Top Milwaukee Private and Luxury

Milwaukee is known for its beer, brats, baseball, and lakefront scenery, but it offers much more than most travelers realize. Learn about the city through the eyes of a resident guide on this Milwaukee sightseeing tour, see famous attractions, trendy neighborhoods, an art-filled alley, and so much more—including a bronze statue of the Fonz of “Happy Days” fame.

Swap the big bus tours for a crowd-free experience. Traveling in an open-air, five-seater electric vehicle, you'll thoroughly explore the historic city of Milwaukee, from popular tourist destinations to some hidden gems that most visitors miss. As you travel, your guide will fill you in on Milwaukee's rich and exciting history. This tour has different lengths to suit your schedule.

The Midwestern city of Milwaukee is known for its beer and cheese and this walking food tour gives you a taste of the best. Join a small group and enjoy a walk through "Brew City" to sample a number of beers and regional snacks. Learn about the 19th-century Germanic population that immigrated to the area and its influence on today's local cuisine.

The Milwaukee Downtown ride takes you on a on an exhilarating helicopter journey down the Milwaukee Bay where you can witness Downtown Milwaukee like never before! This ride offers a truly unique perspective, soaring directly over the heart of the city. You’ll be treated to sweeping views of the Milwaukee River, the iconic Hoan Bridge, and the majestic Milwaukee Art Museum. But that’s not all – this ride encompasses the entire cityscape, ensuring you don’t miss a single landmark.

Unveil the dark history of Brew City with this ghost tour of the city’s most haunted locations. Meet your guide for a ghoul-fueled stroll through the heart of Milwaukee to take in spirit-infested historic hotels, theaters, and even skyscrapers. Be entertained by bone-chilling ghost stories and tales of paranormal activity as you delve into Milwaukee’s ghoulish past.

As seen on BBC, NBC, and featured on Netflix’s Dark Tourist, this is one of the most talked-about true crime tours in the world. The Cream City Cannibal Tour explores one of Milwaukee’s most infamous criminal cases—walking through the exact neighborhood where multiple events connected to a notorious serial killer took place. This is not a casual history tour. Through guided storytelling, guests are led through the psychological, cultural, and real-world impact of the case, offering insight into how it unfolded and why it continues to be studied today. The tour has even been referenced in academic settings, including university psychology and criminal justice programs. Expect a deeper, more intense experience—focused on understanding, not sensationalizing. Outdoor tour. Rain or shine. Not recommended for those sensitive to true crime content.

Explore Milwaukee’s criminal underworld on the Mobsters and Mafia Tour, a guided walking experience that uncovers the rise and fall of the Milwaukee Mob and the powerful Balistrieri crime family. Visit historic locations while discovering how organized crime, political influence, and underground enterprises shaped the city throughout the 20th century. Hear captivating stories of power, loyalty, corruption, and betrayal as your guide reveals the real people and events behind one of Milwaukee’s most fascinating chapters. While the tour touches on the city’s Prohibition-era roots, its primary focus is the Milwaukee Mob and the figures who dominated the city’s underworld from the 1960s through the 1980s. Perfect for history enthusiasts, true crime fans, and curious travelers seeking a side of Milwaukee few visitors ever discover.

Kick off your morning with a guided e-bike tour around Milwaukee. Covering about 15 miles, you’ll ride through historic neighborhoods and scenic parks, with stops including the North Point Lighthouse and Villa Terrace Museum and Gardens. Capped at eight for a personalized experience, this tour is a fun, active way to pack in plenty of sightseeing. Hear facts and insights from your guide along the way.

Milwaukee is called many names; Brew City, City of Festivals, and Cream City, but it is most recognized as the place for great beer and cheese in the Upper Midwest. The large 19th century Germanic population continue to influence our local food products and dishes while some of the best restaurants from the historic Third Ward to East Town Downtown. When booking our winter exclusive Skywalk Food Tour you'll get to experience and enjoy all the best we have to offer from a warm second-story perspective. You'll get to experience and enjoy all the best we have when you book our Secret Food Tour: Milwaukee. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Milwaukee is a city shaped by its waterways, its waves of immigrants, and its bold spirit-famous for its German heritage, its brewing traditions, and its knack for reinvention over nearly two centuries. Our journey today starts at Wisconsin Historical Marker three three three, which marks the heart of old Kilbourntown, walk through stories of rivalry, resilience, and remarkable change, all the way to the bustling Milwaukee Public Market in the Historic Third Ward. Go at your own pace. The tour never expires. This is a hand free experience, press play and put your phone in your pocket. The tour is location aware, and plays as you walk. It never expires.

