Updated September 3, 2025
Let’s be honest – it’s probably been way too long since your last date night. Between hectic school nights, weekends packed with soccer games and dance practices, and an endless pile of dishes, carving out quality time with your partner can easily fall to the bottom of the list.
But a romantic night out is closer than you think! Milwaukee is full of incredible date night spots, from cozy restaurants to unique experiences that will help you reconnect.
We asked our readers for their favorite romantic things to do in Milwaukee, and they delivered. We also added a few of our own tried-and-true picks to round out the ultimate list. So consider this your sign to book a babysitter, plan a night out, and make some memories together.
Unique Milwaukee-Only Experiences
Looking for date night ideas you’ll only find in Milwaukee? These date night experiences highlight the city’s quirky charm, iconic history, and unforgettable flavors. From vintage cocktail lounges to world-class symphonies, these are the one-of-a-kind dates that truly set Milwaukee apart.
Share a Tiki Love Bowl at At Random
📍 Bay View
Step back in time at At Random, Milwaukee’s iconic retro cocktail lounge that hasn’t changed much since 1964. Cozy up in a dark booth, sip on a massive “Love Bowl” for two, or try one of their mid-century ice cream cocktails. With its vintage décor and romantic low lighting, At Random is pure Milwaukee cocktail culture.
Take a Hoan Bridge Light Show Cruise
📍 Milwaukee River / Lake Michigan
Few sights are as uniquely Milwaukee as the Hoan Bridge lit up at night. Book a river or lake cruise timed with the bridge’s dazzling light show for a magical evening on the water. (Even better? Join Light The Hoan for their annual event – it’s truly epic!) You’ll get views of the Milwaukee skyline, the glowing bridge, and the twinkling lights reflecting off Lake Michigan.
Starry Avalon Atmospheric Theater
If you’re love dinner and a movie together, you’ll want to check out the historic Avalon Atmospheric Theater in Bay View for a new twist on your classic date night. It’s one of only about 75 operating atmospheric theaters in the United States, and it’s located right on Kinnickinic Avenue near some of the best restaurants in the area. You’ll love the starry atmospheric ceiling in the theater.
Classic Romantic Date Nights
Dinner with a View at Lake Park Bistro
📍 Lake Park, East Side
Perched in a historic park pavilion overlooking Lake Michigan, Lake Park Bistro is Milwaukee’s answer to a French countryside escape. Enjoy award-winning cuisine, a romantic setting, and a post-dinner stroll through the beautiful Frederick Law Olmsted–designed park.
Share Lobster Rolls at the Harbor House.
The Harbor House is an excellent place for a romantic dinner and date night right on Lake Michigan. The Maine lobster roll is a popular choice, and the view of the lake and the downtown skyline is breathtaking.
Saint Kate / Iron Horse / Pfister for overnight romance
Entertainment & Nightlife
Live Music at Blu Bar & Lounge
The rooftop of the grand Pfister Hotel may as well be a million miles away from diaper changes and school pick-up lines. Pop a chilled bottle of champagne and be swept away with live music on Friday and Saturday nights. The view of the city is unbeatable.
Or head to the lower level of the Pfister for a shared experience at the WELL Spa. They offer a couples massage (the Doubles Relax Me package) and a Doubles Deep Tissue and Yoga Balm package.
Salsa/Bachata dancing at Freight 38.
Put your dancing shoes on, and hit up the best Latin dance spot in Milwaukee – Freight 38. Head there on a Saturday night for free lessons from local instructors.
Catch a Milwaukee Brewers Game
📍 American Family Field
Nothing says summer in Milwaukee like a Brewers game under the retractable roof at American Family Field. Grab a local craft beer, share a giant pretzel, and soak up the atmosphere.
Cheer on the Milwaukee Bucks
📍 Fiserv Forum & Deer District
The Bucks bring electric energy to downtown Milwaukee. Whether you’re courtside or up high, the vibe inside Fiserv Forum is always exciting. Make a night of it with drinks in the lively Deer District before or after the game.
Il Cervo on the rooftop of the Trade Hotel is the perfect place to stop before or after the game for drinks, garlic focaccia, house-made pasta, and the most delectable chocolate cake in the city.
