The Places You Find When You Leave the Main Route

We began on September 8, after waiting out an early gale on Lake Michigan. Chicago was our first major stop, and it was also our first reminder that the Loop was going to make familiar places feel strange.

We stayed at DuSable Harbor, just off downtown. It was more expensive than the marinas we had used up to that point—about $3 per foot—but it put us within walking distance of Navy Pier, restaurants, grocery stores, the lakefront path, and the whole bright city-at-night experience.

We did the usual Chicago things. Deep-dish pizza. Italian food. Walking and biking until we had worn ourselves out.

But the best part was leaving.

To continue south, we went through the Chicago lock and passed through the skyline by boat. The buildings rose directly from the river's edge. The city looked less like a place to visit than a narrow passage through which we had somehow been allowed to steer our home. Chicago was the first lock of the trip. It also felt like the first real crossing into a different way of traveling.

A lot of the Great Loop is practical. You learn to value places for what they make possible.

Chattanooga was one of those places. We went up the Tennessee River toward Knoxville and then came back through Chattanooga several months later. The river curls through cliffs and broad bends before you reach town, and we arrived in the fall, when everything looked better than it had any business looking.

The marina itself was basic: power, water when it was not freezing, no showers, no laundry. But it was inexpensive and close to downtown. That was enough. We could walk to restaurants, find green space for the dog, and visit the aquarium. When grocery options were limited, we tested a new system: grocery delivery to the Buffalo Wild Wings parking lot.

It worked perfectly.

That is not the kind of detail that ends up in a tourism brochure. But it is how you remember a place after living aboard for nearly a year. Not just by the views, but by whether you can get dinner, walk the dog, do laundry, top off supplies, and wake up somewhere worth seeing.

Dog Island, on Florida's Panhandle, was memorable partly because it had so little going on.

It is a boat-in community with a small marina built for small boats. The process of staying there felt almost unofficial: find the local contact, put $20 in an envelope, and use a slip as long as the owner does not need it. There were no marina amenities, no restaurants, no power or water at the dock.

There were, however, people.

We met the mayor. We met residents. We were invited to shower at someone's house and had drinks with locals. In the right season, when nesting birds were not a concern, our dog could run off leash on the beach. People gave us fish they had caught. We collected shells and carried many of them with us for the rest of the trip.

Dog Island was not a resort version of remote Florida. It was the real thing: a place that required a boat, a little planning, and a willingness to do without the usual conveniences. It also served a practical purpose for Loopers making the Big Bend crossing, cutting distance from the larger, better-known launching points. But we remembered it for the quiet, the shells, the beach, and the people.

Crystal River was the opposite kind of surprise.

We expected a manatee town to feel overdone—tour operators, crowds, souvenir shops, the whole thing. Instead, it felt manageable and local. The marinas were expensive, so we anchored in protected water for most of our stay. From there, the dinghy became our daily vehicle.

That is one of the pleasures of traveling this way. You anchor the larger boat and then spend the day moving through an entirely different landscape in a small one. Restaurants, groceries, springs, and little side channels all become accessible. You start measuring distance in dinghy rides instead of car trips.

The manatees were the reason we came, and they did not disappoint. With the right awareness of the rules and the conditions, we could reach the springs without paying for a tour boat. The experience felt less staged than we had expected: cold clear water, quiet coves, and animals moving through the springs with the casual certainty of creatures that had been there long before the boats arrived.

People talk about the Everglades as if the entire place is trying to kill you. We did not find it that way.

We went twice, spending perhaps 11 or 12 nights there in all: once on the way south and again after wintering in the Keys. It became our favorite anchoring area until we reached Georgian Bay. There were protected places to sit through bad weather, islands of sand and shell, long dinghy explorations, and excellent fishing.

We caught redfish, speckled trout, flounder, and other fish familiar from Gulf Coast waters. One night, outside the national-park boundary in the Ten Thousand Islands, we had a bonfire with friends. Another week was spent buddy-boating with friends in their Ranger Tug.

It was the first part of the Loop where we felt truly remote. Not isolated exactly. Just removed from the ordinary machinery of life. No roads nearby. No city lights. Nothing much except water, weather, birds, fish, and the need to study your charts before you made a bad decision.

There are crocodiles in South Florida. There are alligators. There is weather. But the Everglades did not feel threatening to us. It felt big, forgiving in some ways, and far more beautiful when a storm was moving in.

The Dry Tortugas was the clear winner for us.

