Let’s assume you’ve chosen to stay downtown in the Third Ward or The Upper East Side — anywhere that’ll give you closer access to Lake Michigan. Let’s also assume that it’s a beautiful summer weekend because you would be insane to visit Milwaukee in February.
Wake up early. Being right on Lake Michigan means getting up to watch the sunrise, at least once. No whining — you’ll thank me later. May I suggest you find your way to McKinley Beach with a blanket?
Once the sun is up, walk just a bit south down Lincoln Memorial Drive and stop for a cup of coffee at Colectivo, but be careful not to fill up on bakery items as you’ve got to save room for brunch later.
Once you’re done with breakfast go back and take a nap. The city’s not awake yet. You were crazy to get up this early.
Around 10:30, head over to Café Benelux in the Third Ward. You’ll likely have to wait for a table, but it’ll be worth it. Order the beignets to start (don’t share) and the quinoa skillet.
You’ll be stuffed, so best to walk off this mess. Head over toward the lake again, particularly toward Henry Maier Festival Park. If it’s summer in Milwaukee, there’s probably some kind of festival going on. If not, head up to the Milwaukee Art Museum — it’s the weird white winged building just north of the festival grounds. Fin fact: one of the Transformers movies was filmed there.
Once you’re done pretending like you know anything about art, head west on Mason St. toward the river and find the Bronze Fonz. Pose for a picture with your thumbs like you’re saying, “Who thinks the Packers are the sexiest football team in America? This guy!”
Walk south down the river and back into the Third Ward. It’s time for a beer. Stop by the Milwaukee Ale House and have a cold Sheepshead.
Go the Milwaukee Public Market and head to C. Adam’s Bakery and get a slice of toasted white chocolate coconut cream pie or a cup of chocolate mousse. Find the Thief Wine Shop and get a bottle to enjoy later along with a packet of fresh cheese curds from West Allis Cheese & Sausage Shoppe.
If you’re still hungry for dinner, find your way north to Brady Street and grab a table at Cempazuchi for Milwaukee’s best authentic original Mexican food. Sip the margarita special of the day and get the fish tacos.
Go back to your hotel and get yourself prettied up for Milwaukee’s famous Edelweiss river cruise. At only $18 per person and on Friday and Saturday evenings, what else would you want to do with that awkward pre-bar twilight time? Get drunk on the river.
If you were able to keep your tequila down and didn’t get too motion sick, stumble your way to your nearest bar (probably Ale Asylum or the Pub Club). Milwaukee is all about enjoying yourself to the last drop, so pull up a stool with your buddies and order a Miller Lite.
Cars: Uber and Lyft work beautifully in Milwaukee and typically cost less than cabs.
Public Transportation: Milwaukee County Transit System (bus system) is useful but time-consuming; however, it will take you all over the city and then some.
Bikes: Check out rentable bikes all over the city.
Foot: It’s an easy walking city if you’re really in the mood, but I would suggest staying within the Upper East Side if you’re on foot.