased to a steady nine or 10 knots with frequent bursts to 13 or 14. That would not feel fast to a cyclist, but it feels really fast on a sailboat.

We could not quite get into Saint Leonard’s Creek because it was too shallow, and it was interesting to read that the same problem was experienced in the war of 1812.

According to the National Park Service,

“During the summer of 1814, the British navy tried to flush out and destroy the U.S. Chesapeake Flotilla—a rag-tag assembly of armed boats and barges.

British warships blockaded the mouth of the Patuxent River after the Chesapeake Flotilla and Royal Navy skirmished off Cedar Point on June 1, 1814. The flotilla escaped up the Patuxent following the skirmish and sought safety in St. Leonard Creek, four miles upriver.

The British pursued, and the largest naval engagement in Maryland waters – as well as some of the fiercest fighting of the war– occurred where St. Leonard Creek meets the Patuxent River.

After three days, the hard-fighting Chesapeake Flotilla had almost bested a vastly superior English force. On June 11, the British pulled a stranded and damaged schooner off a sand bar and began repairs.”

We tried one anchorage but, given the strong wind, considered it unsafe, so we set sail again, rounded a point and re-anchored in the Rappahannock River where the dinner conversation shifted to stories of St. Paul’s and Gilman, the schools we had attended. At 8 PM, the flag was lowered without incident.

Next up was the sail to Yorktown, where the wars changed from 1812 to the Revolution. Again, it was blowing hard, but for some reason, the harnesses were not in use. Instead of anchoring at Yorktown, we tied up to a dock near our only neighbor.

We were directed to come in one way but the combination of wind, tide, and current lead to a last-minute reversal of direction to avoid calamity. Another reason to have experienced sailors on your team.

Even amateur historians know that Yorktown is where Lord Cornwallis had decided to establish Winter quarters in 1781 and he hoped 1782. The battle of Yorktown took place in October 1781, and, given the outcome there would be no 1782 in the Revolutionary War. It involved astonishing planning in an era of extremely low speed communication.

Events that were planned for October were conceived in the winter or spring before. Yet the French Navy arrived to seal up Chesapeake Bay at the same time George Washington’s army arrived from the north. They did not appear to have been much real fighting at Yorktown. Instead, Cornwallis absorbed his untenable situation and more or less said, “OK, who gets my sword?”

We toured what there was to see by Segway, ably guided by a female high school senior who was her NROTC Battalion Commander. She is going to William & Mary, where she will study economics. If you need someone to come and work for you in about 2027, keep her in mind.

The last day was foggy and rainy but still blowing hard. We sailed from Yorktown to Norfolk passing the Navy base and seeing how different ships look today than they did 50 years ago. As the crews have gotten smaller, the capabilities of the ships have grown immeasurably greater.

During our time together, I was greatly struck by the progress of boys to men and how the dynamics change. Perhaps it was the inspiration of the Segway guide, who made me wonder, yet again, how any boys can get into college, when the 18-year-old girls are so much more capable.

One of our conversations related to Tony’s 50th birthday, which turned into a roast. That would never have happened at his 75th birthday because his friends would have mellowed, and they would have toasted the many good things about him rather than teasing him about his foibles.

Mike and I were to be replaced by Chef Claire when we docked and, when she arrived, she asked Tony, “well how was it?”

“Fucking miserable,” he replied.

It is an unusual sport when that is a good thing.

In a more recent conversation, he told me that, upon reflection, he thought it was one of the best sailing trips ever.

32 Responses to “The Old Men and the Bay”

John Austin Murphy, June 12, 2022 at 9:31 am said:

No matter what mishap may befall you, stay with the boat.


Haven Pell, June 12, 2022 at 9:50 am said:

With the possible exception of getting hit in the firing range, but that did not come to pass.


Allan Keene, June 12, 2022 at 9:45 am said:

Great story Haven..Epic!
For all of us in the bottom of the 8th a wonderful tale…


Haven Pell, June 12, 2022 at 9:51 am said:

Thank you Allan, keep moving keep playing.


Haven Pell, June 12, 2022 at 10:17 am said:

It is just a bigger Buffalo River.


Steve Park, June 12, 2022 at 10:41 am said:

Steve Park, Thanks for sharing. So glad to hear Reindeer is in good shape and cruising. I had the pleasure of knowing Newbold Smith and several of his sailing buddies as members of Racquet Club of Philadelphia. Reindeer’s trip to the arctic circle and back is well told by Newbold in a book he wrote about the adventure in 1980, “Down Denmark Strait”. Great fun!!