One of the most haunted bars in the nation, Shaker’s Cigar Bar—a Milwaukee institution formerly owned by the infamous Al Capone—has a history as wild as its ghostly encounters. On this small-group tour, explore behind the scenes, hearing stories about its Prohibition-era connections, the bar's cemetery and brothel past, and accounts of lingering spirits. Part history tour, part paranormal experience, this tour is not for the faint of heart.

Milwaukee is chock-full of epic holiday light displays, and you’ll get to see—and snap—them all on this hop-on hop-off tour. Great for locals and visitors, you’ll cruise from Catalano Square to Pabst Brewery and more, only getting off when you like. Along the way, expect caroling, a complimentary drink and dessert, and plenty of glowing Christmas cheer.

Get to know some of the darker corners of Milwaukee’s history on this small-group walking tour of the city’s downtown. You’ll enjoy hearing haunting tales associated with famous Milwaukee landmarks like the Pfister Hotel, City Hall, and the Pabst Theater as your guide leads you through the Cream City evening.

Explore the Immigrant, Labor, and Civil Rights History of Bay View through a gentle walk in this charming neighborhood of Milwaukee. Emeritus History Professor Tim Thering will transport you back to three different time periods that dramatically shaped the Bay View neighborhood, the city of Milwaukee, and the nation. You will learn about the Bay View Massacre that tragically ended Milwaukee’s immigrant workers’ struggle for the 8-hour day. You will hear about how Anarchist Italian immigrants in the neighborhood battled with local authorities during World War I. Finally, you will discover how the son of Bay View grocers, Father James Groppi, helped to lead the Milwaukee Civil Rights movement of the 1960s. The tour includes visiting several iconic businesses in this tightly packed corner of Bay View, Milwaukee. Food and most drinks are included in the price.

Step back into Milwaukee’s Prohibition era and uncover a world of speakeasies, madams, gangsters, corruption, and scandal. The Whorin’ 20s Walking Tour explores the city’s notorious vice district during the Roaring Twenties, when bootleggers, brothel owners, politicians, and organized crime figures helped shape Milwaukee’s nightlife and underground economy. Led by expert storytellers, this entertaining and historically grounded walking tour reveals the hidden stories behind the city’s most colorful characters and forgotten locations. Along the way, guests will discover how Prohibition transformed Milwaukee and why the era continues to captivate visitors nearly a century later. Perfect for history enthusiasts, groups, couples, bachelorette parties, and anyone looking for a different side of Milwaukee beyond breweries and ballgames. Bride goes free with qualifying bachelorette party reservations.

See more of Milwaukee in less time—and give your feet a rest—on this exciting E-bike tour. After getting settled on your bike and joining a small group, cruise around the city to sights including Walker Square, Milwaukee Pierhead Lighthouse, Bradford Beach, and more. Cover more ground than you could on foot as you zip between top landmarks, enjoying a fun and effortless way to experience the city.

Experience the sweeter side of Milwaukee on this fun and family-friendly walking tour through one of Wisconsin's most vibrant cities. Along the way, you'll enjoy a delicious assortment of donuts, pastries, and locally inspired sweet treats from some of Milwaukee's favorite bakeries and cafés. As you explore downtown, your guide will share fascinating stories about the city's rich history, impressive architecture, thriving arts scene, and unique local culture. You'll discover iconic landmarks, hidden gems, and neighborhood favorites while enjoying some of the best sweet treats Milwaukee has to offer. Whether you're visiting for the first time or are a lifelong local, this tour is the perfect blend of delicious food, local history, and unforgettable memories.

With 191 different blocks, it should come as no surprise that Milwaukee is known as a ‘City of Neighborhoods’. On this self-guided walking tour, you’ll be introduced to two of its most interesting suburbs, Brady Street and the Lower Eastside, and their architecture. You’ll begin by discovering the impact that Polish and Italian immigrants had on Brady Street Historic District, including delicious Italian cuisine at Sciortino’s Bakery and Glorioso’s Deli. Finally, you’ll stroll down the city’s former Gold Coast to end this tour at the Oak Leaf Trail on Prospect Avenue, giving you the opportunity to continue your Milwaukee adventure independently on the Lake Line Trail. This family-friendly tour is an easy stroll, with the option to pop inside some of the city’s most interesting churches. Come hungry, there are plenty of opportunities to grab snacks, or discover your new favorite restaurant along the route.

