Whether you’re on the hunt for Valentine’s Day ideas or a random Tuesday evening, consider this your cheat sheet to romance in the Good Land. Check out these eight great date ideas with a Cream City twist!

 

Marcus Performing Arts Center Stage

 

Dinner and a Show in the Milwaukee Theater District


Food, entertainment and quality time with someone you, like, like-like. What’s better than that? In the Milwaukee Theater District, you really can have it all, with restaurants just steps from the collection of theaters downtown.
 

From the age-old tale of star-crossed lovers, “Romeo and Juliet,” at Skylight Music Theatre and the Milwaukee Rep, and the irreplicable energy of live music at a Pabst Theater Group venue like Trampled by Turtles at the Pabst Theater and Colter Wall and Friends at the Miller High Life Theatre, to the lush sounds of the Milwaukee Symphony Orchestra at Bradley Symphony Center, there’s something perfect for you and your date, too!
 

Before you raise the curtains on romance and fill your soul with the evening’s entertainment, make plans to fill your stomach at a nearby restaurant. Our recs?
 

At the nexus of the Milwaukee Theater District, you’ll find this restaurant. Located on the second floor of Saint Kate – The Arts Hotel, it offers a menu of playful, artisanal American cuisine.
 

As seen on “Top Chef: Wisconsin,” at this restaurant, the flavors of the French and Italian Riviera come together to form an unforgettable dining experience in the sleek dining space.
 

Step into the life of luxury. Ensconced in textured wood and carved rock, the intimate dining room offers some of the city’s finest steaks under ambient mood lighting.
 

Check out a restaurant run by a James Beard-recognized chef, where the flavors of Spain and Portugal combine to create a dining experience you’ll never forget.
 

Perched high above the city atop The Trade Hotel in Deer District, this dining destination offers traditional Italian dishes with views of the cityscape second to none.

 

person eating indian food

 

A Romantic Meal

Maybe a night at the theater isn’t your thing. Perhaps you’d prefer to skip the theatrics and head straight for a romantic dinner that’d make any foodie green with envy. Here are some restaurants where you can kindle the spark of romance with some sparkling conversation in the inviting ambiance of a restaurant’s dining room. Here are just some places to impress that special someone.
 

The creation of James Beard-recognized chef Kyle Knall offers a slate of ever-evolving seasonal dishes that celebrate the flavors of the Midwest.
 

Tucked away in the Bay View neighborhood, here, you’ll find a modern approach to old-world dining.
 

The longtime restaurant within a restaurant has found a home in Bay View. Run by “Top Chef: Wisconsin” finalist Dan Jacobs and James Beard-recognized chef Dan Van Rite, the restaurant offers a rotating, globally inspired menu.
 

If the date calls for fresh seafood with even fresher skyline views, this is the place to be. Run by The Bartolotta Restaurant Group, for 15 years, the restaurant has offered one of the city’s premier lakefront dining experiences.
 

A reimagination of the modern butchery by James Beard-recognized chef Karen Bell, this restaurant has flourished as a full-service restaurant with a farm-to-table focus on sustainability.
 

Traditional Indian cuisine with a modern twist. With walls of Cream City brick, the intimate dining space is perfect for a romantic night out.
 

Over on Brady Street, this restaurant is the vision of Chef Dane Baldwin, winner of the James Beard Foundation’s “Best Chef: Midwest” in 2022. The restaurant brings approachable fare in a shareable format.
 

Translating to fire and ice in old Norse, this restaurant is just the place to turn up the heat on romance for date night.

 

Oriental Theatre

 

Movie Night

Milwaukee’s historic theaters, including The Oriental Theatre and the Downer Theatre, are so much more than just cineplexes; they’re an experience of their own. Revel in the warm ambiance as you and your boo experience the drama, the action, the wild spectacle of the theater side-by-side on the big screen. More info:
 

For a movie-going experience second to none, head to this East Side staple. Open for nearly a century, the theater’s ornate touches, detailed murals and over 100 (yep, you can count ‘em!) elephants elevate your night out at the theater to a cinematic evening all its own.

