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A Cool Girls Guide to Milwaukee and More

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Where I was born and raised. Its underrated. Especially easy to tack on as a day or weekend trip from Chicago! Plus a few other surrounding spots as well
Map
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Hotels

 
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Also contains Wolf on Broadway- a really good lunch spot
Kimpton Journeyman Hotel in Downtown Milwaukee | Kimpton Hotels
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Artsy Hotel in a great location. Walkabout to nearly everything
Saint Kate - The Arts Hotel, Milwaukee, USA
 
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Beautiful and Modern. Kind of a business sort of hotel
Hyatt Place Milwaukee Downtown, Milwaukee, USA
 
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Pop in during Christmas to check out the decorations
The Pfister Hotel, Milwaukee, USA
 
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Madison: Stylish and great location. I tend to stay Hotel Indigos when given the option
Hotel Indigo Madison Downtown, an IHG Hotel
 
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Super stylish boutique hotel in Madison
Graduate Madison, Madison, USA
 
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Near the Harley Davidson Museum. Hence…Iron Horse. Get it?
The Iron Horse Hotel, Milwaukee, USA

Where to Eat/Drink

 
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My favorite brunch spot. Prepare for a wait
Uncle Wolfie's Breakfast Tavern & Nite Wolf Ramen
 
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Great for lunch and cocktails. And inside The Journeyman :)
The Wolf on Broadway
 
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Delicious. Get the lobster roll, some sweets and Milwaukee souveniers
Milwaukee Public Market - Fresh Food. Local Vendors.
 
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They do lil Ski Chalets in the Winter. Wauwatosa is worth checking out as well
Buckatabon Tavern & Supper Club
 
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The Desserts are SO good. I loved the pandan creme brulee
Odd Duck
 
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Coffee Flights- do they get cold though?!?! If you go to Wolfies but have to wait, this is walking distance
Pilcrow Coffee
 
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Hidden Spy themed restaurant. Been there agessss
SafeHouse
 
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Funky coffee, originally from Chicago
Goddess and the Baker, Corners of Brookfield, WI
 
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Great Mexican spot that I go to everytime Im in town
Botanas Restaurant: Home
 
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My favorite coffee spot in MKE, maybe not as “cute” as colectivo but imo the coffee is better
Stone Creek Coffee - Bringing specialty coffee from Farm to Cup.
 
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Another great coffee spot, with a really nice location by the lake
Colectivo Coffee on the Lakefront
 
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Delicious and recomended often for a reason
DanDan
 
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Just put Jo-cats as an example- anywhere on Brady Street is fun!
Jo-Cats Pub
 
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great date spot in the beautiful and vibey Tosa Village
The Bartolotta Restaurants | Fine Dining Restaurants in ...
 
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Old school style custard. a must
Leon's Frozen Custard
 
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Soosh in the popular Bay View neighborhood
Hungry Sumo
 
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icecream-y cocktails with a cute patio- they deck it out for Christmas too
At Random
 
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a fancier dinner, right on the…. you guessed it, harbor
Harbor House
 
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Up North Outdoors vibe bar. I believe there are 2 locations
Camp Bar | Tosa
 
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another date night spot, one of the fancier restaurants
Sanford
 
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another food option and frequently featured in “best of” lists
The Diplomat
 
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great burgers in Historic Third Ward- you're spoilt for restuarant locations here
Bavette La Boucherie
 
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great cocktail place in a great neighborhood
Goodkind
 
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as seen on Top Chef though Ive not actually tried it yet
Lupi & Iris
 
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Wauwatosa in general is very worth checking out
Le Rêve Patisserie & Café
 
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Breakfast diner, also in Wauwatosa but a bit off the “main drag”
Blue's Egg
 
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eat and drink out of an old airstream
Vagabond
 
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get the cheese curds and obviously a drink
Lakefront Brewery | Born in Riverwest Raised all over
 
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Speakeasy
Shanghai MKE at Black Cat Alley | Speakeasy & Absinthe Bar
 
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Another speakeasy, they do sell cigars here too. But barely
Shaker's Cigar Bar
 
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Kohler does everything well and this is no different
Kohler Wisconsin Spa
 
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If you to Madison: Cheese!
Fromagination - Wisconsin Artisan Cheese
 
