Experience Downtown Blog

Sweet Ways to Celebrate Valentine's Day Weekend

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Downtown Milwaukee has an abundance of ways to celebrate the loveliest day of the year. From prix fixe dinners to romantic shows, even celebrations with your galentines, there's something for everyone. Explore the possibilities in our 2026 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 Amilinda
Sat, February 14
Amilinda – 315 E. Wisconsin Avenue
Celebrate with love, served the Iberian way. Savor the flavors of Portugal and Spain with a specially curated menu.

Love & Omakase
Thu, February 12 | 6pm
The Dark Room at Saint Kate – The Arts Hotel – 139 E. Kilbourn Avenue 
Escape into the warmth and intimacy of The Dark Room for an Omakase experience by renowned Sushi Chef Tou Vang designed to captivate the senses and stir the heart. Whether you're sharing the evening with someone special or treating yourself to a night of indulgence, this 14-course journey promises moments to savor.

Love in the Dark
February 13 & 14
The Dark Room at Saint Kate – The Arts Hotel – 139 E. Kilbourn Avenue
Indulge in a decadent four-course dinner in The Dark Room created by Executive Chef Heskeith Flavien, and thoughtfully paired with hand-selected drinks designed to complement each dish and elevate your celebration. Whether you're celebrating new love, a lasting connection, or simply the joy of fine dining, this unforgettable evening promises warmth, elegance, and exquisite flavor in every course.

Valentine’s Day Dinner at Bacchus
February 13 – 15
Bacchus – 925 E. Wells Street
Enjoy a three-course menu with expertly curated selections.

Hearts Above the City at Blu
February 13 – 15
Blu – The Pfister Hotel – 424 E. Wisconsin Avenue
Celebrate Valentines weekend high above Milwaukee at Blu, The Pfister Hotel’s signature cocktail lounge on the 23rd floor. Celebrate with stunning skyline views, live music, and house-made petite desserts. Enjoy an unforgettable private table experience designed for romance.

Valentine’s Day Dinner at Harbor House
February 13 – 15 
Harbor House – 550 N. Harbor Drive
Enjoy a three-course menu amid unparalleled views.

Valentine’s Day Dinner at Lupi & Iris
February 13 & 14 
Lupi & Iris – 777 N. Van Buren Avenue
Enjoy a three-course, prix-fixe dinner menu.

Valentine’s Day Dinner at Milwaukee ChopHouse
February 13 – 15 
Milwaukee ChopHouse – 633 N. 5th Street
Celebrate love at the pinnacle of downtown dining. Enjoy a thoughtfully crafted prix fixe menu or choose from a full a la carte offerings.  

Valentine’s Day Dinner at The Wolf
Sat, February 14
The Wolf – 600 N. Broadway 
Enjoy a four-course, prix fixe menu on Valentine’s Day.

Lovely Shows

A Simply Swingin’ Valentine
February 13 – 15 
Bradley Symphony Center – 212 W. Wisconsin Avenue
Cozy up with the one you love and enjoy the jazzy orchestral sounds of love and romance live on stage with vocalist Steve Lippia and your MSO. Featuring the sultry songs made popular by Nat King Cole, Frank Sinatra, Tony Bennett, and more. Take a nostalgic journey that promises to leave you tapping your toes and humming along to some of the most memorable standards ever written.

Romancing the Stars! Valentine Stargazing
February 13 & 14
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.

Just for Fun

Neapolitan Nights: A Proof Pizza Workshop
Mon, February 9 | 6:30pm
Saint Kate – The Arts Hotel – 139 E. Kilbourn Avenue 
The Proof Pizza team will guide you through this hands-on workshop with dough handling, flavor-building, and achieving that hallmark char. Enjoy a complimentary cocktail as you perfect your pie, and take home a ball of dough to recreate the experience in your own kitchen.

Galentine’s Day Celebration 
Fri, February 13 | 4pm 
the Bar at Saint Kate – The Arts Hotel – 139 E. Kilbourn Avenue
Grab your friends and kick off Galentine’s Day at the Bar at Saint Kate – The Arts Hotel with a night made for celebrating your favorite people. Dive into delicious chocolate and drink tastings, sip specialty cocktails crafted just for the occasion, and enjoy live music that keeps the energy high. It’s the perfect excuse to dress up, laugh a little louder, and make a night of it in the vibrant, art-soaked space, crowned “Milwaukee’s Best Bar To Be Seen At.”

Sweet Love: Chocolate & Wine Tasting
Fri, February 13 | 7pm
The Pfister Hotel – 424 E. Wisconsin Avenue
Enjoy a decadent evening with your special someone or a Galentine's night out with the ultimate tasting experience! Indulge in an unforgettable wine & chocolate tasting led by Executive Pastry Chef, Travis Martinez, featuring eight exceptional types of Valrhona Chocolate paired with four wines.

The Aphrodisiac Affair at Mason Street Grill
Sat, February 14 | 11am 
Mason Street Grill – 425 E. Mason Street
Discover the history and flavor of nature’s finest aphrodisiacs at Mason Street Grill. This immersive class features premium oyster and caviar tastings, shucking lessons, and the sensory secrets of these romantic delicacies. Enjoy expert pairings, including crisp rosé bubbles and signature mignonettes.

Taylor Swift Galentine’s Brunch
Sat, February 14 | 10am to 2pm
Oak Barrel Public House – 1033 N. Dr. Martin Luther King Jr. Drive
Enjoy an Eras-inspired brunch with themed cocktails, goodie bags, photo ops, and more.

Artistic Affections

A New Fashioned Love Fest 
February 12 – 15 
The New Fashioned – 1122 N. Vel R. Phillips Avenue
Enjoy an artist-led partner painting experience. Couples will each paint their own canvas—two individual works that connect into one shared piece—symbolizing unity, collaboration, and love. With guided instruction and a relaxed, welcoming atmosphere, the experience encourages laughter, conversation, and the creation of something meaningful together.
The experience begins with welcome cocktails crafted with a Valentine’s twist, setting the tone for a cozy and elevated night out. Guests can enjoy light snacks while painting, and in between brush strokes, indulge their sweet side with a sweet treat.

Valentine’s Art Tour + Portrait Class
February 13 & 14 
Saint Kate – The Arts Hotel
Sip bubbly and get creative at Saint Kate! Join us for an intimate champagne art tour led by Curator in Residence, Shane McAdams, followed by a "partner portrait" workshop where you’ll sketch your favorite person in the Artist in Residence studio with Julia Bradfish.