Whether it’s a warm July evening and your toes sink into the sand, or it’s winter and you’re bundled up in polar fleece, walking hand in hand along Lincoln Memorial Drive is a great thing to do. Along the route are little pit stops like Colectivo Coffee’s lakefront café or a custard cone at NorthPoint Custard. Bradford Beach’s revitalization in recent years means you can--during the summer months only--sip a Tiki drink under a thatched-roof hut and watch pro volleyball players slam and spike their way to a win. Don’t forget to hunt down less crowded beaches, too: South Shore Park in Bay View hugs Lake Michigan and there is a nice wooded path along the waterfront, and on the North Shore you’ll find Doctor’s Park and Schlitz Audubon Nature Center in Fox Point, and Klode Park in Whitefish Bay.
Milwaukee is filled to the brim with cozy dinner spots. This includes The Pasta Tree, on the East Side for several decades, and where couples dine on Italian cuisine in three small rooms, at a mix of small tables and banquettes. Chef-owner Suzette Metcalfe’s hearty cuisine—as Italian should be—is often sourced from local farms, and there are rotating nightly specials. And don’t forget to share a slice of Chocolate Nemesis cake. Other romantic restaurants are Lake Park Bistro on the city’s East Side in Lake Park (classic French cuisine with a wall of windows overlooking the park and Lake Michigan shoreline) and Tenuta’s (Italian entrees and pizza) in Milwaukee’s Bay View neighborhood. If both you and your date like steak, expect the royal treatment from the wait staff at Mason Street Grill, on the ground floor of The Pfister Hotel. Arrive early for live jazz in the adjacent bar. A must in the growing Walker’s Point restaurant scene—a neighborhood 10 minutes south of downtown Milwaukee—is Crazy Water, on the ground floor of a former house. Small plates and eclectic dining are what makes chef-owner Peggy Magister’s menu unique (and delicious).
Take in the Performing Arts
Milwaukee is home to a professional opera, ballet company, and orchestra, which means there’s a handful of elegant events every month to take your date to. Check out the websites for the Milwaukee Symphony Orchestra, Milwaukee Ballet, and Florentine Opera for show times and dates. Theater groups include the Milwaukee Repertory Theatre. Tucked into neighborhoods around Milwaukee are Lake Country Playhouse in Hartland, The Alchemist Theatre in Milwaukee's Bay View neighborhood, and Sunset Playhouse in Elm Grove.
You might scoff at a romantic date that involves tapping for beer, but that’s only because you haven’t been to a beer garden in Milwaukee. Within the last three years, al-fresco (open from May to October only) beer gardens have popped up around the city, and in nearby suburbs, too. Imagine sitting under an oak tree on a blanket, enjoying a picnic lunch (it’s totally fine to bring your own food, whether it’s take-out or prepared at home)—paired with Wisconsin craft beer. Among the region’s best are South Shore Park Beer Garden (with a view of Lake Michigan and the South Shore Marina) and Humboldt Park Beer Garden--both in Milwaukee’s Bay View neighborhood--and Wauwatosa’s Hoyt Park.
Before you drive out to a lesser-populated open space near the city, take the time to get a primer in stargazing (planets and constellations) from the Milwaukee Public Museum. A 22-minute guided tour--taught by an astronomy educator and with lots of opportunities to ask questions--is held at the museum on most days, included with museum admission or free for members. The University of Wisconsin-Milwaukee hosts free stargazing shows, on the Skydeck of the Physics Building, using its telescopes. Programs are also hosted at the UWM Manfred Olson Planetarium.
What Milwaukee does well are vintage bars, places that date back to the middle of last century and haven't changed a bit. Two solid examples are Bryant's Cocktail Lounge on the Near South Side and At Random in Bay View. Bryant's mixologists are so skilled there isn't a menu (although the drinks do skew into classic territory, such as Pink Squirrel, Volcano, and Old Fashioned) and at At Random you can order a Tiki Love Bowl, perfect for the first date or a milestone anniversary.