This has nothing to do with the Bahamas (where we are now). This is a catch up post from way back in the summer when we were on Lake Michigan.  I was reminded of  my home state when my brother sent me a text message that told me the temperature was sub zero.  I was glad that we are in the Bahamas where it is always 75 degrees, but remembered what a great time we had on the less travelled side of Lake Michigan.  Wisconsin.  

When loopers get to Lake Michigan, they have a decision to make: Which side of the lake: Michigan or Wisconsin. This is my case for heading west and coming down Wisconsin. Or at least cutting over from Michigan to Wisconsin at some point to get the best of both worlds.

Below is a VERY subjective spreadsheet that summarizes the words below.

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A caveat before we get into the details. I was raised in Wisconsin. From elementary school through college I lived in Wisconsin and so when we planned the loop, we had every intention on spending at least some time here. My family lives in Western Wisconsin/Eastern Minnesota, my college (Ripon College) is close to Lake Michigan and we have friends in Milwaukee, Madison, Sheboygan, and Chicago. Wisconsin was in our future.

We went to the spring rendezvous in New Bern and heard the pitch on Lake Michigan and which side to travel: Michigan or Wisconsin. Frankly Michigan came across better during the discussion; placid harbors every 20-40 miles; beaches; fudge; tourist towns, vineyards. Wisconsin seemed like a wild land. We heard about fish boils (whatever they were) and that is the sum total of what we remember from the discussion. We looked at the waterway guide and saw that there were actually anchorages on the Northern portion of Wisconsin (in Green Bay right next to scenic Door County), then the rest of the trip was just like Michigan. 30-40 miles between harbors.

Our plan was to see as much of Northern Michigan as we could and then cut over to Wisconsin. So we went to Mackinaw/Beaver Island/Charlevoix (with day trip to Petoskey and Harbor Springs) and planned to go to South Manitou Island (anchor), then Frankfort before crossing Lake Michigan to Sturgeon bay. Our plan went awry when our roller fuller on the foresail acted up a bit and we had to cut short one moving day. So we went to Northport and when we got a good weather window, crossed from Northport to Washington Island, WI. 70 miles. We made the best decision for the time, but if we had to do it again, I think we would try our best to make it to the Manitou Islands and Frankfort and then cross.

That being said, it turned out to be a blessing in disguise. Our favorite place to date was Washington Island. We planned on anchoring for one night there, but spent three days exploring Washington Island and Rock Island–the farthest point north on Wisconsin’s Door County Peninsula. Then we moved south, taking a couple of days to enjoy Green Bay and Door County en route to Sturgeon Bay, traverse the inlet and then head south on Lake Michigan through the numerous ports to Chicago. The scenery is fantastic: There are majestic tree covered bluffs and protected harbors all around. Sailboats, trawlers, speedboats, pontoon boats and wave riders are all moving across the wide body of water enjoying the sunny day. Good part about traveling on Green Bay is that when weather is sketchy, you can still travel. For example, we had wind from the SW from 20+ knots and there were some waves in the bay, but on Lake Michigan the forecast as for 3-4 foot or larger waves. We like little waves.

Door County is worth some spending time. We talked to a bunch of people from Wisconsin and Michigan and most agreed that their favorite anchorage is Fayette in the UP of Michigan, which is one day (sailboat style) from Washington Island. There are a bunch of places to explore around Washington Island. And from the Island south to Sturgeon Bay there are numerous anchorages and/or marinas to stop to explore Door County. We stopped at Fish Creek and did the obligatory fish boil. Which turned out to be outstanding. We were skeptical about the food and had a backup plan of pizza after we left the restaurant but we all three (including our son) at everything on our plate. It was a good show and it was good food. Towns in Door county cater to tourists and you can spend weeks here; seems that half of the population of Illinois is doing just that!

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Fish boil ingredients (before boiling)

Sturgeon Bay is a good stop to go from the bay to Lake Michigan. We didn’t head down to Green Bay (the town) by boat–took our car. Didn’t seem like a very hospitable place to go by boat (especially at our speed).  The trip to the Green Bay HOF was well worth it, even for a life-long Minnesota Vikings’ fan.  Sturgeon bay has two harbor hosts (Jim and Peter) both of whom provided great information about the local area.

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Maybe you have heard of this place?

After Sturgeon Bay you are now in Lake Michigan. There are stops every 20(ish) miles. We went to Kewaunee, a town that caters to salmon fisherman. We were the only sailboat in the marina and one of two boat that weren’t fishing boats. The other was a gold looper on their way back around. Kewaunee had harley riders, a cheese shop specializing in Gouda, a really nice restaurant and a smoke shop that had smoked fish for cheap. And a custard shop. All walking distance. So good food and a sense that you may get the sh!t kicked out of you (by the Harley riders) make this a must stop for danger seekers.

Next stop is Manitowoc. 20(ish) miles from Kewaunee. Great town. Has maritime museum with WWII submarine that you can tour and hands down the best tour guide ever. Ice cream shop that has been in town for 100 years. Great marina with good service shop. Ton of good restaurants. We rented a car and went and explored Appleton, Oshkosh, FonduLac and Lake Winnebago. Fantastic harbor hosts, Dan and Fawn met us at our boat with wine and cheese! How can you not like that!

Next is Sheboygan. Home of bratwurst. Super nice marina that rivals any we have seen on the loop. Wine bar in the marina, nice docks. Town is fantastic and caters to tourists. There is even a boat with Gold Loopers who spend their summers in Wisconsin (because it is paradise) and head back down south in winter (because who really wants to be in the midwest in winter.  Crazy people.  That’s who).

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Brats, cheese, meat.  Who needs fudge and ice cream?!?!?

Milwaukee is next, though you can stop in a cute tourist town of Port Washington. We did not. We went straight down to Milwaukee and the McKinley Marina. Right in downtown Milwaukee. Walking distance to a whole host of restaurants and activities. Right by the festival grounds and there seems to be a festival a weekend. Taxi or uber to Harley Museum. With a rental car you can take a 90 minute ride (depending on how heavy your foot on the gas is), to Madison.

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And of course, beer.

Between Milwaukee and Chicago you can stop in Racine, WI and/or Kenosha, WI and/or Waukegan IL. We stopped in Waukegan and hopped in an uber for the short ride to Six Flags, Chicago//Wisconsin.

Then Chicago. Where you rejoin all the other loopers.  And carry on with the rest of the loop!


Why Wisconsin?

  • You get Georgian bay/Norther Channel type anchorages through green bay. And they are gorgeous.
  • You are unique. Most people we talk to have seen very few loopers. They love to buy you drinks and hear about your trip!
  • They have beaches!!! Seriously. We have seen two of them so far!
  • Prevailing winds are from west, so you can often travel when conditions are terrible on the Michigan side.
  • Fish boil.
  • Fish Fry

Why not Wisconsin?

  • Have to make a Lake Michigan crossing. Which wasn’t much longer than our runs up the New Jersey coast or our crossing of Lake Ontario. But you have to wait for a good day.
  • Don’t have the great Michigan DNR site to make reservations at marinas so you have to call.
  • Dunes. Really big dunes.
  • Less fudge.

We tried to get the best of both worlds by crossing to Wisconsin from Michigan once we passed by the Dunes. But we had to cut early. so basically went to Charlevoix and then West. If we had to do it again, we would make sure we got to the dunes and then head over.