Chesapeake boaters Nancy Merrill Sullivan and Jason Sullivan are in the midst of completing America’s Great Loop, a 6000-mile voyage that takes boaters around the eastern half of the United States and into Canada. When we connected with Jason and Nancy, they were cruising the Bahamas. “Sun, sand, clear blue water in February—who wouldn’t want to do that?” says Nancy.

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While cruising America's Great Loop, Jason and Nancy passed through 108 locks.

The crew and vessel

Annapolitans Jason and Nancy Sullivan, with their cavalier King Charles spaniel, Radar, are rounding the Great Loop aboard their 2023 Summit 54 Time & Tide. Nancy grew up sailing and boating on the Severn River and with her parents enjoyed many sailing adventures in the Caribbean and the Mediterranean. Jason sailed when he was in his teens and fished using skiffs in his ’20s but didn’t start cruising until he met Nancy. 

During the last 13 years the couple has owned several boats, starting with a Grady White 23, and progressing to a Sealine C330, a Prestige 460, and their current vessel, Time & Tide, which they purchased for their Great Loop adventure. The motoryacht has large windows, a sun pad on the bow, roomy staterooms, and a washer and dryer, making it both well-appointed and comfortable for an extended trip.

The route

Jason and Nancy are traveling the Loop counterclockwise. After taking delivery of their boat in Stuart, FL, in 2023, they completed a two-week shakedown cruise in the Florida Keys before motoring to their home slip in Annapolis, where they spent the next couple of months outfitting her for the Loop. 

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Jason and Nancy Sullivan are rounding the Great Loop aboard their 2023 Summit 54 Time & Tide.

They slipped the lines on May 30, with their then-22-year-old daughter aboard for the first week’s passage to New York City. The plan was to complete the Loop in a year’s time, taking a few side trips along the way.

Among their excursions off the main route, the couple has explored a bit of Lake Superior, cruised the Bahamas, and traveled up the “amazingly scenic” Tennessee River to Chattanooga. Like most Loopers making their way to the Gulf of Mexico, they chose to avoid heavy barge traffic on the Mississippi River by exiting the Tennessee to the Tennessee-Tombigbee Waterway, which also flows to the Gulf of Mexico. Not only is it a shorter route, but the waterway also offers more services for recreational vessels. 

Navigating an unusual year

“In most years about 150 boats do the Great Loop, but 2023-24 has been very unusual,” says Nancy. “More than 300 boats are doing the Loop. The number is probably so large because of restrictions to travel during Covid.”

On top of that, the first three locks south of Chicago were rebuilt during the summer of 2023, blocking all southbound traffic from the Great Lakes—both commercial and recreational—from June 1 to October 1.

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Radar poses before the White Cliffs of Epes, which stretch along the banks of the Tombigbee River in Alabama.  

Jason says, “Kim Russo at America’s Great Loop Cruisers’ Association (AGLCA) did a great job getting all the south-bound loopers organized into 16-boat flotillas. The biggest challenge was that the marinas south of Chicago only had slips for about 15-20 transient boats, and you can’t anchor on the Illinois River without blocking barge traffic. Having 50 boats go through in one day would have overwhelmed the few available facilities.”

Jason says, “The ALGCA negotiated with the Army Corps of Engineers, and the Corps reserved one lock-through for 16 recreational boats per day. Knowing that they would get us through was a big deal because commercial vessels always have priority on the inland waterways.”

Nancy adds, “Most of the Loopers joined a flotilla since being part of a group was easier and safer. Even with the flotillas, we had to wait two to three hours (sometimes circling and sometimes anchored) above locks. Our flotilla was number six, due to leave on October 6, but the Army Corps of Engineers was not quite finished rebuilding the second of the three locks we would pass through. They asked all the flotillas to wait an additional five days. Our group was to stage in Joliet, IL, but for us it would have been a long day to get there, so along with about seven other members of our flotilla we chose to stay instead at a marina that was about a third of the way to Joliet, which ended up working out well for us.”

A magnificent mix

Nancy says, “Some Loopers connect with a group of boats that they meet early on and travel together all the way around. That’s not us. What often happens is that we’ll be with a group of boats for three or four days, and when they’re ready to leave a location, we want to stay another day or two. So, we will stay and pick up another group. We’ve met so many wonderful people this way. One time in Tennessee we were one boat in a group of four, and by chance three us were from the Annapolis area: the Magothy, Severn, and South Rivers!”

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Exploring a castle in the Thousand Islands, which straddle the US-Canada border in the Saint Lawrence River.