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Madison: I used to go here when it was nothing more than a farmers market stall. Its so delicious
Spicy Cheese Bread
 
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Cedarburg: Incredible candy store. So yum
Amy's Gourmet Chocolate Candy Caramel Apples
 
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Cedarburg: cute lil Winery. Cedarburg is worth an afternoon explore
Cedar Creek Winery - Cedar Creek Winery
 
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You wouldnt expect such a good little restaurant to be here but it is indeed, very very good
The Norbert
 
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Tiki Bar for some kitschy fun
Foundation
 
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Old School Italian Bakery. Milwaukee has a deep, rich history of Immigration- Italian, German, Hmong, Mexican etc etc. Theres some great places to eat and I recommend you seek them out!
Peter Sciortino Bakery
 
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Cute new-ish coffee spot in Wauwatosa village
Vendetta Coffee
 
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Retro Electronic Repair themed Speakeasy
Don's TV & Repair Speakeasy
 
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For my Empanada craving
La Masa Empanada Bar - Brady St. Milwaukee WI
 
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Bougie Restaurant in Madison. Someone let me know if its good- Ill be honest, I added it because I saw it on Top Chef but Ive never been to this one
Fairchild

Things to Do

 
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A moving bar in the city. MKE loves beer
Milwaukee Private or Public Pedal Tavern Tour
 
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2 Week Festival over summer, super affordable
Summerfest
 
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If youre just here for a day I recommed a tour!
Milwaukee Tour✌️
 
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the “wings” of this museum actually open and close
Milwaukee Art Museum
 
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MKE Brewery Tours. Not sure if its still like this but if you, you pay for a 2 hour time slot and its all you can drink within that 2 hours
City Brew Tours Milwaukee | Milwaukee, WI
 
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Theres a lot of dark s**- think Dahmer. If spooky is your vibe check it out
Shakers Original Historical Ghost Tour
 
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Absolutely stunning day trip from Milwaukee
Devil's Lake State Park in Baraboo, Wisconsin.
 
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Harley Davidson museum if thats ya vibe
Skip The Line: Harley-Davidson Museum Admission Ticket with Audio Guided Option
 
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The dates change each year depending on climate but assume Mid to late January and February
Winter Realms by Ice Castles
 
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get out on Lake Michigan. Obviously sunnier only
Adventure sailing in Milwaukee by Sea Dog Sailing | Milwaukee, WI 53202
 
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obviously at its best in the autumn
Apple Holler
 
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fresh produce and delicious apple pie baked in a paper bag
The Elegant Farmer
 
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the miller factory in general is worth checking out
Historic Miller Caves
 
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great at Christmas time (or anytime)
The Pabst Mansion | Milwaukee, WI | Museum, History & More
 
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for obvious reasons this is most popular during and after games. When I was growing up the Bucks were NOT good. They are now so its really come alive
Welcome to Deer District
 
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An italian style villa you can visit in Milwaukee
Villa Terrace Decorative Arts Museum
 
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Beer garden next to a community pool, only open in summer for obvious reasons
The Landing at Hoyt Park
 
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Great shopping and lots of cafes
Historic Third Ward | Milwaukee's home for art, dining ...
 
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little bowling alley and a bar
Koz's Mini Bowl
 
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has everything you could think of
Antiques On Second, Antiques, Milwaukee WI
 
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Drag Brunch 🩷
Hamburger Mary's Milwaukee
 
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Madison: one of the last free remaining zoos in the USA
Welcome to Henry Vilas Zoo | Madison, Wisconsin
 
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Cedarburg: Biking and walking trail. Cedarburg is so cute during Christmas time!
Interurban Trail | City of Cedarburg
 
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A weird and wonderful tourist site. Its honestly difficult to explain you just have to see it yourself
House on the Rock
 
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Arcade Bar in milwaukee if you want to feel like a kid again
Up Down Arcade Bar

Etc Etc

 
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E-sim for USA and Canada
4G eSIM card high-speed Internet access in the United States and Canada (buy now and get QR code) - Klook
 
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“the Hop” aka Milwaukee's (small) train system. Its pretty new so the line isnt comprehensive but its also currently free!
Milwaukee The Hop
 
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Easy 2 Hour train Between Chicago and Milwaukee
Welcome to Amtrak Hiawatha | Milwaukee - Chicago