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. 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. Pentwater is next, and then Saugatuck, which has an anything-goes, liberal atmosphere. Then back to Chicago, a 73-mile jog.”

Beausoleil Island, Lake Huron

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. 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 you’re not quite as remote. There are cities where you can go in and wander around if you want to.”

Mackinac Island, Lake Huron

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 [Massachusetts]. 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.”

Port Washington, Wisconsin

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,” he says. “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.”

Chicago, Illinois

Just pay attention to the weather report, Barnes 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.”