SeaDAN on the Chesapeake: Murphy’s Law, Crushes & 41 Years Together

It had been more than a month since Deb and I had given everyone an update from the Loop, and somehow those weeks had disappeared in a hurry.

As we sat aboard SeaDAN in St. Michaels, Maryland, looking back over everything that had happened since late August, one thing was obvious:

We had covered a lot of water.

We had explored the Chesapeake Bay, discovered some incredible little towns, made new friends, dodged thunderstorms, bounced through rough water, hit bottom, broke a few things, drank our share of Maryland Crushes, welcomed a new granddaughter into the world—and celebrated 41 years of marriage.

Not bad for a few weeks on the water.

And after all this time on the Great Loop, we’ve learned something else.

Murphy is apparently traveling with us.

Back in the Water—and Back on Plane

We left the Atlantic Yacht Basin around noon on August 24, finally beginning our journey north toward the Chesapeake.

Our first destination was the Hampton area, about a four-hour cruise away.

Naturally, we couldn’t just leave without a little delay.

We needed fuel and a pump-out before going through the Great Bridge Lock, and we missed the opening by about five minutes. That meant sitting around for another hour.

Then, right on cue, a huge barge showed up. Of course it did.

They wanted us in the lock with them, so in we went.

Eventually, though, we were back underway—and that’s when something happened that we’d been waiting a long time to see.

SeaDAN got back up on plane. Yay!

After having our transmissions and diesel engines worked on, this was the first real test. Before the repairs, we weren’t getting enough RPMs to lift this big beast out of the water.

This time, she did it. That was a great feeling.

Even better, when we checked the engine room later, everything looked exactly as it should. No leaks. No water in the fuel. Nothing alarming.

Warships, Submarines and a Lonely Anchorage

Heading north past Norfolk was spectacular.

Neither of us had traveled this far north by boat before, and cruising past the massive naval shipyards was something to see. Huge Navy ships, container ships and all kinds of marine traffic surrounded us.

That evening, we anchored in the Mill Creek/Phoebus area. It wasn’t exactly our favorite anchorage.

There was a busy bridge nearby, an underwater cable we had to watch for, and we were the only boat anchored there. Our navigation charts also showed a restricted area nearby, which didn’t exactly make us feel more comfortable.

Then we noticed something on Marine Traffic. A submarine was cruising nearby. Now that was cool.

Marine Traffic shows AIS information for vessels around you, so we could see where ships were coming from, where they were headed and how fast they were traveling.

Sitting alone at anchor while watching a submarine cruise past isn’t exactly something we did back home in Cincinnati.

“Going Faster Will Make It Smoother”

The next morning was windy, so we waited until around noon for conditions to settle before heading farther up the Chesapeake.

The water was still rolling. We had wind coming from the north and current coming from the south, producing a choppy two-foot sea.

That’s when I came up with one of my brilliant boating ideas. Maybe if we went faster, the ride would be smoother.

It wasn’t. Instead, we broke shit.

Our ceramic shark broke. A coffee mug went flying. Deb’s LEGO flowers crashed down and scattered into pieces. Going faster definitely didn’t solve the problem.

Then our Raymarine electronics started flickering on and off. Because apparently the broken shark and LEGO flowers weren’t enough.

Eventually I traced the problem to the power connections, cleaned everything up, and got the electronics working properly again.

While out shopping we found a sign that seemed to summarize life aboard SeaDAN perfectly:

“Murphy’s Law: Nothing is as easy as it looks. Everything takes longer than you expect. And anything that can go wrong will go wrong—at the worst possible moment.“

We probably should have bought two of them!

The Best Anchorage Ever

After about four hours of getting beaten around, we turned toward Deltaville and entered the Piankatank River.

Then we found Fishing Bay.

It was magnificent.

Deb immediately declared it the best anchorage we’d ever visited—which she tends to do whenever we find someplace beautiful.

But this time she had a pretty good argument.

The water was perfectly calm. Cute houses surrounded the cove. A couple of catamarans were anchored nearby.

And dolphins were playing in the water.