Food & Drink Experiences
Spend “One Night in Bangkok” at Room Service
Looking for a date night spot that’s both stylish and delicious? Room Service in Bay View delivers an unforgettable experience with bold flavors, creative cocktails, and a lively atmosphere. Start the night with the “One Night in Bangkok” cocktail—a gin and vodka-based drink infused with coconut, galangal, chili, basil, and lemongrass. But the real showstopper? The steaming lemongrass aromatic cloud poured over the drink, filling the table with an intoxicating fragrance.
Chocolate + Wine Pairing at Indulgence Chocolatiers
📍 Walker’s Point
Elevate your sweet tooth with a visit to Indulgence Chocolatiers, where handcrafted chocolates are paired with wines, craft beers, or spirits. Sit at their pairing bar, watch chocolatiers at work, and indulge in Milwaukee’s most decadent date night.
Lakefront Brewery
The iconic 45-minute brewery tour at the Lakefront Brewery is a must-do for any Milwaukee couple, but the romantic part is outside, taking in the Milwaukee River together as you sip on your craft brews.
Arts & Culture Date Nights
Milwaukee Symphony Orchestra at the Bradley Symphony Center
📍 Downtown Milwaukee
The Bradley Symphony Center, a stunningly restored 1930s theater, is home to the Milwaukee Symphony Orchestra. Catching a live performance here combines elegance, world-class music, and a breathtaking historic setting.
Watch a Broadway Show
Across the street at the Marcus Center for the Performing Arts, you can catch a Broadway show like “Les Miserable” or “Six”. Check out the 2022-23 schedule here.
Pro Tip: The perfect spot to stay after a show at the Marcus Center for the Performing Arts is the Saint Kate -The Arts Hotel.
MAM After Dark
📍 Milwaukee Art Museum
For a livelier take on arts and culture, check out MAM After Dark at the Milwaukee Art Museum. These themed after-hours events mix music, dancing, cocktails, and full access to the museum’s galleries. It’s the perfect way to experience world-class art in a more social, playful atmosphere—great if you’re looking to combine culture with nightlife energy.
Rooftop & Patio Date Nights
Outsider Rooftop Bar
For a decidedly more modern experience, head up to the rooftop of the Kimpton Journeyman Hotel and visit the Outsider Rooftop Bar. This swanky bar is set nine stories above the trendy Historic Third Ward. Fireplace and patio lights help set the mood, and you can order cocktails, wine, and beer, plus a nice variety of shared plates and a few desserts. It’s also a great place to go for a drink after dinner if you happen to be in the area.
Reserve a Patio Table at La Dama.
La Dama in Walker’s Point (formerly Crazy Water) is home to a very romantic patio with string lights, foliage aplenty, and a trickling fountain. It’s a beautiful place to go for dinner on a warm summer night. The kitchen offers Mexican cooking with a modern twist.
Milwaukee Overnight Dates
Sometimes the best way to turn date night into something unforgettable is to make it a staycation. Here are some of the most romantic and unique hotels in Milwaukee:
Saint Kate – The Arts Hotel
📍 Downtown Milwaukee
More than just a place to stay, Saint Kate is a boutique arts destination. You’ll find curated exhibits, live performances, and even a working artists’ studio right in the lobby. Each room is uniquely designed, so no two stays feel the same. It’s perfect if you want your date night to be as inspiring as it is romantic.
👉 Check availability at Saint Kate – The Arts Hotel
The Pfister Hotel
📍 East Town / Downtown Milwaukee
Step into history at The Pfister, Milwaukee’s grand hotel since 1893. Known for its stunning Victorian architecture and world-class art collection, it’s a destination in itself. Don’t miss Blu, the cocktail lounge at the top with sweeping views of Lake Michigan and the city skyline. Guests also enjoy an indoor pool with a view, WELL Spa, classic afternoon tea service, and walkable access to theaters, restaurants, and the lakefront.
👉 Check availability at The Pfister Hotel
The Trade Hotel
📍 Deer District / Downtown Milwaukee
Located right next to Fiserv Forum, The Trade is perfect for an overnight stay after a Milwaukee Bucks game or concert. The sleek, modern rooms and rooftop views make it feel special, and you don’t even need to leave the building for a memorable meal—Il Cervo, the hotel’s Italian rooftop restaurant, is excellent for late-night dining with skyline views.
👉 Check availability at The Trade Hotel
The Iron Horse Hotel
📍 Walker’s Point
Once a 100-year-old warehouse, this hotel blends industrial style with modern luxury. It’s especially beloved by motorcyclists (Harley-Davidson Museum is just down the street), but the warm wood, leather furnishings, and intimate vibe make it a cozy spot for couples, too. Grab a craft cocktail at The Yard or curl up by the fire for a uniquely Milwaukee experience.