Haven Pell, June 12, 2022 at 5:01 pm said:

Thank you Steve, I am glad you liked the story. It is a lovely boat


David Irons, June 12, 2022 at 11:07 am said:

Hey there, Haven, Tony, Mike — and Ross Dierdorff,
Thanks for the voyage log. It all sounds like a fine four days of sailing deep into America’s past.
With mild degrees of envy as I contemplate a summer with less sailing than the past 15 or so, as my right knee whines on about growing and as yet unscheduled preference for titanium and ceramic.
Cheers, – David


Haven Pell, June 12, 2022 at 4:49 pm said:

Schedule it. It is a game changer.


Jimmy Weekes, June 12, 2022 at 11:49 am said:

A great tale. As you well know, my father loved sailing more than any other activity. He even employed a Pell on some of his winning races. I agree about the speed on a sailboat. When Game Cock was heeled to the rails it felt like the speed of sound. That and riding a horse at full gallop are the fastest I have ever my mind. Jib only? Yikes. My cousin Bucky, Brad’s younger brother taught sailing at the Naval Academy for a while. The rumor was that he lost his job by beating the admiral in charge in a race.

Remember, I have seen your ship handling skills at first hand. When my oiler refueled you in rough weather your tin can held her line beautifully. As for me, with my sailing skills, I would have been your unpaid underling on this trip.

Great read.


Haven Pell, June 12, 2022 at 4:52 pm said:

Thanks Jimmy, great reminder about my father and yours. Game Cock brings back memories as does the refueling. I really did like the seamanship part of the Navy.


james walton, June 12, 2022 at 12:12 pm said:

Rum, sodomy, and the lash; there’s never a bad day spent at sea!

Great tale, hope you got some sunshine too


Haven Pell, June 12, 2022 at 4:53 pm said:

Thank you James, as you saw, you provided one of the lines in the story.


Walter Deane, June 12, 2022 at 1:12 pm said:

Fantastic post! Well done!


Bill Gordon, June 12, 2022 at 1:33 pm said:

Well done Haven. Your vivid description of your experience only increases my jealousy.

Is there an on line course or a print instruction manual available that, upon completion, would increase my odds for a future invitation? I could handle the flag, contribute to the nightly conversations and even pay for the shore time dinners! Is that enough?

Please advise. Thanks for the fun read.


Haven Pell, June 12, 2022 at 4:55 pm said:

Bill, I am pretty sure “I know a guy.” I will work on it.


Jack Garrity, June 12, 2022 at 4:28 pm said:

Haven and Tony,
Glad to hear of your adventures on the Chesapeake.
Keep Sailing.


Haven Pell, June 12, 2022 at 4:55 pm said:

Thanks Jack, as you could tell, it was fun


Chuck Coggeshall, June 12, 2022 at 9:34 pm said:

Beautifully written sea/bay saga Haven. I have seen Captain Parker ascend the mast in a bosun’s chair before, but he was in his early 20s then! At 76 years old, in the medical world, we would consider that malpractice! But the boy obviously loves to do it. Heck of a trip!


Haven Pell, June 13, 2022 at 7:13 am said:

Indeed it was. Capt. Parker was a terrific leader and host.


MG Davies, June 12, 2022 at 10:20 pm said:

Haven, Tony, Mike + Ross Dierdorff : Loved your log of the latest Battle of the Chesapeake.
I hope Tony only goes up the mast at anchor these days.
Glad to see Haven summon his inner Arleigh Burke working his way up from JG to Flag officer.


Haven Pell, June 13, 2022 at 7:20 am said:

Thanks Mike, glad you liked the story. And yes, we were at anchor.


Dick Sonderegger, June 13, 2022 at 12:54 am said:


What a wonderful article! Your writing was always good, but it has improved many fold over the years.

I’m so jealous — for the writing, of course, but mainly for being part of your four-day adventure.

Good On Ya!


Haven Pell, June 13, 2022 at 7:14 am said:

Thank you Dick, at least some can be attributed to a compelling topic.


Dick Friend, June 13, 2022 at 3:38 am said:

After World Masters court tennis in Fontainebleau & Bordeaux last month, I accepted an invitation to a 4-day regatta on the Med, sailing out of Leucate. At least you didn’t spend the first day “feeding the fish”. Hardly the recovery from the rigours of world-competitive tennis!


Haven Pell, June 13, 2022 at 7:15 am said:

Dick, I hope both went well and that we will see you in Washington in November.


Montague Demment, June 13, 2022 at 8:31 am said:

Impressive story. Having done some of these trips, you capture the essence that makes each one unique and memorable. Well done.


Haven Pell, June 13, 2022 at 11:20 am said:

Thank you Tag. You would have been far more useful on board than I was.


Conn Nugent, June 13, 2022 at 7:56 pm said:

Thanks for this, Haven. Good tales and keen observations. Let’s have a drink sometime and talk about Yorktown.


Haven Pell, June 13, 2022 at 8:30 pm said:

Thanks for the compliments, Conn. Sounds like a plan.


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