Experience Downtown Blog

Love is in the Air: Downtown Milwaukee's Guide to Valentine's Day

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Love is in the air and Downtown Milwaukee has an abundance of ways to celebrate the loveliest day of the year. From prix-fixe dinners to romantic flicks and artistic affections, there's something for everyone. Explore the possibilities in our our 2025 Valentine’s Day Guide. But don't delay in locking in plans. Many of these offerings require reservations and have limited seating.

Romantic Dinners

Valentine’s Day Dinner at ARIA
February 14 & 15
ARIA – 139 E. Kilbourn Ave. 
Celebrate Valentine's Day with an enhanced menu of artisanal selections. Reservations can be made by calling 414.270.4422 or visiting OpenTable.com.  

Valentine’s Day Dinner at Bacchus
February 14 & 15
Bacchus – 925 E. Wells Street
Enjoy a three-course menu with expertly curated selections.

Valentine’s Day Dinner at Harbor House
February 14 &15
550 N. Harbor Drive
Enjoy a three-course menu amid unparalleled views.

Love in the Dark
February 14 & 15 | 5:30pm & 8pm
The Dark Room at Saint Kate – The Arts Hotel – 139 E. Kilbourn Avenue 
Delight in a decadent four-course dinner, expertly paired with hand-selected drinks to elevate your celebration with someone special.

Valentine’s Day Dinner at Lupi & Iris
February 14 & 15
Lupi & Iris – 777 N. Van Buren Ave.
Enjoy a three-course, prix-fixe dinner menu, with an option to enhance your dining experience with an in-house floral arrangement for your table. 

Valentine’s Day Dinner at Mason Street Grill
February 14 & 15
Mason Street Grill – 425 E. Mason Street
Indulge in an exquisite four-course dinner and raise a toast to your special someone with a complimentary glass of bubbles. 

Valentine’s Day Dinner at Milwaukee ChopHouse
February 14 & 15
Milwaukee ChopHouse – 633 N. 5th Street
Enjoy an exclusive four-course Valentine's dinner menu designed with elegance, luxury, and unforgettable memories in mind.

Lovely Shows

Casablanca: Film with Orchestra 
February 14 – 16
Bradley Symphony Center
Experience one of classic Hollywood’s most romantic tales on the big screen with live orchestral accompaniment as Milwaukee Symphony Orchestra performs Max Steiner’s Oscar-winning score live in sync with the iconic film. 

Romancing the Stars! Valentine Stargazing
February 14 & 15
Milwaukee Public Museum
Embark on an out-of-this-world date! Take a romantic tour of the universe to explore the magic of night and constellations of love.

Florentine Opera: Acis & Galatea
February 14 – 16
Marcus Center for the Performing Arts – Wilson Theater at Vogel Hall
Handel's beloved Acis & Galatea weaves a tale of love, jealousy, and mythological mischief. Director Meeker dubs it "visual poetry" as a shepherd's love for a sea nymph is disrupted by a cyclops, and a lover's tragic murder brings fountains of resolution to heartbreak.

Artistic Affections

For the Love of Art
February 14 & 15 | 5pm 
Saint Kate – The Arts Hotel
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 special someone will join other art lovers to be immersed in the creative process and learn about internationally acclaimed artists such as Mickalene Thomas and Damien Hirst and Milwaukee-based artists such as Jason Yi, Michelle Grabner, and John Riepenhoff. 

Ephemeral Love: A Valentine’s Workshop
Saturday, February 15 | 3pm to 6pm
The Arc Theatre at Saint Kate – The Arts Hotel 
Step into a world of nostalgia and creativity with a mixed-media workshop with Artist in Residence Megan Woodard Johnson. Inspired by vintage ephemera, photographs, and mementos, guests will be guided through the art of storytelling on canvas. Whether you’re a seasoned artist or a beginner, this workshop invites you to tap into your creative spirit, celebrate love in all its forms, and leave with a one-of-a-kind keepsake to cherish for years to come. 

Other Sweet Activities

Sweet Love: Chocolate & Wine Tasting
Saturday, February 8 | 7pm to 9pm
The Pfister Hotel – Rouge Ballroom
Indulge in an unforgettable experience as you sample eight exceptional types of Valrhona chocolate, widely regarded as some of the finest in the world. Throughout this exclusive event, guests will explore a curated selection of chocolates, each offering unique flavors and nuances, expertly paired with four distinct wines.  

Counter Cooking Class for Couples
Saturday, February 8 | 11:30am 
Mason Street Grill – 425 E. Mason Street 
Learn from Mason Street Grill’s Executive Chef as you sip on bubbles and create your own delicious three-course meal. Don’t miss this hands-on culinary adventure. 

Heart-Shaped Cakes to Order
February 13 & 14
The Pfister Hotel
Sweeten your Valentine’s Day with The Pfister’s heart-shaped cake! This show-stopping dessert features vanilla cake, champagne syrup, fresh raspberries, vanilla mousse and buttercream. Pre-order in person at the barista counter at The Pfister Cafe, or online. Order pickup between 6am and 3pm on Thursday, February 13 and Friday, February 14.

Ice Skating at Red Arrow Park
Ongoing, weather permitting
Red Arrow Park
There’s nothing sweet than gliding hand in hand amid the picturesque backdrop of Downtown Milwaukee. Bring your own skates and skate for free, or rent a pair. Skates are $11 for adults and $8 for youth 17 and under.