We gave Fishing Bay a 10 out of 10.

After the day we’d just had, sitting quietly at anchor while dolphins swam around SeaDAN was exactly what we needed.

North to the Solomons

The next morning we did something very unusual. We got moving early. Those who know us understand just how impressive that is.

By 8:30 a.m., we were underway toward Solomons, Maryland. It was sunny, about 78 degrees, with calm winds and smooth water.

In other words, a perfect cruising day.

Around noon, we crossed the Potomac River. Turning to port and following it upstream would eventually take you toward Washington, D.C.

But the Potomac demanded our attention.

One enormous cargo ship was heading south while another was approaching from behind us. We moved out of the channel and let the big boys have it.

Around 2:30 that afternoon, we entered Solomons and pulled into Spring Cove Marina. We immediately loved the place.

Katie, one of the dockhands, greeted us and helped with our lines. She ended up helping us throughout our stay. The marina had a large swimming pool, bar, private showers, picnic areas, bikes, a courtesy car, golf-cart shuttle service—and pump-outs right at the slips.

But the most important discovery came shortly afterward. We discovered the Maryland Crush.

Discovering the Crush

We dropped the dinghy and headed to the famous Tiki Bar. That’s where we were introduced to Crushes. Orange Crush. Grapefruit Crush. Key Lime Crush. Vodka, fresh juice, Sprite and whatever other magic they put in those things.

Deb was happy with the Crushes. I got a Jameson on the rocks. Everybody wins.

One of our favorite things about traveling is sitting at a bar and talking to the people around us. We’ve met some fascinating people that way.

At the Tiki Bar, we started talking to a couple and eventually discovered they were part owners. Naturally, we became friends.

The next night they invited us back and got us into a concert featuring the Amish Outlaws. We sat at their table and rocked out late into the night.

Just another quiet evening on the Great Loop.

History, Otters and a Lighthouse

We spent three nights in Solomons and managed to visit what felt like nearly every restaurant in town.

We also visited the Calvert Marine Museum and toured the Drum Point Lighthouse.

The museum had everything from paleontology exhibits to a Megalodon shark skeleton.

And otters. Live otters. They’d swim around their tank, come up to the glass and show off for everyone watching.

Eventually Sunday morning arrived and it was time to move again.

Our original plan was to stop in Deale. But the weather was beautiful. The water was calm. So I looked at Deb and suggested we keep going. Let’s go all the way to Annapolis.

I’m glad we did.

Welcome to Annapolis

The trip took about six hours.

Unfortunately, we’d forgotten one important detail. It was Sunday. And apparently every sailboat on the Chesapeake had decided to go sailing. They were everywhere.

Sailboats behave differently than powerboats, and when you’re surrounded by them, you really have to pay attention. They’re crossing in front of you, changing direction and seemingly appearing from everywhere.

Then, at exactly the wrong moment, our Raymarine electronics started acting up again. Murphy had returned.

We were entering the Severn River and trying to turn into Weems Creek. Boats were coming toward us. Boats were behind us.

For just a moment, I took my eyes off the depth. That was enough. Thunk. We touched bottom.Then the props hit again.

We managed to get through the shallow area and anchor safely, but it was an anxious few minutes.

Once settled, I put on the dive gear, went underneath SeaDAN and checked the props.

Thankfully, there was no damage.

Another lesson learned: When you’re navigating narrow channels with shallow water, you can’t afford to be distracted—even for a few seconds.

Ego Alley and the Naval Academy

The next morning we took the dinghy into downtown Annapolis. We cruised through the narrow waterway known as Ego Alley and tied up near the heart of historic Annapolis.

Cobblestone streets. Old buildings. Shops. Restaurants. It was exactly the kind of place we love exploring.

That afternoon we had scheduled a walking tour of the U.S. Naval Academy.

It was incredible.

Seeing the midshipmen in uniform, watching the formations and salutes, and experiencing all the tradition surrounding the Academy gave me goosebumps.

Our guide took us through the chapel, showed us the crypt of John Paul Jones and even showed us what the dormitory rooms look like.

