The Great Loop is a most unusual adventure of a lifetime.
You can start wherever you want. Go wherever you want. Take however long you need. Aboard any boat you choose.
You can bring the kids. Or not. Bring the dog. Or not. Hire a captain. Or not.
You can stop in the middle, take a break, and finish another time. Or start over and do the whole thing again. And again. Forever.
All while becoming part of a cruising community that grows by the hundreds each year as more and more boaters learn the joys of discovering America anew from the water—and making the experience whatever they want it to be.
Goals are key, especially if you don’t want to drive your wife nuts.
“In 2019, Tsali was starting to talk about retirement,” Jacque Bentley recalls. “I said, ‘You know, when you retire, you need a plan. If your plan is to come home and tell me what to do, you better find another one.’”
Tsali had sailed across the Atlantic, and he thought that might be fun to do again, but the idea scared Jacque. They were in their late 50s and had sailed on Lake Lanier in Georgia, near their Alabama home. Their Morgan 33 was a great boat, but when they started talking about the Great Loop, they realized having a mast was a bad idea, given all the bridges. So, they signed up to attend a rendezvous hosted by the America’s Great Loop Cruisers’ Association.
“They go over all the routes that you’d be doing on the Loop until the next rendezvous for the people who are in progress. For the people who are planning or thinking about it, there’s another track that talks about the basics of how to buy your boat, deal with the insurance, all of that,” Tsali says.
The Bentleys—both electrical engineers—brought pads and paper aboard 34 boats at the rendezvous, from Cutwaters to Flemings. They noted pros and cons, and talked to Loopers about their experiences. They decided a Mainship 400 was ideal, bought the 2005 Compass Rose in 2020, and set a course south in 2021 for the Gulf of Mexico.
Crossing at about 7 knots, they realized they had made the right choice. “Tsali and I were both sitting on the front of the boat, and he said: ‘Look at all the stars. That’s what it’s like when you’re sailing across the Atlantic,’” Jacque recalls. “And I said, ‘Good, we both got what we wanted out of this trip.’”
From Florida, they cruised up the East Coast, hooked a left through the Erie Canal, and explored the Thousand Islands before turning south for the Mississippi River and heading back home. It took them nine months. “That was way too quick, but our son called and said he was getting married, so we had to get home quicker,” Tsali says.
They’re now doing their second Loop, but slower. Florida seems wholly new. “It’s a totally different trip,” Jacque says. “We went up into Everglades City this time. We did go back to the Keys, but we skipped Miami and Fort Lauderdale, and we came up the western side to Fort Myers and then cut across Lake Okeechobee.”
The only real plan they have now, Tsali says, is to enjoy this time around even more than the first.
“On this second Loop, as soon as we get tied off, we go for a walk or a bike ride or something,” he says. “The last time, the first thing I always did was wash the boat. Now I say, ‘It can wait.’”
The Nebo App
Like most cruisers doing the Great Loop these days, Tsali and Jacque Bentley use the Nebo app. They can see where other Loopers are tying up, ask fellow Loopers about marina services and tourism opportunities, and keep a log of their route around the Loop.
Luck is how Ann Matwick describes the day she ran into a girlfriend in Atlanta, just one month after her husband, John, retired at 65 as an airline pilot.
“She said, ‘You won’t believe it, but my husband bought a trawler and we’re doing the Loop,’” Ann recalls. “I said, ‘What is a trawler?’” The friend showed her The Loopers Companion Guide by John Wright. “I came home and told John, ‘I think I found an adventure for us.’”
The Matwicks liked boating—on their 19-foot ski boat. “I thought, Well, OK…” John says. “Ann started doing some research, and she kept getting these phone calls from these guys, all these boat brokers.”
Ann, a therapist, realized that for sanity’s sake, she wanted an extra stateroom for stowage and an extra head for convenience. They went to Florida and looked at two-stateroom, two-head brokerage boats. The Kadey-Krogen 44 was the one.
The survey was in early 2021, during the pandemic, so John did all the repairs himself to satisfy the insurance company. Ann, meanwhile, got her six-pack captain’s license.
“John said in the airlines, one person would take off and do the landing, and the next leg of the trip, the other one would do the takeoff and the landing,” she explains. “I said, ‘Well, now I’m a captain, so how about we do that? I’ll take her off the dock, and when the day is ending, you’ll bring her in to the dock.’ We always say, ‘Hey captain, I have the lines all ready.’”
They set off in May 2021 and headed north for Annapolis, Maryland, to see their son at the Air Force Academy. They stayed on the Chesapeake Bay for a year, learning and fitting out the boat.
Then, in summer 2022, they were off. “We were different by then,” Ann says. “We say the Loop took us seven months to complete, but it was really one year and then seven months.”
Like most Loopers, they ventured counterclockwise. On the Mississippi River, they learned that navigating around barges can require a woman’s touch.
“Usually, when Ann made these radio calls, they were so nice,” John says. “When I would make the radio calls, they weren’t always that nice.”
Completing the Great Loop made them so happy that they’re now planning for the Down East Loop. “What you learn through it is amazing,” John says. “You almost can’t even describe it. You learn a lot about yourself. You learn a lot about each other and what you can do.”
Time is a finite resource. After 20 years in technology and software sales, Carson Diltz was ready for a change—and not just in his career. He enjoyed boating on Lake Michigan Time aboard a Sealine 42 Sedan Bridge with his wife, Allison, and their teenage daughters, Brooklyn and Reegan, but a cruise the family took during the pandemic left him thinking differently about time.
“The guy we bought the Sealine from, he took us out on Lake Huron, and Carson talked about how his dream was to do the Great Loop,” Allison recalls. “And he said they wanted to do it too, but his wife got cancer. So you need to just go and do it.”