Jason adds, “Stopping in small towns we’ve met some of the nicest, most generous, and down-to-earth people. It’s not uncommon for a liveaboard we meet in a marina to give us a ride to do an errand. One time, a small business owner where we were shopping even lent her car to us to drive 45 minutes to a veterinarian!”

About the other Loopers, Nancy says, “We’ve met four or five couples doing the Loop who did not have any previous boating experience. At first, we thought that seemed a little dangerous, but with some basic training, some real-time training, and by making careful decisions, they seem to be having a great time. We have also met lots of very experienced boating couples that have been cruising for years and others who have sold their houses and everything in them and now call their boats home. Some Loopers are retired. Others work remotely part or full time. It’s quite a magnificent mix of people!”

Home and family

As Nancy states, some Loopers rent or sell their “dirt home” while living aboard their “boat home.” Others go back to land for months at a time and complete the Loop over several years. The Sullivans return home occasionally. They have friends using their house while they are gone. In August they stopped in Annapolis for 48 hours on their way to a wedding, and Nancy came home for a week in October when Time & Tide was in Chicago. About the time that this issue of PropTalk hits the docks, the pair will be home again for a two-week stay. 

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Time & Tide in the torquoise blue waters of the Bahamas.

Jason and Nancy have made it a point to include friends and family in the adventure. In New York City they visited Nancy’s cousin. In Mackinaw City, MI, they visited Nancy’s friend Lisa Borre, who has a cottage in the area. Lisa happens to be a former longtime contributor to SpinSheet and connected us to Nancy and Jason. Nancy’s sister joined them for a few days on the Tennessee River. 

For the holidays, the couple shared Thanksgiving with one of Nancy’s childhood friends who lives in Oxford, MS. For Christmas they met all four generations of Jason’s family in Clearwater, FL, but not without a little last-minute rearranging. Situated in Carrabelle, FL, prepared to cross the Gulf of Mexico to Clearwater, they waited for a weather window. Finally, with no weather window in sight and the family flying in to meet them, Nancy and Jason ended up renting a car and driving to Clearwater, securing a rental property for the rest of the family, driving back to Carrabelle for the boat, and making an overnight Gulf crossing to rendezvous for the holiday gathering! 

Before leaving Florida, they slipped in another family visit, spending time in Marco Island with more of Jason’s family. When we spoke, our hospitable Loopers were in the Bahamas awaiting a few of Nancy’s friends to join them. 

Memorable places

Nancy and Jason agree that the Georgian Bay in Canada was probably their favorite spot if they had to choose one, but other locales stand out because of their unexpected beauty. They found the shoreline along the Tennessee river to be spectacular. The river rolls through the forest of the Tennessee hills with 100-foot bluffs known as the Tennessee Grand Canyon. On Lake Michigan, both were amazed by the enormous sand dunes on the east side of the lake, which is dotted by beautiful beaches and quaint towns. “They make the Ocean City beaches look small,” says Nancy. “Now we know why people from home travel all the way to Michigan to vacation there every year!”

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The Georgian Bay in Canada was one of Nancy and Jason's favorite spots.

Advice to those considering the Great Loop:

  • Don’t sit on the idea for 10 years or you may not get to go. You don’t need to start with lots of navigation, mechanical, or boating experience. 
  • The saying goes that the most dangerous thing to have on the Loop is a schedule. That is because it forces you to take chances you wouldn’t otherwise take. We’ve found that usually when we make plans, the plans end up making things more difficult.
  • We did 108 locks, and locks are more work than you’d expect. They’re not difficult, but it can be stressful and mentally fatiguing. 
  • We thought doing the Loop as a married couple would feel similar to taking a two- to three-week cruise, only longer. It’s actually a lot more work. It’s not an extended vacation. We are ‘working’ from 7 a.m. to 8:30 p.m. most days. 
  • Each section has its own set of wonders and set of anxieties. You’re constantly planning ahead, and since you don’t know what you don’t know, you need alternative routes and anchorages. 
  • Headphones really are marriage savers. As soon as one spouse starts raising their voice, the other does too. Shouting turns into yelling and feelings get hurt. Keeping your tone of voice low makes a world of difference. We actually have a pillow that says, “Sorry for what I said while we were docking the boat!”
  • Use the Nebo app to connect with other Loopers. Almost all of them have it. We help each other, track and text one another, make plans to meet for evening docktails, and share all kinds of information. Communicating with other Loopers is a good way to learn things like the best way to enter a harbor or where to find local spots that aren’t in the cruising guides.

Learn more about cruising the Loop at the America’s Great Loop Cruisers Association website,

For more on Great Loop cruising, check out our article Chesapeake Bay Boaters Complete America's Great Loop about Dave and Sonia Astle in their Ranger Tug R43 CB.