The history of the Academy—and the list of people who have walked those halls—is extraordinary.

If you’re ever in Annapolis, put the Naval Academy on your list.

A Toast to Harry

We spent three days anchored near Annapolis.

The following day, we wandered through the boutiques and toured the Maryland State House.

The history there is incredible. Annapolis briefly served as the capital of the United States, and George Washington resigned his military commission there.

Afterward, we did what we often seem to do. We found an Irish pub. Galway Bay.

And then we found something even more special.

Harry’s Bar.

Harry was Deb’s father’s name. Whenever Deb and I find a Harry’s Bar somewhere in our travels, we stop. We go inside. We order a drink. And we toast Dad and share some memories. Since he was a midshipman himself, having served in the Navy during the Korean War, that’s exactly what we did in Annapolis.

Fuel or Thunderstorms?

Our next destination was Baltimore.

Unfortunately, thunderstorms were forecast to arrive around 2 p.m.

We also needed diesel.

So I gave Deb a choice. “Would you rather have fuel—or would you rather go through thunderstorms?” That didn’t take long for her. “Forget the fuel” says her (that’s pirate talk.)

Once underway, I realized the weather was approaching faster than I liked, so I put SeaDAN on plane and started running around 18 or 19 knots.

We were throwing a pretty impressive wake.

Then Deb’s phone rang. It was Lani and Jeff on the LaniKai, friends we’d met in Fort Pierce the previous year. They had been cruising nearby when they saw SeaDAN blasting along and throwing out a massive wake.

Apparently their first reaction was something along the lines of: “Look at this asshole!”

Then they realized it was us. SeaDAN. Busted. They caught up with us, and even better, they were heading to the same place we were—Anchorage Marina in Baltimore.

Then the Coast Guard came over Channel 16. Severe thunderstorms were approaching. Now we were racing the weather.

We pulled into our slip at approximately 12:47.

Around 1:00, the sky exploded. The storm hit with winds around 65 miles per hour.

We were very happy to be tied securely to a dock.

Fuel could wait.

A Very Important Trip Home

We spent time with Lonnie and Jeff, caught up over Mexican food and laughed about our adventures.

Then it was time to leave SeaDAN for a while.

We flew home to Cincinnati for one of the most important events of this entire journey.

On September 8, our granddaughter Juniper was born.

We spent a couple of weeks at home helping the kids, getting everyone settled and falling in love with our newest family member. Our first girl!!

Then, on September 28, it was time to return to SeaDAN.

The Loop was waiting.

Back to Baltimore

We arrived back in Baltimore early Monday morning. Naturally, the first thing we did was take naps. We were up at 4:00 to catch a 6:00 flight!

The next day, after some needed rest, we visited the National Aquarium.

It was impressive, with exhibits seemingly descending deeper and deeper into the water as you moved through the building. Sharks. Fish. Marine life everywhere.

There were dolphins, too. The aquarium no longer does traditional dolphin shows, but we were able to watch them swim and play.

We also explored Fells Point and—because apparently we are contractually obligated to find one in every city—found another Irish pub.

The James Joyce.

Fish and chips for Deb. Kilkenny’s for me. My favorite Irish nitro beer!

Baltimore has some wonderful areas, but like any big city, there are places where you need to stay aware of your surroundings.

We enjoyed our visit, but soon it was time to leave the western side of the Chesapeake and see what was waiting on the Eastern Shore.

Crossing the Bay

On October 1, we pulled away from Baltimore.

Even leaving the harbor turned into an experience.

A tugboat came up behind us, so we moved aside to let it pass. Then an enormous cargo ship approached from the opposite direction.

We watched the tug maneuver alongside the cargo ship and help guide it toward the inner harbor.

Watching those boats work together up close was fascinating.

Then we pointed SeaDAN east and headed across the Chesapeake toward Rock Hall, Maryland.

Duck Bucks and No Plans

Rock Hall turned out to be one of those places where having absolutely no plan produced one of our best days.

First, though, SeaDAN needed diesel. Rock Hall, Maryland: No Plans, Just Exploring

By the time we pulled into Rock Hall North Point Marina, one thing was at the top of our list: fuel.