Allison and the girls turned to Carson, he recalls: “They looked at me and said, ‘But we’re not doing it on the 42-foot Sealine.’”
The girls wanted their own rooms. Allison wanted a washer and dryer, and a bigger galley. That is why when they cast off in 2022 from Sturgeon Bay, Wisconsin, they were aboard their Carver 506, Crab Shack.
Admittedly, Carson says, it was a lot of boat for the Loop, with 5 feet of draft fully loaded. They hit bottom and required prop work three times along the way, but they could spread out, with the girls attending school remotely thanks to Starlink. It was a tough start, with the girls feeling bored and missing their friends. Few other Loopers had kids. Staying in marinas most nights did make it easier to walk their 2-year-old bichon mixes, Archie and Rosie.
Less than six months later, around the time they reached Florida, Carson had resigned from his job—and the warm blue water and sunshine in the Keys had helped to lift the gloom. Everyone finally felt like they were boating. The Bahamas was another big boost to their spirits. Reegan fed pancakes to the pigs at Big Major Cay. Allison gasped at the views. “It’s pretty amazing, especially in Bimini,” Allison says. “You look out at the water, and you think you must be in a fantasy.”
Seven weeks later, they were cruising up the Eastern Seaboard. By then, the girls had a new outlook. “I thought it was cool,” Brooklyn says. “Definitely not something you would see in a classroom at school.”
They were back in Wisconsin by summer 2023, in time for the girls’ next school year. Brooklyn is now eyeing Europe and the West Coast. Allison is thinking Canada. Carson is mulling the Down East Loop.
“It was an interesting choice for a sabbatical,” he says. “People say, ‘Oh, you took a yearlong vacation,’ and we correct them. We took a journey.”
That journey, admittedly, challenged them all in more ways than they expected. But in the end, Carson says: “It was worth it. Our family got closer.”
Online School
Carson says the teens’ schedules were a top priority: “The girls had to log in at certain times for their virtual school, so the first three months, we really tried to travel on Friday afternoons, Saturday and Sunday, and then stop and sit Monday through Thursday.”
Making the Midlife Leap
After the Loop, Carson chose to stay in the same industry, but with a smaller company: “Having the courage to walk away from a career and go do this was not easy or comfortable or even a safe decision, but it’s allowed me to come back to my career with a much better perspective. A job is a job, and it’s important, but there’s a lot more important things in life too.”
Two Adults, Two Teens and Two Dogs
Allison says having a bigger boat and staying ashore helped keep the family calm: “We were only on anchor seven of the 200-plus days, so we got to walk around a lot. We were never on top of each other. You see some of the boats people are doing the Loop on, and you think, How did they not kill each other? We had no injuries and no divorce, so that was good.”
Grit after a career-ending injury is usually an athlete’s story. Amy St. Germain, though, was a dentist. She was in her late 50s, not ready to retire but forced to by hand surgery.
Fate, she figured, was knocking. She’d already sailed the Intracoastal Waterway on her 28-footer. Now she would attempt her dream of cruising the Great Loop on her 49-foot steel-hull trawler, DeViking. “I had always planned to do this, but I figured this was the time,” she says.
DeViking also needed life-changing surgery. Built in 1986, it had rust—enough to require a jackhammer. Wiring was shot; bilge pumps and batteries too.
“We rebuilt the boat,” says Capt. Jeffrey Miller, who has been St. Germain’s skipper and cruising partner since 2021.
During the two-year rebuild, they added a crewmember, after finding him freezing and tied to a tree. Miller paid the owner of the boxer-pit bull mix $100 and welcomed Sancho aboard. The trio launched in April 2023 from the North Carolina shipyard, all of them finally free. They headed north toward the Chesapeake Bay and whatever else the Great Loop had in store.
“In Annapolis, it was graduation day, and we got to see the Blue Angels,” St. Germain says. “And in New York, we went to Katz’s Deli. We ordered mountains of pastrami.”
The Hudson River led them to the Erie Canal and, eventually, the beauty of Georgian Bay. They saw the Northern Lights, cruised Lake Michigan late enough to see the autumn leaves, and discovered the Benjamin Islands in Lake Huron. “That’s otherworldly,” St. Germain says. “It’s gorgeous. It has big rocks, these granite outcroppings, and they’re weirdly shaped. It feels like being on a different planet.”
They steered clear of crowds down the Mississippi River and across the Gulf of Mexico, stopped to eat Cajun food with St. Germain’s family in New Orleans, and leaned on Miller’s background as a sailboat racer in Florida.
“We got to be the committee boat for F-18 races in Sarasota Bay for a day,” he says. “We were blowing the horn, doing time trials. It was so cool.”
As of now, they’re in the Bahamas. For how long, they’re not sure, but it sure is fun playing dominoes with the locals and watching Sancho run on the beach.
“Everybody searches for freedom,” St. Germain says. “I think that’s what this gives you. It’s a chance to have the freedom to do whatever you want, whatever it is.”
Great Loop Navigation Notes
This book by US Coast Guard Capt. Alan Lloyd is the Bentleys’ go-to resource at the helm. They highlight each navigational mark as they pass it. They also have a binder filled with business cards. The first section is cards from other Loopers they meet, and the second is marinas they like so they can find them again or recommend them to other cruisers.
Aglca Rendezvous
The America’s Great Loop Cruisers’ Association holds two rendezvous each year. This autumn’s event will be October 21-24 at Joe Wheeler State Park in Rogersville, Alabama. Plans are for the same two tracks the Bentleys first encountered while starting to learn: one about the upcoming season’s Loop routes, and the other about the basics of the Loop.