👉 Check availability at The Iron Horse
Hotel Metro
📍 Downtown Milwaukee
This urban boutique hotel has an art deco vibe and modern updates, making it a stylish backdrop for your overnight escape. With spacious suites, a rooftop lounge, and walkability to the city’s best dining and nightlife, it’s ideal for couples who want to mix romance with convenience.
👉 Check availability at Hotel Metro
👉 Want even more options? Check out more of the Coolest Places to Stay in Milwaukee.
Cozy Winter Date Nights Around Milwaukee
Eat dinner in a Lux Dome at Cafe Benelux.
Just down the road on another rooftop, you’ll find warm and cozy Lux Domes (only available in the winter months). The heated domes overlook the Historic Third Ward and the Milwaukee Public Market, and enable diners to have a memorable outdoor dining experience even in the cold Wisconsin winters.
Go Ice Skating at Milwaukee’s “Rockefeller Center”
The Slice of Ice ice skating rink in Red Arrow Park is in the heart of the city, and the rink is actually bigger than the one at Rockefeller Center in New York City. (That’s a fact!) The urban surroundings are upbeat and exciting, and the park is decorated with festive holiday lights in the wintertime. Popular music is amplified outside, and you can warm up together in the nearby coffeehouse, where you can rent and return your skates, sip on hot cocoa, and play footsies by the crackling fireplace.
Want more ideas? Check out all of our cozy Winter Date Night ideas around Milwaukee.
Summer Date Nights Around Milwaukee
Glide in the Swan Paddle Boats in Veteran’s Park
Glide under the stars and across the lagoon in Veterans Park in one of new LED-illuminated swan boats. Bring a blanket, because this is Wisconsin after all.
Ride the Ferris Wheel at State Fair
When you think of romance, the Wisconsin State Fair may not be the first things that comes to mind. But the magnificent Wonderwheel is the largest traveling ferris wheel in North America, and the ten minute ride offers you your own space to take in the beautiful view together. Then share a cream puff, listen to some live music, and head to the midway to win each other a giant stuffed animal.
Annual Events
Food & Froth at the Milwaukee Public Museum
If you like the Street of Old Milwaukee when you visit the Milwaukee Public Museum by day, you’ll love it even more by night. Their annual Food and Froth event allows love birds to sample wine and beer from local vendors who set up throughout the museum’s exhibits. There’s also live music in the European Village.
Milwaukee County Zoo a la Carte
The Zoo is usually where you go to show your kids hippos and giraffes, not for a romantic date night. But for one weekend a year in the summertime, the beautiful grounds come alive at night for the popular Zoo a la Carte event. You can enjoy live music and try foods from local vendors while experiencing the Zoo like never before.
Watch a Light Show in the Show Dome
For a unique Milwaukee experience, keep an eye on the Domes website and social media (also known as the Mitchell Park Horticultural Conservatory). Once or twice a year they offer at Grooving Under Glass event.
Neighborhood-Specific Date Nights Around Milwaukee
Bay View
- At Random (Tiki Love Bowl)
- Room Service (“One Night in Bangkok”)
- Avalon Atmospheric Theater
Third Ward
- The Outsider Rooftop Bar
- Lux Domes at Café Benelux
- Marcus Center for the Performing Arts (Broadway shows)
- Milwaukee Riverwalk + River Cruises
East Side
- Café at the Plaza Hotel (ivy-covered courtyard brunch)
- Shanghai Speakeasy (via Black Cat Alley — borderline East Side, but artsy vibe works for both)
Downtown
- Il Cervo
- Pfister Blu Bar & Lounge (rooftop + live music)
- WELL Spa at the Pfister
- Saint Kate Arts Hotel (overnight stay, artsy vibe)
- La Dama patio in Walker’s Point (borderline)
Suburbs
- Ca’Lucchenzo
Budget-Friendly Date Nights Around Milwaukee
Take a Walk by the Lake
No need to spend your hard-earned cash for romance. One of the best things about living in Milwaukee is our sweet spot along the shores of Lake Michigan, and you can enjoy it together anytime. For a great view, head to Atwater Beach in Shorewood, Klode Park in Whitefish Bay, or St. Mary’s Hill on the east side.