SeaDAN had been running a little too close to empty for our comfort, so filling the tanks enough to give ourselves some breathing room felt pretty good. What didn’t feel quite as good was the price.

Diesel was $6.30 a gallon.

We put about 230 gallons into the tanks—and that only brought us up to roughly half full. We tried not to think too much about the bill. Sometimes boating is better when you don’t do the math.

With SeaDAN safely tied up at Rock Hall Landing Marina and enough fuel in the tanks to continue our Chesapeake adventure, it was time to do what we really enjoy.

Explore.

And Rock Hall turned out to be exactly our kind of place.

Duck Bucks and Our First Stop

Rock Hall Landing Marina was a great find. One of the fun little perks they offered was something called “Duck Bucks,”which gave marina guests discounts at some of the local restaurants and bars.

Naturally, we considered it our responsibility to put them to good use. Burp!

Our first stop was Waterman’s Crab House, right near the marina, where we kicked things off with a cocktail. From there, we wandered over to the Harbor Shack Bar & Grill, and before long, what had started as a simple afternoon of looking around had turned into one of those completely unplanned nights that we always seem to enjoy the most.

There was no itinerary. No reservations. No real plan at all.

Just two people wandering around Rock Hall to see what we could find.

The Youngest People in the Room

At some point, we heard music coming from an old building in a little strip mall. That was enough to get our attention.

We walked inside The Mainstay and discovered a live band playing what sounded like jazz. The place had a great atmosphere, although it didn’t take us long to notice something else.

We were probably the youngest people in the room.

By a long shot.

That didn’t bother us one bit.

We grabbed a couple of cocktails, found a place to sit and started enjoying the music. It was around seven o’clock, and we figured we’d stumbled onto the perfect place to spend part of the evening.

About thirty minutes later, the musicians started packing up.

“Wait. We just got here!”

Apparently, we’d missed one important detail. The music started at 5:00 and ended at 7:30. Old people… HA!

Even on a Thursday night. So much for that plan. Not that we really had one.

Wine, Backgammon, and a Little Humiliation

After getting politely booted out with the rest of the crowd, we headed across the street and discovered a wine bar.

It was one of those comfortable little places filled with couches, chairs and conversation areas that almost begged you to settle in for a while.

Then Chris spotted something in a back corner.

A coffee table. And a backgammon board. Game on.

We ordered a flight of red wines, sat down and started playing.

It did not go particularly well for Deb.

Chris proceeded to kick her butt so badly that she didn’t manage to get a single checker into her home board. Of course, Chris claims this was due entirely to his tremendous backgammon skills.

Deb remembers him rolling an awful lot of doubles.

Either way, it didn’t matter. We laughed, drank our wine and had a blast.

It was turning into another one of those nights where we just stumble from one place to another with absolutely no plan—and somehow those are often the best nights of all.

We call it exploring.

The Browns, Beer, and a Dark Ride Home

From the wine bar, our exploration eventually led us to Rock Hall Brewing Company, a little farther down the street.

One detail we probably should mention: We were doing all of this on bicycles.

At the brewery, we settled in to watch Thursday Night Football and cheer for the Cleveland Browns.

And they won!

That seemed like a perfectly good reason to celebrate a little longer. By the time we finally decided to head back to SeaDAN, it was around 10:30 at night.

That’s when we realized we had a small problem. No headlights. No helmets. And, naturally, we were wearing our usual dark clothes. Not exactly the smartest setup for a nighttime bicycle ride.

So we walked the bikes down the busier part of town. Once we reached the long, quiet road leading back toward the marina, we finally climbed aboard and started pedaling.

We rode right down the middle of the road. And amazingly, not one car came from either direction the entire way back.

Somebody was looking out for us that night.

We made it safely back to SeaDAN, climbed aboard and slept very well.

Although one of us felt considerably better than the other when it was time to get up the next morning. Damn Jamison!

We’ll leave it at that.

On to St. Michaels

The next morning, we continued south along the eastern side of the Chesapeake toward St. Michaels, Maryland.