If you've already seen most of the sights of Milwaukee, get a different perspective on the city with this haunted history walking tour of Lake Geneva. As you stroll in a small group, your guide will fill you in on all the colorful history and characters, from haunted mansions and vengeful spirits to lake monsters and more.

Get to know one of Milwaukee‘s most haunted neighborhoods, Westown, and discover why Marquette University is considered one of the nation‘s most haunted schools. On this self-guided walking tour, you‘ll visit eleven haunted locations and hear some of Milwaukee‘s most spook-tacular tales! Starting in front of the Milwaukee Public Museum, you‘ll stroll around Marquette Campus and along Wisconsin Ave to Straz Tower, where our tour ends. Along the way, you‘ll meet some of Milwaukee‘s most famous ghosts, including a professor who continues to report to work, and a home-proud beer baron. You‘ll also see the site of one of the city‘s most notorious murders. Lace up your shoes and join me in discovering the haunted side of this historic neighborhood. This family-friendly hour-long walk does contain content that may be disturbing, including details of murders, mentions of suicide and accidental deaths. Please use caution when selecting this tour for very young or sensitive audiences.

The Historic Third Ward was the first stop for many of Milwaukee's European immigrants, particularly the Irish and later the Italians. Close to cheap housing and available jobs, these new arrivals created close-knit communities. Like most major industrial cities, the Third Ward had a significant and destructive fire in 1892, which reshaped the landscape to much of what you see today. In the 1970s, this area experienced a resurgence that transformed factories and warehouses into condos and mixed adaptive reuse. On this tour, learn about the neighborhood landscape as well as the Irish and Italian immigrants as well as the impact of the LGBTQ+ community and other residents. Stops include the Milwaukee Public Market (2005), Milwaukee Institute of Art and Design (MIAD) (1974), and Commission Row (1894). This walking tour is 1 mile in length. Travelers are recommended to bring (weather permitting): good walking shoes, water, sunscreen, and/or umbrella.

West of the Milwaukee River, you’ll find the historic arts and entertainment district of Downtown. Today, the area known as Westown includes several theaters and arts venues as well as sports arenas, the Baird Convention Center, and several historic hotels. Also in the district is the multi-block Grand Avenue Mall (1982), now redeveloped into The Avenue (2018) with updated food hall and shopping. This tour will explore the recent transformation of several historic buildings into mixed-use development with apartments, new coffee shops, and gallery spaces, and the reinvigoration of office space. Included on the tour are Milwaukee’s large blue building, the Reuss Federal Plaza, now known as 310W (1983), the historic Hotel Wisconsin (1913), and the Pabst Theater (1895). This walking tour is 1.4 miles in length. We recommend that travelers bring (weather permitting): good walking shoes, water, sunscreen, and/or an umbrella.

Like many communities in the industrial Midwest, Milwaukee’s ecological legacy has a significant period of pollution. Thankfully, in the late 1980s & early 1990s, driven by Mayor John Norquist and others, Milwaukee dedicated resources to water clean up and the reinvigoration of the buildings along the Milwaukee River. This reinvestment included the creation of a public-private partnership known as the Riverwalk (1993). Today, the Riverwalk extends 3.1 miles along both sides of the Milwaukee River, from the site of the former North Avenue Dam, through Downtown and the Historic Third Ward to Lake Michigan. The tour will explore the industries and early city growth that impacted the river so greatly and also a number of the historic buildings along the way. You’ll also learn about some of the temporary and permanent public art on display. This walking tour is 1.2 miles in length. We recommend that travelers bring: good walking shoes, water, sunscreen, and/or umbrella.

On this private tour, you completely customize your route, pick your preferred duration, and select your exact sightseeing stops across Milwaukee. Skip the rigid schedules of standard group excursions and build your ideal urban trek alongside an expert local storyteller. Whether you want to explore 19th-century German immigration landmarks, marvel at modern lakefront architecture, or uncover the industrial revitalization of the historic warehouse districts, you call the shots. Your dedicated guide adapts the route and stories to match your group perfectly. Your Customization Choices: Choose your route: Focus on old-world civic history or sleek modern architecture. Pick your duration: Select a 2, 3, or 4-hour walk to match your schedule. Select your stops: Handpick locations like the Milwaukee Art Museum or Third Ward. Please note: Your exact itinerary may vary from the standard plan depending on the custom path and options you select at booking.