Catch a Free Concert
Summer in Milwaukee means free outdoor music almost every night of the week. Jazz in the Park at Cathedral Square, Chill on the Hill at Humboldt Park, and Washington Park Wednesdays are just a few of the favorites where you can bring a blanket, pack a picnic, and enjoy live music under the stars.
Beer Gardens
Milwaukee’s beer gardens are a low-cost way to spend an afternoon or evening together. Many allow you to bring your own picnic and games, and a shared stein of locally brewed beer is about as Milwaukee as it gets.
Festivals
From small neighborhood block parties to massive lakefront celebrations, there’s almost always a festival happening somewhere in the city during summer. Admission is often free or very affordable, and you’ll find everything from live music to cultural showcases. See our roundup of Milwaukee’s best summer festivals.
Holiday Lights Walks
Bundle up and stroll through Milwaukee’s twinkling holiday lights displays. Cathedral Square, Pere Marquette Park, and Red Arrow Park are all free to visit, and the festive atmosphere makes it feel instantly romantic. For ideas, see our roundup of all the Milwaukee Holiday Lights Displays.
At-Home Date Nights
Sometimes the best budget-friendly option is staying in. Cook a new recipe together, start a puzzle, or have a movie marathon once the kids are in bed. Browse our list of creative at-home date night ideas here.
Adventure Date Nights Around Milwaukee
Take a Helicopter Ride
For a truly unforgettable date, see Milwaukee from above on a helicopter tour. You’ll soar over Lake Michigan, the Milwaukee skyline, and even out toward scenic spots like the shoreline cliffs or countryside. It’s a splurge, but the bird’s-eye views and once-in-a-lifetime feel make it an incredible shared experience.
Kayak the Milwaukee River
For something active yet laid-back, rent a kayak and paddle together down the Milwaukee River. You’ll float past historic warehouses, riverfront restaurants, and iconic bridges, all while getting some fresh air and exercise. Many local outfitters even offer tandem kayaks so you can share the paddling.
Rent a Duffy Boat
Want the fun of being on the water without the work of paddling? Try a Duffy boat rental. These electric, easy-to-drive boats are perfect for couples, and you don’t need prior boating experience. Pack a picnic, bring along your favorite drinks, and cruise the Milwaukee River at your own pace while watching the city light up around you.
Hidden Gems
Make a Candle Together at Glassnote Candle Bar
From jasmine to lavender, and blue lotus to sandalwood, certain scents play a key role in love and romance. At Glassnote Candle Bar, you can explore these scents together and incorporate them into a special keepsake candle. The experience lasts for two hours or more, and they also offer a drink menu. It’s a unique date idea for people who like to try new things.
Sneak into the Shanghai Speakeasy
You’ll have to work a little to find this hidden gem, but it’s worth it. Make your way through Black Cat Alley on the east side of Milwaukee – a colorful space covered in murals by local artists – and ring the buzzer to get into the elusive Shanghai Speakeasy. You’ll enjoy seasonal cocktails and custom drinks, some of which are Delta-8 and CBD infused.
Brunch Dates
Cafe at the Plaza Hotel
The most romantic spot for brunch in Milwaukee is in the Courtyard at Cafe at The Plaza Hotel. It’s nestled in the center of their red brick building, covered in ivy, and it screams European vacation. Open-air seating is available for dining and drinks.
Early Morning Sweets: Head to North Shore Boulangerie for early morning tea and pastries.
Planning a romantic night out with gluten-free needs in mind? These Great Gluten-Free Restaurants in Milwaukee are perfect for date night — intimate, delicious, and gluten-free friendly.
Do have more romantic ideas? What are more fun things to do as a couple in Milwaukee? Email us at hello@mkewithkids.com.
In 2013, Calie Herbst, a former teacher with three little ones, saw a need for a “One Stop Shop” for family fun in Milwaukee. So she founded Milwaukee With Kids. Her goal was to find the best this city has to offer families and share it with other parents. In one place.
In 2019, she published “Exploring Milwaukee WIth Kids”, a comprehensive Milwaukee travel guide for families and kids.
She appears regularly on WISN News, Fox 6’s ‘Real Milwaukee’, B93.3, and Wisconsin Morning News. She has been featured in Medium, the Milwaukee Journal Sentinel, NPR, the Wisconsin Jewish Chronicle, and on CBS 58 News.
Calie is available for hosting, moderating and media appearances.
