A guide to Milwaukee: Where to eat, drink, play and stay

When you want a truly unique cocktailing experience, there’s no better place in town than Bryant’s. Mixing up drinks and clever conversation since 1938, this no-reservations spot has a seriously deep catalog of cocktails (we’re talking north of 400) and is known for, among many others, its Wisconsin brandy Old Fashioned and array of ice cream cocktails, like the Pink Squirrel, which was created here. This dark and swanky spot takes you back to a simpler place in time with a focus squarely on enjoying cocktails. Go for happy hour Sunday through Thursday for $5 specials. Then go visit sibling bars At Random and The Estate.

1579 S 9th St, Milwaukee, WI 53204

The brewery, which actually sits on the Milwaukee River and not Lake Michigan a few blocks away, has been pouring some of the city’s best brews since 1987. Go by for a pint, a meal and a tour, which lasts 45 minutes and includes four eight-ounce pours. In warmer months, grab a table outside along the water. This organic-certified brewery offers a Friday fish fry—polka included.

1872 N Commerce St, Milwaukee, WI 53212

Goodkind has been leading Milwaukee’s modern cocktail charge since 2015 and its ever-changing drink list, which often highlights seasonal Midwestern ingredients, is as interesting and diverse as its dining menu. Belly up to the long wood bar set below a vintage tin ceiling for the classic spicy crab pasta or smoked whitefish tartine. Wash those down with a glass of the winter sangria, a mushroom Mai Tai or a Quebec cocktail with Four Roses bourbon, Rittenhouse rye, Fernet, maple syrup and lemon. It's like a cozy hug in a glass.

2457 S Wentworth Ave, Milwaukee, WI 53207

From the team behind Bittercube Bitters, Mosler’s is an intimate speakeasy cocktail bar housed inside the former United Federal Savings & Loan bank vault—a property dating back to 1949. Soak up the history with a rotating and creative cocktail list featuring spirits ranging from barrel-proof Puerto Rican rum to a house blanco tequila blend, and eclectic ingredients like celery syrup, tamari and Bittercube’s host of bitters.

5900 W North Ave, Milwaukee, WI 53208

This is the city’s premier museum and the wow factor starts before you even enter the building overlooking Lake Michigan. Designed by Santiago Calatrava, the modern white concrete and glass building sprouts wings at various points throughout the day, which is truly a sight to behold. The collection includes 25,000 works of art by the likes of Georgia O’Keeffe, Rodin, Degas, Monet, Warhol, Picasso, Miró and many more dating back to the 15th century.

700 N Art Museum Dr, Milwaukee, WI 53202

With four main themes set across the museum—remembrance, resistance, redemption, reconciliation—the museum aims to highlight the often-dark history of Black people in America. The ABHM covers historical events stretching from the African slave trade through modern times and tells stories of injustices, redemption and forgiveness. The museum now sits in the historic Bronzeville neighborhood following the 2022 reopening after it received a $10 million anonymous donation. The museum also hosts a 3,200-page virtual museum to continue the journey long after your visit.

401 W North Ave, Milwaukee, WI 53212

Set across 10 blocks, the Historic Third Ward is Milwaukee’s arts district with galleries, shops, restaurants and entertainment. Plan a day to meander and browse and be sure to include a chunk of time to wander through the Public Market. This vast hall, which opened in 2005, features numerous independent stalls offering everything from wine, barbecue, poke and smoothies to coffee, seafood, baked goods and meats and cheeses. Retail shops throughout the Third Ward include local men’s and women’s boutiques, housewares, specialty stores and more. In addition to wandering about the historic buildings, the Third Ward also sits adjacent to the Riverwalk and Lakeshore State Park.

400 N Water St, Milwaukee, WI 53202

If you’re a fan of the open road and classic hogs, this is a must stop when you visit the Cream City. Harley-Davidson started in Milwaukee in 1903 and quickly became an iconic American brand. The museum showcases hundreds of motorcycles, even dating back to the earliest days. You’ll see classic bikes and even one that survived a ride across the Pacific Ocean following a tsunami in Japan that swept it away. With bikes, memorabilia, signage and more, this is a one-of-a-kind experience for a Harley lover.

400 W Canal St, Milwaukee, WI 53201

Before you pop in for a meal at The Diplomat, pad in an extra 20 minutes (or more) to browse this fantastic Italian market, which has operated in the area since 1946. You can get fresh and dried pasta, gorgeous charcuterie, imported olive oil and balsamic vinaigrette, risotto, dried herbs, chocolates, sauces, Italian wine and so much more. Even if you don’t buy anything (which, frankly, why wouldn’t you?), it’s just a cool place to browse the beautiful products. If you’re in the mood to broaden your culinary skills, Glorioso’s offers classes to teach you how to make pizza, steaks, shrimp scampi, chicken marsala, ravioli and more. 

1011 E Brady St, Milwaukee, WI 53202

Steps from the Harley-Davidson museum, this 100-year-old, dog-friendly, loft-like property is a motorcycle fan's dream. The oversized suite-sized guest rooms have a rebel edge with leather-covered headboards and benches, exposed brick and wood beams. And while you will want to explore the city’s vibrant dining scene, you almost don’t have to leave the property. From the hearth-driven Ash (with a four-course wagyu beef tasting menu) to lobby pub Branded to the seasonal outdoor Yard, options abound here. On-site motorcycle parking included, of course.

500 W Florida St, Milwaukee, WI 53204

There’s no better way to experience the Historic Third Ward than by staying right in the heart of it. This modern nine-floor, pet-friendly boutique hotel has 158 guest rooms and suites with views stretching out over the city. Rooms are outfitted with plush bedding with Frette linens, local artwork, yoga mats and modern bathrooms boasting walk-in showers and free-standing tubs, and some have living areas with deep lush couches. The common areas feature fireplaces and plenty of cozy seating to kick back. Want an even better view? Pop upstairs to rooftop bar The Outsider for cocktails no matter the weather. Or book a meal at Tre Rivali for Mediterranean-inspired fare.

310 E Chicago St, Milwaukee, WI 53202

Stepping into the centrally located theater district property (with a complimentary glass of bubbles, of course), you’ll wonder if you walked into a modern art museum complete with rotating exhibits or if this really is your uber-cool hotel. With contemporary art throughout the public spaces and guest rooms, this property is a gallery within itself. The Saint Kate offers 219 apartment-like rooms, including four specialty suites designed by local artists, and comfortable pet-friendly accommodations. Music plays an almost equal importance, with turntables and a selection of vinyl and ukuleles in each room. So spin a disc and kick back in your living area after pampering yourself in the oversized walk-in showers with spa-style products.

The hotel boasts five on-site restaurants and bars: the ground-level Proof for Neapolitan-styles pizza; The Bar, off the lobby, for all-day dining and drinking; the contemporary American Aria with attached Champagne and wine bar, Giggly, on the second floor; and the supper club-vibed The Dark Room, bookable for private events up to 25 people. When it comes to chic, unique hotels, it doesn’t get better than this.

139 E Kilbourn Ave, Milwaukee, WI 53202