The Great Loop—Full of History and Fun

Bill Andrews completed the Loop in 2020. He loves the history of the cities and towns along the route of the Great Loop, and the journey tells a great deal of the story of America, especially its early days. Bill shares his experiences of personal enjoyment, historical perspectives, and offers practical advice for those considering tackling the Loop. We’ve summarized the discussion within this article.

What are the geographical parameters of the Great Loop?

Bill: The Great Loop is a 6,000-mile journey including the East Coast of the United States, the Great Lakes, the Mississippi River system, the Gulf of Mexico, and Florida. It consists of travel through mountains, rivers, and locks. It is a neat way to see a significant portion of the country.

What motivated you to want to complete the Great Loop?

Bill: My wife and I are global travelers, always looking for another adventure. Being from Oregon, I grew up boating there and in the surrounding states like Washington, California, Nevada, and Arizona. Due to volcanoes and climate change, many places where I boated as a younger person no longer exist.

We traveled to the East Coast but did not feel that exploring by car quite captured the spirit of the East Coast. Since many of the cities are navigable by water, we decided to skip the traffic and do some real exploring.

What sort of history does the Loop have?

Bill: The Great Loop route covers about four hundred years of history because Saint Augustine, Florida, is the first city in North America. Much farther north is Plymouth, Massachusetts, where the colonies were first formed in the 1600s. In between, places to visit include Revolutionary and Civil War sites, the Great Lakes, and a chance to see firsthand how the industrialization of America unfolded. I even discovered a piece of my own history when I located relatives who lived in Plymouth approximately twenty years after the Mayflower arrived.

What kind of boat is needed to complete the Great Loop?

Bill: After a year and a half of searching, we bought a boat on the larger end, a fifty-five-foot power catamaran, because we wanted to bring family and friends along. We bought it based on the overall dimensions that would fit under bridges.

It was built by Victor Lipscomb from Washington, North Carolina, who worked with the famous sailboat designer, Malcolm Tennant. The boat came equipped with a fully enclosed upper deck and three staterooms. It was designed to go offshore for months at a time, cruising along at eight knots at around three nautical miles to a gallon of diesel with a range of about 1,200 miles.

As comfortable as it was, we rarely anchored out. We opted to tie up in a marina instead. The length was fine, but we did have trouble a few times due to the width of the boat, which was wider than most service lifts, especially in the northeast, where smaller seasonal boats are common.

For those looking to purchase a boat, I would recommend one that is easy to work on but has enough room for comfort, like a thirty-foot boat that can sleep four people. Some people even traverse the Great Loop route on a twenty-foot boat. A lot depends on how many people you plan to travel with you.

How did you tackle the trip all at once, or in segments?

Bill: For us, breaking the trip into segments made sense because we did not live on the boat. Since we brought friends, we scheduled two to three weeks at a time and traveled about five hundred miles per trip.

Afterward, our guests would fly home, and we would rent a one-way car rental that allowed us to see sights farther inland that we would not have been able to see, only traveling by boat.

In rural Virginia, we saw James Madison’s plantation and the room where the Bill of Rights was written. In Pennsylvania, we saw Washington’s crossing, where he crossed the river during the Revolutionary War. Being from the West Coast, I felt there were so many things to see during our trip because the East Coast has such a long and interesting history.

When we were ready for our next segment of the Great Loop, we returned to the marina, where we parked the boat and continued our journey.

The marinas we picked had enough infrastructure to support leaving our boat with no issues, even during the two hurricanes when we docked it there.

Did you have to pull your boat out during the winter months?

Bill: Yes, we traveled the Great Loop over two years, took a side trip to Maine, and stored it in Portland, Maine, for the winter. They have heated boat storage where I could go work on it and have a tasty lobster while there. For eight bucks, you can buy a lobster at the grocery store, where they will cook it for you so that you can bring it back to your boat.

What are the most meaningful and interesting places you experienced during your Great Loop journey?

Bill: I tried to narrow my list, but there are probably fifty to sixty truly notable sites. I started the Loop in Florida with the history of the 1500 Spanish settlements. Next was the Kennedy Space Center and its infamous trip to the moon. Farther up, you get into the Civil War sites and battlefields.

In Washington D.C., we took a side trip up the Potomac River and tied up at the Capital Yacht Club, where we docked bow to bow with Senator Manchin’s boat. It was pretty cool sitting there having a drink while looking at the Washington Monument. In Baltimore, the Star-Spangled Banner was written by Francis Scott Key, who the British captured on a boat. The city puts up a buoy where that boat was anchored.

From there, travel up through New York. We stopped at Staten Island at a wonderful marina. We then went on to City Island in Queens for some great seafood. Looking across the water at Hart Island, you can see where over a million people from NYC have been buried. After that, a trip to Cape Cod, then Plymouth, and then to Boston, which is incredible by boat. There we spent four or five days in Constitutional Marina. It was so cool to sit on the back of our boat, looking out at the USS Constitution only a hundred yards away.

From there, keep going up to Maine, where you can stop at Kennebunk. Portland, Maine, is also a wonderful place to see. North of there are small towns with art galleries. Finally, you end up in Bar Harbor, Maine. There is also Southwest Harbor. The whole island is a National Park that offers free bus rides around the island.

Inland from there is more of the country’s industrial history, like Detroit. It is also worth stopping in Alpena, Michigan; you can visit Shipwreck Museum. Another place is Mackinac Island, Michigan, and one of our favorite places on the west side was Charlevoix, Michigan. We did get stuck there for five days due to weather. There were waves as high as twenty feet because the water is so deep. It turned out that boating on the Great Lakes was the most challenging part of the trip because those waves are like ocean swells.

When traveling down the tricky Mississippi River, you must read about Tom Sawyer in the Adventures of Huckleberry Finn. However, the infrastructure there is less developed due to the flooding that occurs. Further down, you can stop at Beardstown, Illinois. Beardstown is where Abraham Lincoln did the Farmer’s Almanac trial two years before becoming President of the United States.

If you go up the Ohio River and down the Tennessee-Tombigbee Waterway through to Kentucky Lake, it is a hundred miles long and is a gorgeous lake. Stop at Camden, Tennessee, where Patsy Cline’s plane crashed. Camden has the only freshwater pearl farm in America.

Down in the northern part of Florida is Steinhatchee; some call it a drinking town with a fishing problem. In St. Petersburg, you can tie your boat up in town and visit twenty art museums.

What advice do you have for those interested in completing the Loop?

Bill: First and foremost, do it. The best advice is to plan and learn about boat operation and boat maintenance. We met boaters who never owned a boat, recently bought one, and decided to take this trip.

They ended up stuck due to maintenance issues and some minor accidents. Think about the boat ride the way you would a car ride. Bring along what you need when you cannot stop. Plan where you are going to go and what you want to do.