If you know anything about Wisconsin, you know it's most regarded for it's cheese, dairy, and the Green Bay Packers. I think Wisconsin is one of the staple states of the Midwest that heavily influences its personality. You can find quirky architecture, as Wisconsin was home to the famed Frank Lloyd Wright, as well as another eccentric you'll see below. Madison in particular is a hip, college town with nature and other attractions nearby. To the North, you can find what feels like an extension of Michigan's Upper Peninsula. Craft breweries and German influence can be found in Milwaukee. For a state I knew little about, I was pleasantly surprised to see a variety of things to see and do, all that fits into a short, relatively inexpensive trip.

My Favorites

1. Apostle Islands

Apostle Islands

Highlights: Sea Caves
Suggest Staying: 2-3 days
Stay Around: Bayfield, Ashland, or Washburn
Internet: Good
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I’ve been eager to visit after seeing so many breathtaking photos of this place, either in winter or summer to explore the sea caves. Unfortunately I was just getting over being sick and didn’t have the energy for kayaking, plus the weather turned and the sea got quite rough. The main town of Bayfield is nice, but if the weather is bad or you’re not planning on getting out on the water to go exploring, there’s not really much to do. There is a boat tour around the islands, some live aboard options to do some kayaking and even scuba diving to explore the sea caves, and you can also charter boats for day trips. There is some stuff to do on the mainland. The national parks website has a lot of great information and resources. There are RV and camping options available on the mainland in addition to hotels and lodges.

See & Do

  • Islands & Sea Caves. The main attraction here is the islands and surrounding sea caves which requires a boat and/or kayak. Charter a boat, take a boat tour, do a live aboard, rent a kayak from the mainland. In the summer, the lake is generally calm and easy to navigate to the caves, in the winter, you get these beautiful ice caves.

Food & Drink

  • Chequamegon Grill. Very good seafood options. Located on the lower level of the hotel.
  • Chequamegon Food Co-Op. If you need snacks, groceries, or would rather cook your own meals. Really nice grocery store with all kinds of good healthy items.


  • Getting There. The closest airport is Duluth, Minnesota, from which you could then rent a car. There may be buses as well, though I’m not sure. If you’re going island hopping you don’t really need a car. Two other options with major international airports would be Minneapolis and Milwaukee.
  • Accommodations. If opting to stay overnight on land, Bayfield is closest to the action. It will be more expensive and harder to find lodging unless you book far in advance. There are some RV and camping options here as well as hotels and lodges. Ashland is not too far and has a better selection of restaurants, not to mention being cheaper. Washburn isn’t bad, not as much selection, but you can always just go to Bayfield or Ashland.

2. Madison

Capitol Building

Highlights: Capitol, university, nature, architecture
Suggest Staying: 2-3 days
Stay Around: Marquette
Internet: Strong
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I would periodically see articles about Madison being a cool, hip, up and coming place to live, so I figured it might be a developing hipster city. At least it’s a university town which is always interesting, especially if combined with the capitol. Like Austin for example. I stayed over Labor Day weekend during the Taste of Madison and first Badgers college football game. Needless to say, it was quite packed. I was a bit underwhelmed by the city itself, but there are some really cool attractions within an hour of the city. Madison felt a bit more “upscale” Washington, DC vibe than a place like Austin or Asheville. At least as far as restaurants go.

See & Do

  • Capitol Building. I didn’t go inside, but definitely worth walking by.
  • State Street. Main area with shops and restaurants.
  • King St. Other main area with lots of shops, bars, and restaurants.
  • Marquette. Area outside of the main downtown that’s a bit less crowded with shops and restaurants.

Food & Drink

  • FEAT. Artisan dumpling and tea house. I liked this place so much I ate here twice. The dumplings are awesome and nice tea selection.


