Image of inside of 3rd Street Market Hall with people sitting at tables

Unforgettable Experiences for Couples in Milwaukee: A Local’s Guide

By: Craig

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Milwaukee, our home for over a decade and a half, is a city teeming with surprises and hidden gems, perfect for exploring as a couple.

One of our favorite things to do is to be a tourist in our own city. Over the years, we’ve found quirky experiences to serene spots tucked away in bustling neighborhoods.

We’re thrilled to share our curated list of experiences perfect for couples in this guide. Whether you’re a local couple seeking new adventures or visitors looking for a Milwaukee weekend adventure, these activities promise to add a spark to your relationship.

We also have a list of FREE things to do if you are looking for something that is budget-friendly.

Things to Do in Milwaukee for Couples

Sofar Sounds Milwaukee

Sofar Sounds Milwaukee transforms ordinary evenings into a thrilling mystery. This is because the location of their unique music events is revealed only 36 hours in advance.

Our adventure with Sofar Sounds led us to a local brewery. It was the perfect venue for an intimate music experience.

The atmosphere was cozy and inviting. That evening, we were treated to three acts, each offering a few heartfelt songs. The experience was more than just listening to music; it was about connecting with new sounds and supporting touring artists.


Smashing a beer bottle with a sledge hammer at Bust-n-Stuff in Milwaukee WI
Smashing a beer bottle with a sledge hammer at Bust-n-Stuff in Milwaukee WI

For those moments when you’re seeking an unconventional and exhilarating date, Bust-N-Stuff is the perfect destination. This unique Milwaukee spot offers a cathartic experience unlike any other.

Our visit to Bust-N-Stuff was a delightful departure from the usual dinner-and-a-movie routine. Here, we found ourselves geared up in safety equipment, ready to let off some steam. The concept is simple yet incredibly satisfying: you get to break stuff!

Amidst the sound of shattering objects, we found ourselves laughing uncontrollably. It was such a unique experience that we couldn’t help but laugh as we each smashed things.

For anyone seeking a fun and unconventional activity in Milwaukee, Bust-N-Stuff is a must-try. It’s an unforgettable way to enjoy a day or night out, offering a unique way to let loose and blast.

Reservations are necessary for this activity.

Tea Party at The Pfister

The Pfister’s afternoon tea service is an awesome experience, blending elegance with a cool, laid-back vibe. It’s like stepping into a classy, old-world setting but with a view that’s totally Milwaukee.

Our visit there was pretty unique. The Pfister is grand and impressive, making the whole tea feel more special than just regular afternoon tea. They offer many different teas and some really nice snacks, including options for those who prefer gluten-free, which is great for everyone.

The highlight? Definitely the view. Sitting up there, sipping tea, and looking out over the city is an amazing experience.

The tea service at The Pfister isn’t just about the tea; it’s about the experience of enjoying something sophisticated yet approachable, with a view that makes it unforgettable. It’s a perfect chill spot for an afternoon, especially if you want to feel a tad bit fancy.

Take a Milwaukee Tour

Image of Historic Milwaukee Walking tour. Group of people standing along the milwaukee river with tour guide

Milwaukee has some awesome tours that really show off what the city’s all about. As locals, we love going on these tours and have done several of them multiple times.

If you’re into history and cool old buildings, the Historic Milwaukee Walking Tour is perfect. And the volunteer guides are super knowledgeable and love sharing their love for Milwaukee.

For those who dig motorcycles or American culture, the Harley Davidson Museum is a must-see. It’s about way more than just bikes; it’s packed with cool stories and exhibits.

The Pabst Mansion is like a trip back in time, showing how Milwaukee’s famous beer family lived. It’s super interesting, and the mansion itself is stunning.

The Black Holocaust Museum is an eye-opener. It’s a powerful place that sheds light on African American history and experiences.

And our favorite Milwaukee tour is the Beer History Tour at Best Place. It’s a fun way to learn about Milwaukee’s beer scene, and touring the historical buildings in the Pabst Brewery complex is phenomenal.

These tours are a great mix of fun and learning, perfect for spending a day in the city.