 

Once Milwaukee’s oldest operating theater, for 110 years, this city landmark is an intimate venue to catch a flick.

 

198591-vm_redarrowparkiceskating_3

 

Ice Skating

Your favorite part of your favorite rom-com! Instead of going to the movie, step into a cinematic scene of your own making with an evening of ice skating under the stars. Lace up your skates and gracefully glide across the sheet of ice with your partner. Or, you know, laugh at each other as you desperately try to keep from wiping out. The choice is yours! Here are a few ideas:

 

This rink offers skate rentals, cityscape views and an oval that’s larger than The Rink at Rockefeller Center, all in the heart of downtown.

 

Just a few minutes from downtown, Lake Park’s ice rink is a peaceful respite from the hustle and bustle of life. The two of you can slide across the ice with the park’s many trees and wide-open spaces as a backdrop to your own Hallmark moment.

 

The proving ground for U.S. Olympic hopefuls from across the country for the past 33 years, but you don’t have to be an elite speedskater to gracefully coast across the ice center’s Olympic oval. Located indoors, the Pettit is perfect for skating in any weather, with open skating sessions available year-round.

 

198856-vm_summer22_hdnickcollura_shanghai_87

 

Drinks

It’s a go-to first date idea and the perfect way to start (or finish) a night out for couples at any stage. A cocktail in a bar with just the right ambiance can make all the difference. Whether it’s a brew with a rooftop view or a chardonnay in a hideaway, here are some bars to match the vibe:
 

Atop The Kimpton Journeyman Hotel, this space is a swanky location for cocktails, with fire pits to cozy up to one another.
 

A slice of time, this bar in Bay View offers mid-century ice cream drinks, classic cocktails, and more in a vibey space that is perfect for dates.
 

 Named after the American frontiersmen, here you’ll find a menu that caters to the adventurous palettes of the modern imbiber.
 

A speakeasy tucked away in Black Cat Alley, specializing in Absinthe. Walk-ins are on a first-come, first-served basis, so be sure to reserve your spot ahead.
 

Perched above the Milwaukee River, you can take in spectacular city views with a craft cocktail in your hand.
 

Explore a massive menu of tea and non-alcoholic cocktails that are both good and good for you.
 

Welcome to the nation’s first fully hybrid cocktail bar. Located inside the Dubbel Dutch Hotel, every drink has both an alcoholic and a non-alcoholic version.

 

Located right across from Cathedral Square Park, this bar’s bright, upscale look is perfect to kick back and sit at the bar. Plus, just in time for Valentine’s Day, the wall of neon hearts has returned, each with its own heartfelt pun.

 

one person bowling in front of their friends in a dimly lit bowling alley

 

Game Night

A little friendly competition never hurt anyone! Okay, that’s not totally true, but for couples looking to bond, you can’t go wrong with a game night. More than dinner or drinks, activities like these offer you and that special someone the opportunity to connect over a shared passion or learn something entirely new together. That, and the ultimate bragging rights when you win. Anyways, here’s where to go to prove that you’re the ultimate champion or, alternatively, have a blast with your partner.
 

Indoor mini-golf, made your way! Set up your hole, then see what other teams have in store for you as you play a nine-hole round.
 

Shuffleboard or axe throwing? The easy breezes of the tropics or the flannel-clad chill of the Northwoods? Or maybe both? Cross the equator by crossing the bar.
 

You’ve played plenty of darts, but how about taking a swing at axe throwing?
 

Shuffleboard, pinball, ping pong and Nintendo wall?! Yep, this food hall has it all and more, with vendors and a massive bar.
 

  • Bowling

A Milwaukee tradition unlike any other, at Holler House, you can roll a few frames at the country’s oldest-sanctioned bowling alley.
 

Maybe you’re more of a pinball wizard than a pure athlete. That’s great! You and your special someone can challenge each other at all of your favorite arcade games.

