Would you believe that I first fell for Milwaukee in early January? The weather on my first trip to Wisconsin’s biggest city was achingly cold—while the lake effect is a plus come summer, in winter it’s quite the opposite—and the days were brief and grey. Yet somehow, I managed to have one of the best trips in recent memory.
Locals said if I enjoyed the city during the year’s coldest depths, how much more I’d love it come summer. Becase while most of the country is drowning in record-high temperatures, Milwaukee is enjoying blissfully mild weather.
Add to that nonstop festivals, an emerging restaurant and bar scene, a wonderfully welcoming community, and plenty of ways to pass the time, no matter your interests. No wonder Milwaukee is one of the country’s best destinations for summer vacations.
What to Do in Milwaukee
If it’s your first time in the Cream City, begin your trip with City Tours MKE’s Iconic Milwaukee City Tour. You’ll be driven around the city by a knowledgeable guide in an emissions-free electric cruiser, while learning the history of key attractions, from the Brewery District to the picturesque lakefront. Art buffs will flip for the Milwaukee Art Museum, whose stunning ship-like Quadracci Pavilion by acclaimed architect Santiago Calatrava features massive “wings” that open and close twice daily. Inside, you’ll discover 34,000-plus pieces, including an extensive selection of works by Georgia O’Keeffe.
Milwaukee lives up to its nickname of “City of Festivals” with a diverse lineup including the upcoming Milwaukee Irish Fest (August 14-17) and Mexican Fiesta (August 22-24). Situated in downtown’s historic Pfister Hotel, The Well Spa + Salon is a cozy subterranean hideaway that delivers its treatments—the massages are especially solid—in spacious suites with restrooms and showers, so you can get clean up and get dressed in total comfort. For some retail therapy, head over to Bronzeville’s Dr. Martin Luther King Drive, a thriving hub of black-owned businesses such as Angela Mallett’s HoneyBee Sage Wellness & Apothecary Cafe—a welcoming community space that doubles as a wellness cafe and retail shop—and 414LORAL, a charming floral studio that hosts a BYOBouq (build your own bouquet) flower bar every Saturday.
Where to Eat and Drink in Milwaukee
Located in Milwaukee’s Lower East Side, Birch fits the bill for every occasion. Overseen by James Beard-nominated chef Kyle Knall, the lively restaurant anchored by an open kitchen and roaring wood-fired oven features ever-rotating dishes spotlighting ingredients sourced from area farms such as Jerry’s Produce, Cindy’s Greenhouse, and Centgraf Farms. (A highlight from a recent meal, for example, included a pretty plate of rosy steelhead trout tartare accompanied by verdant perilla leaves.) The wine list, curated by general manager and sommelier Jeff Cleveland, enlists an equally considered approach with a strong showing of small producers and low-intervention wines.
Lupi & Iris by James Beard Award-winning chef Adam Siegel sends out refined Mediterranean fare (think: grilled Spanish octopus, dover sole with persillade sauce, housemade lemon trofie) in a light-flooded dining room accented with a wavelike ceiling and azure-blue seating. Part of The Bartolotta Restaurants, Harbor House marries serene waterfront views with globally-inspired seafood dishes from raw West Coast oysters, to Maryland blue crab cakes, to South African lobster tails. And no visit to town would be complete without trying Milwaukee-style pizza, crispy-thin pies smothered with edge-to-edge toppings. For some of the best, head to Zaffiro’s, a local institution that’s been around since 1954.
Tucked away within the Dubbel Dutch Hotel is Agency, Milwaukee’s coolest place to throw back drinks. The ambiance of this watering hole is cozy—you really feel like you’re hanging in someone’s quirky home—and its mission of inclusivity is special. So everyone can get in on the fun, a non-alcoholic version of every cocktail on the menu is available. (No wonder Agency was a 2025 James Beard Award for Best New Bar finalist.) At Milwaukee’s oldest bar, Bryant’s Cocktail Lounge, the talented bartenders whip up drinks based on your preferences—reportedly, they’re able to make up to 600—and not from a menu.
Where to Stay in Milwaukee
Taking up residence in a towering 1927 Art Deco structure is Hilton Milwaukee. Well-suited for all kind of travelers, from business to families, the downtown property blends history—it’s a member of the Historic Hotels of America—and modern comforts, including several restaurants and bars, a fitness center, and thanks to the just-unveiled first phase of a sweeping $40 million renovation, 554 airy guest rooms and suites accented with pale blue curtains, custom art, and marble sinks in the bathrooms. The next phase will refresh the common areas, like the stunning two-level lobby, and meeting spaces.