Friday
9 a.m. | Start Strong at Canela Cafe
Canela Cafe, with its wide-ranging menu featuring everything from chilaquiles and chicken and waffles to supreme pancakes and hearty omelets, is where you’ll find Tommy as we embark on this grand adventure. It’s his go-to weekend breakfast spot, and within minutes of settling into a booth, you'll understand why.
11 a.m. | Get Lost in Downtown Books
After a leisurely breakfast, make your way downtown to Downtown Books, Tommy's favorite literary sanctuary. The racks are piled floor to ceiling in never-ending rows, overflowing with nearly every genre, author and topic you could possibly think of in a space that’s so much larger than you ever imagined. It’s the kind of place you can wander through and stumble across a book that calls your name every time.
Noon | Brunch at Allie Boy's Bagelry & Luncheonette
Allie Boy's Bagelry & Luncheonette is a hidden gem and a charming spot for lunch. Order Tommy’s favorite: the Latke Waffle or one of their well-loved menu breakfast sandwiches, shmears and more. The vintage lunch counter mixed into a contemporary cafe manages to feel both nostalgic and fresh. On weekends, there is a bit of a wait, but we swear on Tommy’s influencer career, it’s worth it.
2 p.m. | Upgrade Your Look at All Goods
As morning gives way to the afternoon, head to the recently opened All Goods for a dose of retail therapy. This curated shop captures Milwaukee's vibe in an extensive collection of unique, vintage pieces that’ll upgrade your style. No matter what you’re looking for – vintage sportswear, stylish sweaters, a new hat or the perfect accessory to complete your look – you'll have a new wardrobe fit for the mayor (Tommy) himself.
6 p.m. | Catch a Film at The Oriental Theatre
The Oriental Theatre is the next stop on this magical mystery tour. This 1927 palace borrows from Indian, Moorish, Islamic, and Byzantine architectural styles and is one of the most ornate settings to catch a film. The theatre’s iconic marquee lights up with the latest blockbusters alongside indie films and special screenings that you just won’t find in other metroplexes. Grab a ticket and settle into a one-of-a-kind experience in this historic cinema.
8 p.m. | Dinner and Custard at Kopp's
For dinner, there's no other destination that captures Milwaukee's soul quite like Kopp's Frozen Custard. It’s Tommy’s favorite custard in Milwaukee, and all it takes is one spoonful of the rich, creamy creation to realize why. The jumbo burgers will fill your stomach, and Kopp’s popular flavor of the day will fill your heart with a little extra Milwaukee love.
Saturday
9 a.m. | Load up at Uncle Wolfie's
Day one was fun, so why slow things down? Start Saturday morning bright and early at Uncle Wolfie's Breakfast Tavern. The atmosphere and buzz of a brunch crowd on the weekend create a special atmosphere surrounded by great people. The menu features breakfast staples with a little culinary creativity, making Uncle Wolfie’s one of your (and Tommy’s) favorite brunch spots in the city. You just haven’t been there yet.
11 a.m. | For Serious Style: Niche Exhibit
Fashion is a huge part of Tommy’s life. So, it’s no surprise that our next stop is Niche Exhibit. This reservation-only shop deals in rare and curated pieces that you won't stumble upon anywhere else. Check out everything from old tour merch to high-end and hard-to-find brands. Milwaukee's style runs deep; you just have to know where to look.
1 p.m. | Stock Up at Nehring's Sendik's
Swing by Nehring's Sendik's on Downer, a cozy family-owned grocery store that Tommy stops in often, drawn by their top-tier paninis. Grab a bite for lunch, a nice piece of bakery and an emergency snack for later.
2 p.m. | Wander on Your Own Terms
Spend your afternoon exploring Milwaukee at your own rhythm. Tommy’s the kind of mayor that’s not going to tell you what to do. He wants you to find your flow in a way that’s as unique as he is. Whether that means wandering through Bay View's vintage shops, checking out galleries in the Third Ward or claiming a patio somewhere with good people and cold drinks, that’s completely up to you. The day is yours. Seize it.
5 p.m. | Ascend to The Outsider
As afternoon turns to evening, head up to The Outsider, Tommy's favorite rooftop bar in the city. The views atop the Kimpton Journeyman Hotel are sublime, perfect for a summer evening or a winter night under the heat lamps, with a cocktail in hand and your eyes on the horizon. There’s elevated-but-not-pretentious energy, and the vibe is always on point.
7 p.m. | One More Kopp's Run
It's just that good, okay? Like a moth to a flame, like Tommy to TikTok, Kopp’s is alluring in a way that you just have to experience for yourself. Tommy's philosophy is simple: when you find places that consistently deliver, you keep on coming back. Appreciate the spots that become part of your story and the flavors you'll crave long after you've left. Get a pint to go or a milkshake to savor on your way to your next stop.
9 p.m. | Earn Your Stripes at Wolski's Tavern
End your night with a total 180 from The Outsider and head to Wolski’s Tavern. It’s one of the most Midwestern bars you'll ever experience. Friendly, welcoming, and full of character, Tommy loves this classic corner tavern for the vibe, the darts, the free basket of popcorn that pairs perfectly with an ice-cold beer and of course, the iconic 'I Closed Wolski's' sticker when you close the bar down for the night. It's a badge of honor among locals and the perfect souvenir.
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