 

198904-vm_glassnotecandlebar-01

 

D-I-Y Date

For creative couples looking to make magic, memories and a little memento to take home, this one’s for you! Maybe you’re the next Van Gogh, maybe you’re the next Warhol or maybe you’ll smash a whole bunch of plates. You just never know! From pottery painting to candle making, here are some places to go for romantic inspo:

 

It’s rare that a paint and create studio encourages you to make something that you eventually burn, but here, it actually makes sense. Select your scents, colors and wax as you make your very own candle to take home.
 

Screen printed posters made by you? This is your next stop. The print shop’s drink and ink events allow you to create your own letterpress posters, letting your creativity thrive as you imbibe.
 

Practical and creative, you get to select a piece of pottery to paint and eventually take it home with you. Now, whether you want to paint a pot or a fox figurine that’s entirely up to you. No judgment here!
 

While all of these other D-I-Y dates are messy, at this stop, you’re encouraged to make a mess! Bash as much as you as you demolish everything in your wake as you break things and make memories together.

 

rows of shelves and tables of books

 

Coffee and a Bookstore

Don’t sleep on daytime dates. These remarkably underrated meetups can be just as romantic as their nighttime companions, offering even more ways to connect. One of the perfect day dates, or daytes if you will, is the coffee shop and bookstore pairing. Cozy up with your favorite caffeinated beverage as you get to know each other, then head over to a local bookstore to find your next read as you rove the aisles and dig into your partner's interests.

A match made in Milwaukee, a local coffee chain meets a beloved bookstore on the city’s East Side.
 

More than coffee, you can also savor a mochinut at this stop. Similar to a donut, a mochinut is a bit chewier with a slight difference in flavor. Grab your coffee, your sweet treat and roam the two-story bookstore next door.
 

Meander through the stacks and stacks of used books and find your next read. Then, head just a few blocks away for a coffee or maybe even lunch if the date goes well!

 

198169-vm_potawatomi_dreamdance-steakhouse_md_35
 

Valentine’s Day Events

We’re just getting started! Looking for plans to make Valentine’s Day special this year? From intimate cooking classes to elegant prix-fixe dinners, we've got everything you need to create an unforgettable celebration. Found something that catches your eye? Don't wait—these romantic spots fill up fast, so make your reservations today.

Valentine's Day at Explorium Greendale Feb 15

Valentine's Day at Explorium Greendale

🍫❤️Valentine's Weekend Sweet Treats at Explorium! Join us at Explorium for a weekend full of love, warmth, and delicious delights! From Friday, February 14, through Sunday, February 16…

Valentine's Day at Explorium Third Ward Feb 15

Valentine's Day at Explorium Third Ward

🍫❤️Valentine's Weekend Sweet Treats at Explorium! Join us at Explorium for a weekend full of love, warmth, and delicious delights! From Friday, February 14, through Sunday, February 16…

Valentine's Day at Shanghai Speakeasy Feb 15

Valentine's Day at Shanghai Speakeasy

Celebrate Valentine’s Day with timeless elegance at Shanghai Speakeasy. Whether you're sharing the evening with a partner, or friends, or treating yourself, indulge in a curated…

Valentine's Pop Up Event Feb 15

Valentine's Pop Up Event

We are hosting a Valentine's Pop Up Event on Saturday February 15th from 12-5pm at our Triple Taproom! Shop with local maker's & artists, make your Valentine's Day cards (for free!)…

Casablanca: Film with Orchestra Feb 15

Casablanca: Film with Orchestra

CONCERT DETAILS “Of all the gin joints, in all the towns, in all the world, she walks into mine.” Walk into Allen-Bradley Hall Valentine’s weekend and experience one of classic…

For the Love of Art Feb 15

For the Love of Art

Enjoy an intimate, dynamic tour of the art collections and feature exhibitions on display over a glass of bubbly with Saint Kate's Curator in Residence, Shane McAdams. You and your…

Martini Flights & Chocolate Pairings Feb 15

Martini Flights & Chocolate Pairings

Step into a world of refined flavors with a mini flight of exquisite martinis and decadent chocolate delights. Sip on the bold richness of Central Standard's Espresso Martini, the silky…