Only a handful of crewed charter yachts spend summers on the Great Lakes. Their captains call the region one of the most beautiful—and least traveled—cruising grounds in the world.

Capt. Mike Witters has had the same conversation countless times during the past 10 years. That’s how many summers he’s spent as captain aboard the 90-foot Stephens Trilogy out of Petoskey, Michigan, a city of fewer than 10,000 souls in the northern part of the state, where the tip of a middle finger would be inside of a mitten.

“I can’t tell you how many charter guests have told me it’s crazy that the Great Lakes are so unknown,” he says. “They say they’ve been to New England or Maine a thousand times, and this is new and just as beautiful. They can’t believe there aren’t more charter boats running around. It’s a great, unknown wonderland.”

Capt. Graham Barnes of the 84-foot Palmer Johnson Captivator says the same thing: “If all of your cruising is in the Florida Keys and the Bahamas, then you need to come up for a summer to Lake Michigan. It’s a beautiful spot. People don’t know what they’re missing.”

That’s an awful lot of ignorance about the largest group of freshwater lakes on Earth. The Great Lakes comprise more than 80,000 square miles. As a matter of context, the whole of the Bahamas is not even 7 percent of that size. You could lay the entire state of Nebraska atop the Great Lakes, and water would still be visible around the edges.

While hundreds upon hundreds of crewed charter yachts are available each summer in the Bahamas, New England, and the Mediterranean, fewer than a half-dozen are typically advertised in the freshwater paradise that is the Great Lakes. That’s because of all the effort it takes to get there, with a yacht either snaking its way up the rivers of America’s Heartland or taking the long way around Nova Scotia and west across the St. Lawrence Seaway. After all of that effort, the owner has a charter season that’s only three, or maybe three-and-a-half months long if he gets lucky with the weather. And the yacht is in a place where so few other crewed yachts are based that people—guests and brokers alike—rarely think of it as an actual charter option.

“I think the thing is that Chicago has a really cold winter,” Barnes says. “You’ve got people up there who can afford a boat, and they say, ‘Hey, let’s go to the Bahamas.’ And the people in other parts of the country don’t know that Lake Michigan does have a summer. It was gorgeous this year, with 92- and 93-degree weather for 10 days on end. I just don’t think it’s advertised and marketed enough.”

Because of its size, the Great Lakes region offers multiple charter itineraries. There is no “milk run,” so to speak, with yachts cruising along the same ports or islands the way they do on the French Riviera or in the Virgin Islands.

Barnes says the ideal itinerary depends on where you want to start. Options include downtown Chicago, Milwaukee, Door County in Wisconsin, and beyond.

“A 10-day charter for me would be picking up in Chicago, cruising up to Racine, then Milwaukee, then Sheboygan or Port Washington, then the Door Peninsula and Sister Bay, then cross Lake Michigan and see Mackinac Island, which is right by the Lake Huron Straits,” he says. “Then go down Lake Michigan and stop in places like Harbor Springs. You’ll be walking around the town, and there will be bronze drinking fountains where the water is fresh, fresh, fresh. If you were sitting in the marina there, you’d think you were in the Exumas. You can see 30 feet down, the water is so clean and clear. Then go to Leland, where the coastline—well, you could be cruising in Cornwall, England. They have these sand dunes that are so big and grand that you’d think you were cruising past mountain terrain. Pentwater is next, and then Saugatuck, which has an anything-goes, liberal atmosphere. Then back to Chicago, a 73-mile jog.”

Witters says there are three general regions where he likes to bring charter guests. First is the North Channel on Lake Huron.

“It’s like Maine,” he says. “It’s clear, fresh water, trees and bears, and mountains. It’s gorgeous. You can easily do a seven-day charter there out in the middle of nowhere. There are little islands all over the place, and you’re saying goodbye to the world. That’s the getting-away-from-everything charter.”

There’s also the Thousand Islands, Witters says, which offers a different experience on the St. Lawrence Seaway and Lake Ontario. “It’s the same idea as the North Channel, but there are houses everywhere,” he says. “The Singer Castle is there, and it’s really neat. You’re still anchoring out every night, but there’s some sightseeing. You’re not quite as remote. There are cities where you can go in and wander around if you want to.”

Last but not least on Witters’ list is an exploration of Lake Michigan, starting in Traverse City. “You go off to Manitou, then Lake Charlevoix, then Bay Harbor where there’s golf and the city of Petoskey where there’s a casino. Then you go to Harbor Springs, which is a quaint little place that’s as pretty as Cuttyhunk. Then I might go to Beaver Island, where there’s nothing but quiet to enjoy, and then Mackinac Island, with all the horses and bicycles. Chicago is miles away. It’s a whole other world.”

Both captains say that late June or early July is the earliest you want to arrive, to give the water and air a chance to heat up after the frigid Midwest winter. Often, the weather remains good through the middle of October—and the waters remain clear for scuba diving, which Barnes says is fantastic. “You can see a shipwreck lying in 20 or 40 or 90 feet of fresh water, preserved like you wouldn’t believe. If you don’t mind putting on a nice, thick wetsuit, you’ll be fine. Instead of seeing a bunch of eels and fan-palm coral, you see a boat that looks like it just came off the showroom floor. It’s quite a sight.”

Just pay attention to the weather report, he advises. Conditions can change quickly on the Great Lakes, and whether you’re diving, golfing, or sightseeing, you need to have an adaptable frame of mind.

“With Lake Michigan in particular, you can feel like you’re in the middle of the Exumas or in the middle of the Bering Sea,” he says. “She has quite a personality, that lake. She will show you three or four sides of her face inside of a minute. She can be a funny little thing, but what a gorgeous thing she is.”

Trilogy is part of the Churchill Yacht Partners charter fleet. Captivator is part of the Neptune Group Yachting charter fleet. Any reputable charter broker can tell you more or help you book a week onboard in the Great Lakes.