Dine in Bernie Brewer’s Chalet

Bernie's Chalet at Lakefront Brewery
Image curtesy of Lakefront Brewery

Reserving a date night in Bernie’s Chalet has got to be one of the most “Milwaukee” things to do.

Located inside Lakefront Brewery, Bernie’s Chalet is reservable for 90-minute timeslots. Here, you and your partner will enjoy some of the best cheese curds in Milwaukee while dining in one of the most iconic relics from Milwaukee’s County Stadium. It’s a must-visit spot for baseball fans and anyone seeking a unique Milwaukee dining experience.

Whether you’re cheering for the home team or just exploring Milwaukee’s culinary scene, Bernie’s Chalet at Lakefront Brewery offers an experience that’s as memorable as it is delicious.

Indulge in a Wine and Chocolate Pairing

Image of three glasses of red wine paired with 3 handmade chocolates

If you’re looking for a romantic and tasty activity, pairing wine and chocolate at Indulgence Chocolatiers in Milwaukee is a fantastic choice.

his activity is perfect for a date night. It’s a chance to try something new and indulge in some of the finer things. Indulgence’s cozy atmosphere and knowledgeable staff make it all the more special, creating an intimate and enjoyable setting.

We spent a year living down the block from Indulgence Chocolatiers in Walker’s Point, and let’s say we stopped in quite frequently.

They have pairing classes you can sign up for, which we highly recommend (we do at least two a year). During the pairing classes, they go into how different types of chocolate complement various wines. It’s not just about tasting; it’s about understanding the flavors and what makes them click together.

They also have informal tastings you can do whenever their shop is open. We love doing this for an after-dinner treat.

Take a Cooking Class

Milwaukee offers some great spots for cooking classes, perfect for couples looking to mix up their date nights with something fun and hands-on.

One cool place to check out is the Milwaukee Public Market. They offer a variety of classes, from sushi making to Italian classics. It’s a lively atmosphere, and you get to eat what you make, which is a bonus!

Sur La Table is another great option. Their classes are super interactive and cover a wide range of cuisines. It’s a fun way to spend an evening, learning and laughing as you both try to master new dishes.

Whether you’re a cooking pro or a newbie, these classes are a great way to spend time together, learn something new, and enjoy a delicious meal that you made together.

Explore a Speakeasy

Milwaukee’s speakeasy scene is a treasure trove of unique experiences, and two spots stand out for their distinctive character and superb cocktails.

Mosler’s Vault, nestled in the confines of a former bank vault, offers an elevated cocktail experience. The ambiance, set within the sturdy walls of the old United Federal Savings & Loan bank vault, is complemented by a rotating menu of rare and intriguing ingredients. Guests can choose from different experiences, ranging from a casual 75-minute visit to a more immersive two-hour tasting adventure.

Another hidden gem is Shanghai MKE at Black Cat Alley. This speakeasy takes you back in time with its exposed brick, rich textures, and a collection of artwork and movie posters. The intimate venue serves up craft cocktails and unique spirits, providing a cozy and historic backdrop for an evening out.

These Milwaukee speakeasies offer more than just drinks; they provide a journey into the city’s past, wrapped in a modern mixology experience.

Share a Charcuterie Board at Bavette La Boucherie

Picture of charcuterie board from Bavette in Milwaukee WI

Grabbing a charcuterie board at Bavette La Boucherie was one of our favorite things to do during the pandemic. And since then, it’s become one of our favorite afternoon or early evening activities.

Bavette La Boucherie is a delightful spot for those who appreciate the finer things in a relaxed setting. It’s the perfect place to enjoy a charcuterie board, where each element is thoughtfully selected and expertly prepared.

The atmosphere at Bavette is casual yet sophisticated, striking just the right balance for a laid-back date night. Their charcuterie boards are a testament to their commitment to quality, featuring a range of cured meats, artisan cheeses, and local and exotic accompaniments.

Whether you’re a food enthusiast or just looking for a cozy spot to spend an evening, Bavette offers an experience that’s both enjoyable and gourmet. The charcuterie board, paired with a selection from their excellent wine list, is an ideal way to unwind and indulge in some of Milwaukee’s best culinary offerings.