We arrived on Friday, October 2, and almost immediately liked what we found.

St. Michaels is another beautiful little Chesapeake town filled with shops, restaurants, jewelry stores, bars, microbreweries and distilleries. It’s a little more polished—and maybe a little more expensive—than some of the towns we’d visited.

For our Cincinnati friends, think of it as having a bit of a Hyde Park feel.

Unfortunately, the weather didn’t exactly cooperate. We had two days of rain.

But we’ve learned something on this trip: bad weather doesn’t have to mean a bad day. So we kept exploring.

A Day at the Maritime Museum

One of our best stops was the Chesapeake Bay Maritime Museum, where we ended up spending a good part of the day.

We weren’t sure how long we’d stay when we walked in, but it turned out to be fascinating.

We learned about the boats that have worked these waters for generations, how they were built and how the Chesapeake’s oyster and crab industries shaped the lives of the people who lived here.

We climbed into the lighthouse and learned more about the region’s history, including its connections to the Underground Railroad and the stories of enslaved people who traveled through the area seeking freedom.

The museum also helped bring to life the story of Frederick Douglass, who was born on Maryland’s Eastern Shore.

Standing there, surrounded by the Chesapeake, made all of that history feel much closer than simply reading about it in a book.

But one of our favorite museum moments had nothing to do with an exhibit.

Near the water were tanks containing Chesapeake blue crabs. Two young boys were nearby with nets, happily catching crabs and helping stock the tanks.

Every once in a while, a crab would stubbornly grab onto the net and refuse to let go, leaving the boys shaking and bouncing the nets while a small crowd watched.

They were having an absolute ball.

And watching them was one of those simple little moments that made us smile.

The Bikes Have a Mind of Their Own

The next day, we climbed back on the bikes and found a beautiful trail that wound for about three miles through the woods.

It was quiet, peaceful and a great way to see a different side of St. Michaels.

Eventually, though, we started heading back toward town.

And that’s when we saw it.

A sign that said:

BEER.

Strangely enough, both bicycles immediately stopped.

We have no explanation for it.

Since the bikes clearly wanted to stop, we figured we shouldn’t argue. We pulled into the brewery and enjoyed a beer before continuing toward Talbot Street.

Once we reached the busier part of town, we mostly walked the bikes. Between the sidewalks, pedestrians and traffic, we figured that was probably the safer option. For the pedestrians!

We’d already pushed our luck enough in Rock Hall.

Celebrating Our Anniversary

That evening was especially meaningful because it was our anniversary.

After several days of bicycles, breweries, museums, rainstorms and spontaneous exploring, we cleaned ourselves up and headed to Limoncello, a wonderful little Italian restaurant in St. Michaels.

It was the perfect way to end the day—and a pretty good way to celebrate another year together.

Sitting there over dinner, we couldn’t help thinking about how much had already happened on this trip.

Some of the best memories weren’t things we’d planned weeks or months ahead.

They were the places we wandered into because we heard music.

The wine bar we found after getting kicked out of a jazz club at 7:30.

The backgammon game in a corner.

The beer sign that somehow stopped our bicycles.

The two boys wrestling blue crabs from their nets.

And the nighttime bike ride back to SeaDAN when the road, thankfully, belonged entirely to us.

Those are the moments we seem to remember.

South Again

Tomorrow morning, we’ll say goodbye to St. Michaels and continue south.

We’re heading back toward Solomons, but this time we’re planning to anchor instead of staying at a marina.

Our goal is to make it back to the Norfolk area by the middle of the month. From there, we’ll fly home for a couple of weeks, spend Halloween with family and friends, and then return to SeaDAN around the middle of November.

After that, we’ll point the bow south again and begin chasing warmer weather for the winter.

Where exactly will we end up? We’re not completely sure. And that’s becoming one of our favorite parts of this adventure.

For now, we’re enjoying the Chesapeake, discovering little towns we’d never really known before and learning that sometimes the best days are the ones when we wake up without much of a plan.

We’ll just keep exploring and see where SeaDAN takes us next.

— Chris & Deb