We Completed the Loop!
- onaboatsailing
- Mar 19
- 4 min read

CHICAGO — St. John’s graduate Greg Scannell was taking groups of people on sailing cruises out on Lake Michigan this past week, once again glued to the water and wind that he and his fiancee Cait Larson love. What their customers might not know is that this is no ordinary couple of salts or casual seafarers. The duo breezed into town on July 9, just having completed the Great Loop — a 6,000-mile waterway journey that takes mariners from the Great Lakes to the Gulf of Mexico via inland rivers, across the Gulf and around Florida, up the Atlantic coast to Long Island Sound, then up the Hudson River, through the Erie Canal, and then on a winding route through lakes Ontario, Erie, Huron, and Michigan back to the starting point, in this case, Chicago.
Their aim was to return here earlier in July so they could start taking people sailing and scheduling sailing classes.
As it turned out, the sailing outings commenced the day after their odyssey of 254 days ended.
“It wasn’t the ideal plan,” Scannell said, alluding to a delay they incurred while moored in the Michigan port of Rogers City on the Lake Huron side, while waiting on parts needed to repair an engine issue. They also encountered an expected holdup as they waited for foul weather to clear in Frankfort on Michigan’s northwest coastline. “The ninth was the earliest we could get back. Lucky for us, it all worked out despite being completely exhausted and not having much time to celebrate our accomplishment.”
The feat included negotiating 63 sets of locks, 53 lift bridges, and seven groundings and two tows. There was also a side trip to the Bahamas while the couple spent the winter months portion of their journey in warmer climes. The pair completed the Great Loop healthy and unscathed but also loaded down with stories from their more than eight months on the water — enough time for that to become normal.
“It has been a whirlwind getting back to life on land,” Scannell said. “Going into the trip we thought it would be a momentous crescendo of crossing our wake and completing the loop. In reality, it was just another day in the life of being on the water. We found a routine and rhythm to being transient, it became normalized.”
Things were far from normal at the October start of the trip since on Day 2 they had a harrowing experience in the set of locks at Brandon Road, just south of Joliet on the Des Plaines River. They entered the locks and were placed directly behind a tow vessel that was pushing nine barges.
“When the tow started to leave, it cranked up their huge engine and we were thrown off the lock wall and were spinning around,” Larson said. “We were screaming and just trying to hold on. It was probably the most scared we have ever been on the boat.”
Their vessel, the Dragonfly, a 37-foot Jeanneau Sun Odyssey cruising class sailing yacht, survived that close call and proved seaworthy as the couple negotiated its way down the Mississippi River drainage to the Gulf, and then to Florida and the Bahamas.
“We didn’t have an exact timeline in mind when we left Chicago, and once we got to Florida and the Bahamas and were wearing T-shirts in December, we weren’t very sure if we would come back,” said Scannell, who learned about the Great Loop at a trade show and found the challenge of making the trip fascinating. The planning started a few years ago. “It was definitely Greg’s idea,” said Larson, who met her future husband when he was teaching sailing at the Chicago Sailng Club. “But I was onboard from the beginning, since I’m a huge fan of taking longer trips.” She was heavily involved in her career as architect, which included work on the One Chicago Square skyscraper. “I put four years of my life into that project so it was pretty tough to walk away before it was finished,” the Ann Arbor native said, “but with the COVID pandemic dragging on, it seemed like 2020 was likely the time to take on an adventure like sailing the Loop.” She earned a master’s degree in architecture at the Chicago Institute of Technology and has worked in Germany and New York. Greg, a 2011 graduate of Ohio State University with a degree in environmental engineering, first worked in Chicago as a safety consultant but now focuses full-time on teaching sailing and taking clients on cruises in the area.
The couple eventually started their sailing charter and instructional business called On A Boat Sailing with Larson’s boat, Dragonfly. Scannell, who played hockey at St. John’s and is a licensed USCG Master Captain, said the welcoming nature of those in the sailing world was one of the best aspects of the lengthy trip, which included stops at Put-in-Bay and Toledo Beach Marina.
“Ultimately for me, it is the people you meet and the stories that you share that become most memorable,” he said. “Everywhere you go, there are people that catch your lines. It is unlike any community I have ever been in — you instantly have something to talk about, unlike any other land-based community where it takes a while to get to the friendship point.”
Larson said she developed a new appreciation for the landscape while also enjoying the solidarity with other sailors. “On a trip like this you definitely appreciate people’s openness to become your friend almost instantly,” she said. “But also seeing the vastness of the country was something special. From the waterways you can see so much and see how it all works, plus there is nature and the natural landscape involved. You really get a sense of how vast the country is.”
First Published July 17, 2021, 10:00 a.m.
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