Create Your Own Letterpress Poster

Image of the front of Bay View Printing Co in Milwaukee WI. Building is painted in bright colors; yellow, pink, purple, green

Bay View Printing Company offers a unique twist to a night out with their Drink and Ink sessions. It’s a creative haven where you can unleash your artistic side while sipping on your favorite drinks.

At Drink and Ink, couples get to dive into the world of printmaking in a fun, relaxed environment. The experience is hands-on and innovative, allowing you to create your own art pieces using traditional printing techniques. It’s not every day you get to play artist in a print shop, making this experience both unique and memorable.

The casual atmosphere and the thrill of creating something together make Drink and Ink a fantastic choice for couples. Whether you’re artistically inclined or just looking for something different to do, this activity is a great way to bond and have fun. Plus, you get to take home a piece of art.

Explore Milwaukee’s Vintage Bowling Alleys

Due to Milwaukee’s deep connection to bowling history, it has some amazing vintage bowling alleys that offer a charming and nostalgic experience.

One such gem is the Holler House, which is known for having the oldest certified bowling lanes in the USA. Playing here feels like a journey into the past, with its well-worn two lanes located in a basement. The alley oozes character and is a true representation of Milwaukee’s deep-rooted love for bowling.

Landmark Lanes, another vintage alley, offers a retro vibe that’s both cool and inviting. Its classic decor and old-school feel make it the perfect spot for a fun and laid-back night out. They also have an arcade filled with old-school games to bring you back in time.

These vintage bowling alleys in Milwaukee are more than just places to play a game. They’re spots where you can soak up the local culture, enjoy a bit of history, and have a great time doing it.

Falcon Bowl in Milwaukee, WI, represents the city’s rich bowling heritage. This vintage alley opened in 1915, and its six lanes offer an authentic bowling experience. It’s a place where locals and visitors alike can enjoy the timeless joy of bowling in a classic setting.

For a unique Milwaukee bowling experience, check out Koz’s Mini Bowl.

Koz’s mini bowl is exactly how it sounds. With miniature lanes, scaled-down pins, and human pinsetters, it offers a quirky and fun experience.

Compete Against Each Other with a Game of Shuffleboard

For couples looking for a fun and slightly competitive activity, playing shuffleboard in Milwaukee offers a great mix of entertainment and challenge. The city has some cool venues where you can enjoy this classic game.

3rd Street Market Hall is a fantastic spot to play shuffleboard for free. It’s a lively and vibrant place, perfect for those who want to enjoy the game in a bustling market atmosphere. The free access to shuffleboard tables adds to the casual, fun vibe of the market, making it a great choice for an impromptu date.

Image inside of 3rd street market hall with people sitting at tables eating

Another great venue is NorthSouth Club. Here, you can rent a shuffleboard lane and enjoy a more dedicated game experience. It’s ideal for couples who are a bit more competitive and want to focus on the game in a more exclusive setting.

Where to Stay in Milwaukee

There are a lot great hotels for couples in Milwaukee. As locals, here is where we tell our friends and family to stay when they are in town (PS. We aren’t jerks, we just don’t have a spare room for guests 😊)

  • Kimpton Journeyman – Love this one for the location in the Historic Third Ward
  • The Pfister – This one is the most famous and elegant hotel in Milwaukee
  • County Clare – Unique Irish bed and breakfast with whirlpool tubs
  • The Kinn Guesthouse Downtown or Bayview – Airbnb feel without it being an Airbnb
  • Dubbel Dutch – Great location with a boutique hotel feel

For more info: Where to Stay in Milwaukee

Where to Eat in Milwaukee

Milwaukee is a fantastic destination for foodies. With numerous restaurants and chefs being recognized by the James Beard Foundation. Milwaukee is also a diverse city where you can find excellent Mexican food as well as many other types of cuisines. Here are a few of our favorite places to grab a bite to eat.

For more info on Milwaukee Restaurants:

For more info on things to do in Milwaukee, check out these posts:

Final Thoughts of Things to Do in Milwaukee for Couples

As a couple living in Milwaukee for the past 15 years, we hope this list gives you some ideas beyond the standard Milwaukee to-do lists. These are the things that you will find us doing over and over again.

Milwaukee is a great city with so many things to do that any couple will be able to find something that sparks their interest.