The national park lies about 70 miles west of Key West. Most visitors arrive by ferry or seaplane, stay for a few hours, and leave. We waited for a weather window, traveled with a small group of other Loopers, and stayed three nights.

It cost us less in fuel than it would have cost two people to make the short ferry visit. That was one of the recurring oddities of the Loop: once you own and operate a boat, the inaccessible places can become comparatively affordable.

The water around Fort Jefferson looked unreal. Fish were everywhere. We saw giant grouper, lemon sharks, frigatebirds, and more life than we could have named without looking it up. Fishing was allowed in the designated historic area around the fort, and it was good enough that we joked about staying until we ran out of fresh water.

We had considered going to the Bahamas, as many Loopers do. But winter weather can limit movement there, and we decided not to go. The Dry Tortugas became our alternative. It did not feel like a consolation prize.

Later in the trip, after going up the East Coast and passing the Statue of Liberty, we reached Troy, New York. There, Loopers have a choice. Turn west into the Erie Canal, or go north through the Champlain Canal toward Lake Champlain and Quebec.

We went north.

Lake Champlain was one of the best summer cruising environments we saw: mountains around the water, fishing, good marinas, state parks, and enough anchorages to keep someone busy for weeks. It was also where the trip began to shift again. The farther north we traveled, the more the Loop seemed less like an American boating route and more like a continental one.

Crossing into Quebec made that change immediate.

Chambly was perhaps the greatest surprise of the trip. It was only a short distance from the U.S. border, but the atmosphere changed all at once. French was everywhere. So were French menus, French conversations, bike paths, parks, and a different sense of public space.

The Chambly Canal is only about nine miles long, but it is memorable because the water runs nearly level with the land. People walk, ride bicycles, and stop to watch boats pass through. The canal feels less like a piece of marine infrastructure than a long public park that happens to have locks in it.

We bought a Parks Canada mooring pass and used it constantly. It allowed us to stay at lock walls throughout Canada, and it quickly became one of the best values of the entire trip. The lock staffs were helpful, the settings were often park-like, and each stop made the route feel less transactional and more communal.

Montreal was bigger than we expected. We spent nine nights there between Old Montreal and the Lachine Canal, and there was no shortage of things to do: restaurants, shopping, Cirque du Soleil, biking, ziplining, and simply walking around a city that felt lively without feeling hostile.

The Montreal Yacht Club had a current at its entrance, which worried some boaters. We watched boats of all sizes come through without much trouble. Once inside, we were in Old Montreal for about $2 per foot.

Then came the Lachine Canal.

The canal has an eight-foot air-draft limit. To use it, we removed the radar, lowered the mast, and made the boat short enough to pass under the bridges. It was a lot of work for a route that most Loopers cannot use. But it gave us five nights in a different part of Montreal, traveling through locks and along waterfront trails, markets, and neighborhoods that we never would have seen otherwise.

The radar came off. The boat cleared the bridges by about four inches. And for a few days, we moved through the city at canal speed.

Ontario brought the Trent-Severn Waterway, 45 locks, and Bobcaygeon, a busy little town with boats of every possible description—jet skis, pontoons, cruisers, fishing boats, and Loopers tied to the wall.

We learned that locals pronounce it "Bob-cajun," a correction delivered with enough good humor that we did not mind getting it wrong first. We also discovered the Tragically Hip song about the town and listened to the band for much of the rest of the trip.

Then came Georgian Bay, the North Channel, and Killarney.

Killarney is a useful stop: a place to resupply, eat well, walk trails, and prepare for what lies nearby. But its real value is geographic. It sits near Killarney Provincial Park and provides access to the Bay of Islands and the North Channel. The landscape there was unlike anything we had seen on the rest of the Loop: dark pines, bright rock, clear water, and a dry, rugged feeling that reminded us more of the American West than of Ontario.

We picked blueberries on trails. We ate at the lodge. We sat in anchorages where the water was so clear that it made most other water look unfinished.

After that, the trip began to close in on itself. We returned through Michigan, passed familiar coastal towns, and finished 340 days after we had started.

What stayed with us was not a ranked list of destinations, though we had one. It was the sense that the best parts of the Loop usually appeared after making the less obvious choice: the canal north instead of west, the smaller marina instead of the obvious stop, the anchorage instead of the slip, the island that required a dinghy ride, the city reached by water rather than highway.

The trip was a loop on the map. It never felt circular while we were living it.