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It's 2:30 p.m. when our Apostle Islands adventure starts in earnest. We leave the breakwater at Port Superior Marina aboard Twilight, raise the sails, and begin a 10-mile beat north along the Wisconsin shore to Oak Island, where we'll tuck in behind the sand spit off its southern tip and be out of the northeast wind. Our first tack takes us close in toward Madeline Island's western shore and directly across the path of the ferry that bounces back and forth between the small town of La Pointe and downtown Bayfield, on the mainland.

That hazard to navigation astern, we tack, and I deem it time to sample a Miller High Life, the beverage of choice for the next five days at the insistence of Milwaukee native-turned-New Englander Mike Lee. Or rather, that's the beverage for the boys. The girls on board—my wife, Sue; our sailing pal, Paula Devereaux; and Mike's soon-to-be wife and the ship's photographer, Marianne Groszko—want nothing to do with a can of what made Milwaukee famous and instead choose to toast our departure with "Leinies," freshly bottled by the Leinenkugel Brewing Co., the "Pride of Chippewa Falls." With the morning's rain now well to the east, the mid-July sun burning through, and a fresh breeze on our nose, it's a heck of a way to kick off our search for beer, brats, and bears in the heart of the Midwest.

I wish I could say that I'd always dreamed of sailing on the largest lake in the world (as measured by surface area, I'm reminded) and that the 22 islands that lay ahead of us—21 of which make up The Apostle Islands National Lakeshore—had long held a spell over me with their rugged tree lines, nests of bald eagles, deserted beaches, sandstone cliffs, and spectacular sea caves. But that wouldn't be entirely true. Sure I'd heard of Wisconsin; what cheese lover hasn't? And, well, everyone knows there are Great Lakes up north somewhere. But as to knowing what's in 'em and around 'em, well, that's another story. And that story began about this time last year, when Cindy and Dick Kalow, owners of Superior Charters, offered to let someone at Cruising World use a 2008 Jeanneau 36i to explore what they described as the most lovely and interesting cruising grounds you could find between the three coasts.

"We're going where?" Sue asked when I told her about our destination. "Apostle what? Never heard of it," Paula replied when we asked her along. "Duluth, Minnesota. Where's that?" I said to myself when I looked into airfare from Boston and discovered that Duluth International was the closest airport, being just one state removed and a couple of hours' drive from the marina.

As Midwest natives, Mike and Marianne, of course, knew all about Bayfield and its bustling waterfront, artists, shops, restaurants, and Friday-night fish frys. They'd visited Madeline Island, the only one of the Apostles not in the park and the only one with a town and residents. They discounted the rumors that the lake water would be too cold for swimming and that we'd need to pack winter clothes to survive the summer nights. And locals' pride in the quality of their thunderstorms aside, they assured us that despite what we'd read, chances are we wouldn't be sunk by the wind, hail, lightning, waves, and tornadoes described in the cruising guides.

The five of us met Sunday night at the boat, then drove the next morning to a full-sized grocery store in Washburn, 20 minutes to the south, and stocked up. Should you make the trip, I'd highly recommend putting in at the Time Out diner for their Contender Omelet: four eggs stuffed with hash browns, onions, peppers, and cheese. That'll stick to your ribs for a while.

Back at the boat, we decided Oak Island would make for an easy first-afternoon sail, a secure anchorage for the night, and a good jumping-off point the next morning. As we'd come to find out, anchoring in the Apostles—there are no moorings—is simple. Mind which way the wind's blowing and duck into the lee of a nearby island. The trick is to always have a backup, just in case the wind shifts unexpectedly.

Beating our way up West Channel, we discover that sailing in these narrow waterways between islands is going to take some getting used to. As we close Basswood Island on port tack, we're headed by the wind bending along the shore. Then, a mile or so later on starboard tack, we're near the mainland and find we're headed by the wind filling down the lake. Our boat speed is impressive, but our progress is slow, and as the afternoon fades, the wind goes with it. Off in the distance, we can see a wall of fog lurking on the open lake, and since no one's keen on getting lost in the mist, we motor the remaining few miles to our anchorage and drop the hook in about 12 feet of water. Ashore, we splash into the lake, delighted by its lack of salt. And then as we dry off and explore the point of land, we watch fingers of fog crawl over the mainland hills and creep downward into Raspberry Bay. Back aboard, we grill chicken and cook up a pot of locally grown black wild rice. Night approaches, and the islands to our west and east fade into a cloud of mist as darkness descends.

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