  • Wisconsin Dells. Stopped here on my way into Madison, about an hour out. Beautiful lake, took the boat tour to Witches Gulch which is spectacular. You’re on the boat most of the time, the water is calm. You’ll hop off for a 0.5 mile round trip walk through the gulch and again at a spot where you’ll see a dog jump across some elevated rocks for some past tradition. Tours leave every 45 minutes, but there’s no real schedule per se. The town has some restaurants and attractions. Reminded me of Gatlinburg and Branson.
  • Taliesin. Home to the famous architect Frank Lloyd Wright who pioneered the intertwining of design and nature. It’s a remarkable place. Guided tours are required to view the property. There are several different ones, I did the 1 hour house tour. If you happen to be out in Tucson, you can view his winter home Taliesin West. Cost: $42.
  • The House on the Rock. Definitely one of my top favorite oddball attractions. It’s not even really that oddball. Only 10 minutes up the road from Taliesin, Alex Jordan designed and helped construct this place over about 20 years. It’s part home, literally built into the rock, and two additional areas with a 200+ foot whale fighting a squid, the world’s largest carousel, largest chandelier, automated music machines that play when you put in a token, and concludes with a Japanese zen garden. It’s truly incredible, a must see in my opinion. There are bathrooms throughout, places to sit for breaks, and food for purchase along the way. The house itself is very cool, I assume inspired by Frank Lloyd Wright. Plan 3-4 hours to explore everything. Cost: $29 (online discount).
  • Epic. A healthcare IT company with an amazing campus that looks like Stanford and Google campuses had a baby. Fantasy themed, beautiful buildings, and you can even take a self guided tour during certain times/days. A fun little stop. I wish more companies had a better balance of professional and fun built into their culture.


  • Accommodations. I ended up staying in a hotel suite on the other side of the lake since I don’t like staying in a crowded downtown if I have my car. Plus this option was cheaper. Downtown might be preferable, but I also really liked the Marquette area which was hip and more chill than downtown, so it really depends on what you’re looking for. All options are short drives to whatever you plan on doing.
  • Taliesin & House on the Rock. I did these in the same day. Taliesin tours are timed, House on the Rock is not. I didn’t want to rush in the morning, so I scheduled a later 3:30p tour time for Taliesin and did House on the Rock late morning. I also stopped by Epic on the way. That itinerary worked perfectly to maximize the day.

3. Milwaukee

Historic Third Ward

Highlights: Museums, breweries, art, lake
Suggest Staying: 1-2 days
Stay Around: Shorewood or Downtown
Internet: Strong
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This major Wisconsin city has some nice things to do and people seem very friendly, but I generally found the city not overly exciting and kind of run down in many areas. That said, if you like beer and German food, this is the place for you! Milwaukee is known for it’s breweries, cheese, and German influence, so you’ll find many beer hauses and sausages. Locals absolutely love their city, which I can appreciate if you’re into what it offers.

See & Do

  • Historic Third Ward. Hip artsy area with a mix of apartments, shops, and restaurants along the river.
  • MLK Dr. Has some restaurants and a historic spice house.
  • The Domes. Botanical garden. Takes about 30-45 minutes. Domes themselves are pretty cool, at least for a photo.
  • Public Museum. Natural history.
  • Milwaukee Art Museum. I didn’t go inside, but the outside looks amazing.

Food & Drink

  • Milwaukee Public Market. Very cool market with tons of food stalls serving made to order food.
  • Milwaukee Brat House. Sausages and other German food.
  • Fava Tea Company. Cool tea shop with a huge variety of traditional and blended loose leaf teas. All sorts of flavors and great staff. Several locations in the area. One of my new favorite tea shops.


  • Wauwatosa. Cute little modern village.
  • Sheboygan. Beaches and surfing on Lake Michigan.

Other Considerations

Copper Falls State Park

Copper Falls

Great little stop for lunch and light hiking through this beautiful river canyon if you’re traveling between the Porcupine Mountains and Apostle Islands. The Doughboy’s Loop will take you past Copper and Brownstone Falls. I think it was about a mile or two. There is also a lake in the park, picnic areas, and a park store. You can’t really get down into the canyon for most of the route, but it’s a really nice forest hike primarily along the canyon rim. There is some elevation involved, but it’s pretty moderate. I wouldn’t consider it a must see, but it was a nice driving break to stretch your legs for sure. I can imagine if you live in the area, it would be a nice place to spend the afternoon.

Great River Road Scenic Byway

National Eagle Center

This national scenic byway was built decades ago along the Mississippi River to transport goods when the river levels were too low for boats. It’s pretty impressive in that it stretches all the way from Minnesota to Louisiana. I drove along this route from Minneapolis to Madison, which was only about 45 minutes longer and passed through a few small towns. I was expecting to be able to see more of the river along the way. I would say this drive is more of a nice break from the monotony of the highway versus something supremely beautiful. However, there are some parks along the way, though I did not have time to explore them. I did visit the National Eagle Center which rescues eagles and has some interesting information about them. Interestingly in the fall (Sep) and winter (Dec/Jan), this area is packed with Golden and Bald Eagles respectively for nesting. I didn’t even know there were eagles in this part of the country, but apparently they exist wherever there is good fishing. I would recommend starting your journey at the visitor’s center in Hastings for maps and information.

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